- Catalyst- and Substrate-Dependent Chemodivergent Reactivity of Stabilised Sulfur Ylides with Salicylaldehydes
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Stabilised sulfur ylides are synthetically appealing compounds, which reactivity under Br?nsted acid catalysis has been poorly explored. Herein, we report a new catalyst- and substrate- dependent chemodivergent reaction between stabilised sulfur ylides and salicylaldehydes, leading to the (suprising) formation of 2H-chromenes or dihydrobenzofurans products. Particular attention was set on the unusual mechanisms involved. Two unique reaction routes including two ylide units in the reactions are proposed. These pathways were validated by performing a selectivity switch in some cases, enabled by the modulation of the nucleophilicity of the sulfur ylide, and by the loading of the Br?nsted acid catalyst in the reaction. (Figure presented.).
- Denisa Bisag, Giorgiana,Ruggieri, Silvia,Fochi, Mariafrancesca,Bernardi, Luca
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- Direct Synthesis of α-Fluoro-α-Triazol-1-yl Ketones from Sulfoxonium Ylides: A One-Pot Approach
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The work reported herein showcases a new route to access α-fluoro-α-triazol-1-yl ketones from sulfoxonium ylides via α-azido-α-fluoro ketone intermediates. In a one-pot, two-step sequence, the ketosulfoxonium reactant initially undergoes insertion of F+ a
- Burtoloso, Antonio Carlos Bender,Day, David Philip,Mora Vargas, Jorge Andrés
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- Mechanism and Selectivity of Cyclopropanation of 3-Alkenyl-oxindoles with Sulfoxonium Ylides Catalyzed by a Chiral N, N′-Dioxide-Mg(II) Complex
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The mechanism and stereoselectivity of an asymmetric cyclopropanation reaction between 3-alkenyl-oxindole and sulfoxonium ylide catalyzed by a chiral N,N′-dioxide-Mg(II) complex were explored using the B3LYP-D3(BJ) functional and the def2-TZVP basis set.
- Lv, Cidan,Meng, Xiangxiang,Wang, Min,Zhang, Yan,Hu, Changwei,Kim, Chan Kyung,Su, Zhishan
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- Synthesis of Isatin-Hydrazones from 3-Diazo Oxindoles and Sulfoxonium Ylides under Catalyst- and Additive-Free Conditions
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A facile synthesis of isatin-hydrazones from 3-diazo oxindoles and sulfoxonium ylides under catalyst- and additive-free conditions is described. A plausible reaction pathway is proposed for the transformation, in which diazo compounds play as electrophile
- Tian, Yu,Zhang, Zunting,Wang, Tao
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- Synthesis of Pyrazolo[1,2-a]cinnolines via Rhodium(III)-Catalyzed [4+2] Annulation Reactions of Pyrazolidinones with Sulfoxonium Ylides
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A method to synthesize pyrazolo[1,2-a]cinnolines via rhodium(III)-catalyzed C?H activation of pyrazolidinones and subsequent [4+2] annulation of sulfoxonium ylides was developed. 5-Substituted or 5,10-disubstituted pyrazolo[1,2-a]cinnolines could be obtained by slightly adjusting the reaction conditions. Gram-scale synthesis and practical transformations proved the practicability of this method. The mechanism of this method was proposed in the article on the basis of preliminary mechanistic results and previous reports. This method features simplified operation, metal-oxidant free, and readily available reactants. (Figure presented.).
- Fang, Feifei,Han, Xu,Hu, Shulei,Liu, Hong,Saidahmatov, Abdusaid,Wang, Jiang,Wang, Yong,Xie, Xiong
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supporting information
p. 3311 - 3317
(2021/07/02)
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- Synthesis of Sulfoxonium Ylides from Amides by Selective N-C(O) Activation
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The direct synthesis of sulfoxonium ylides from amides by selective N-C(O) cleavage is presented. The reaction proceeds through the nucleophilic addition of dimethylsulfoxonium methylide to the amide bond in acyclic twisted amides under exceedingly mild r
- Rahman, Md. Mahbubur,Szostak, Michal
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p. 4818 - 4822
(2021/06/28)
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- Rhodium(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides
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A novel protocol for Rh(iii)-catalyzed switchable C-H acylmethylation and annulation of 2,2′-bipyridine derivatives with sulfoxonium ylides is reported. This protocol provides a facile approach to synthesize structurally diverse acylmethylated 2,2′-bipyridine derivatives and acyl pyrido[2,3-a]indolizines with a broad range of functional group tolerance.
- Chen, Chen,Chen, Mengjia,Meng, Haifang,Wang, Yani,Yang, Fang,Zhu, Bolin
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supporting information
p. 4268 - 4271
(2021/05/31)
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- Hydroxyl-Directed Ruthenium-Catalyzed peri-Selective C-H Acylmethylation and Annulation of Naphthols with Sulfoxonium Ylides
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Herein, we report a highly efficient ruthenium-catalyzed peri-selective C(sp2)-H acylmethylation of 1-naphthols with α-carbonyl sulfoxonium ylides by utilizing hydroxyl as a weakly coordinating directing group. This new method imparts good reactivity, excellent chemo- and regioselectivity, and broad functional group tolerance and involves mild reaction conditions. The C-H acylmethylated products can be readily cyclized into fluorescent annulated pyrans by a one-pot process.
- Ma, Wenbo,Tan, Yuqiang,Wang, Yang,Li, Zhiyi,Li, Zheyu,Gu, Linghui,Mei, Ruhuai,Cheng, An
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supporting information
p. 6200 - 6205
(2021/08/23)
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- Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides
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Disclosed herein is an efficient Ag-catalyzed [4 + 1] heteroannulation reaction of enamides with α-carbonyl sulfoxonium ylides. The diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline derivatives. The synthetic utility of the resultant tetra-substituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.
- Liu, Rui-Hua,Shan, Qi-Chao,Gao, Ya,Loh, Teck-Peng,Hu, Xu-Hong
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supporting information
p. 1411 - 1414
(2020/10/29)
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- Regioselective and Chemodivergent Synthesis of Azulenolactones and Azulenolactams from Rhodium(III)-Catalyzed Reactions of Azulenecarboxamides with Sulfoxonium Ylides
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A regioselective and chemodivergent synthetic approach for azulenolactones and azulenolactams as a new scaffold was demonstrated through Rh(III)-catalyzed reaction of N-methoxyazulene-1-carboxamides with sulfoxonium ylides. Sulfoxonium ylides that act as a precursor of secondary carbene was described, leading to the selective formation of azulenolactones and azulenolactams bearing two substituents on a newly introduced double bond. This method demonstrated functionalization of less reactive 2-position of azulene to overcome the natural reactivity. (Figure presented.).
- Lee, Seung Cheol,Son, Jeong-Yu,Kim, Jin Young,Eom, Hyeonsik,Jang, Seong Bin,Lee, Phil Ho
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p. 512 - 524
(2020/11/30)
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- Synthetic method of imidazopyridine compounds
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The invention provides a novel method for synthesizing imidazopyridine compounds. According to the invention, aminopyridine compounds and sulfur ylide are used as original reaction substrates, iron phthalocyanine (FeIIPc) is used as a catalyst, and a series of the imidazopyridine compounds are obtained under the condition that the advantages of mildness, greenness, high efficiency, wide substrateuniversality and the like are achieved.
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Paragraph 0051-0053
(2021/03/24)
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- Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas
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Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.
- Chen, Yuncan,Lv, Shan,Lai, Ruizhi,Xu, Yingying,Huang, Xin,Li, Jianglian,Lv, Guanghui,Wu, Yong
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supporting information
p. 2555 - 2558
(2021/03/17)
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- Synthesis method of benzofuran compound
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The invention belongs to the field of organic chemical synthesis, and particularly relates to a synthesis method of a benzofuran compound. According to the invention, the reaction system adopts economical and efficient iron phthalocyanine as a catalyst, a
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Paragraph 0050-0052
(2021/05/19)
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- Ruthenium-Catalyzed Alkylation of Cyclopropanols with Sulfoxonium Ylides via C-C Bond Cleavage: Formation of Diverse 1,5-Diketones
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A novel ruthenium-catalyzed alkylation of cyclopropanols with sulfoxonium ylides has been developed that affords diverse 1,5-diketones with good efficiency and broad substrate scope. To illustrate the synthetic applications of the obtained 1,5-diketones, aldol and cyclization reactions have been investigated. Preliminary mechanistic studies suggest that this process involves a sequential C C activation and carbene migratory insertion.
- Huang, Xin,Li, Jianglian,He, Hua,Yan, Kaichuan,Lai, Ruizhi,Luo, Yi,Guan, Mei,Wu, Yong
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supporting information
p. 779 - 787
(2021/10/29)
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- Iridium-Catalyzed [4+2] Annulations of β-Keto Sulfoxonium Ylides and o-Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives
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A synthetic method for quinoxaline derivatives from the [4+2] annulation of β-keto sulfoxonium ylides and o-phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional-group compatibility. Moreover, this cyclization strategy was successfully applied in late-stage modification for structurally complex bioactive compounds.
- Che, Tong,Kang, Hua-Jie,Peng, Dongming,Shu, Bing,Song, Jia-Lin,Wang, Xiao-Tong,Xie, Hui,Zhang, Luyong,Zhang, Shang-Shi,Zhong, Mei
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- Synthesis method of alpha, alpha, beta-tricarbonyl sulfur ylide compound
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The invention relates to a method for synthesizing an alpha, alpha, beta-tricarbonyl sulfur ylide compound, and the method comprises the following steps of: reacting in an organic solvent under the action of a catalyst by taking sulfur oxide ylide shown a
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Paragraph 0022-0027
(2020/03/17)
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- Copper-Catalyzed Annulation or Homocoupling of Sulfoxonium Ylides: Synthesis of 2,3-Diaroylquinolines or α,α,β-Tricarbonyl Sulfoxonium Ylides
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An unprecedented copper-catalyzed reaction of sulfoxonium ylides and anthranils is reported that enables an easy access to 2,3-diaroylquinolines through a [4+1+1] annulation. Copper-catalyzed homocoupling of sulfoxonium ylides provided α,α,β-tricarbonyl sulfoxonium ylides, which provides a strategy to extend the carbon chain through C-C bond formation. The utility of the products as well as the mechanistic details of the process are presented.
- Zhu, Shuai,Shi, Kai,Zhu, Hao,Jia, Zhe-Kang,Xia, Xiao-Feng,Wang, Dawei,Zou, Liang-Hua
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supporting information
p. 1504 - 1509
(2020/03/03)
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- Rh(III)-Catalyzed [3 + 3] Annulation Reaction of Cyclopropenones and Sulfoxonium Ylides toward Trisubstituted 2-Pyrones
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A new Rh(III)-catalyzed [3 + 3] annulation reaction between cyclopropenones and β-ketosulfoxonium ylides has been reported, enabling metal carbene insertion to access a wide range of trisubstituted 2-pyrones with moderate to excellent yields via C-C single-bond cleavage, in which sulfoxonium ylides serve as potential safe precursors of metal carbenes. This reaction occurred under redox-neutral conditions with a broad substrate scope.
- Zhou, Peng,Yang, Wei-Tao,Rahman, Anis Ur,Li, Guigen,Jiang, Bo
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p. 360 - 366
(2019/11/14)
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- Rhodium-catalyzed regioselective C(sp2)–H bond activation reactions of N-(hetero)aryl-7-azaindoles and cross-coupling with α-carbonyl sulfoxonium ylides
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We described a protocol for rhodium-catalyzed C(sp2)–H bond activation reactions of N-(hetero)aryl-7-azaindoles and cross-coupling with α-carbonyl sulfoxonium ylides. In the C–H activation reaction, the 7-azaindole moiety acts as a directing gr
- Tian, Yan,Kong, Xian-Qiang,Niu, Jie,Huang, Yi-Bo,Wu, Zhao-Hua,Xu, Bo
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supporting information
(2020/01/24)
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- Rh(III)-Catalyzed Reaction of α-Carbonyl Sulfoxonium Ylides and Alkenes: Synthesis of Indanones via [4 + 1] Cycloaddition
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The synthesis of indanone derivatives by the Rh(III)-catalyzed reaction of α-carbonyl sulfoxonium ylides with activated alkenes is reported. The reaction shows a high tolerance for functional groups and furnishes a variety of substituted indanone derivati
- Ando, Shunsuke,Chatani, Naoto,Kommagalla, Yadagiri
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supporting information
p. 1375 - 1379
(2020/03/13)
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- Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water
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Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.
- Xu, Yingying,Huang, Xin,Lv, Guanghui,Lai, Ruizhi,Lv, Songyang,Li, Jianglian,Hai, Li,Wu, Yong
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supporting information
p. 4635 - 4638
(2020/07/04)
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- Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives
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A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.
- Wang, Fei,Liu, Bo-Xi,Rao, Weidong,Wang, Shun-Yi
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supporting information
p. 6600 - 6604
(2020/09/02)
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- Synthesis of C6-Substituted Isoquinolino[1,2- b]quinazolines via Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides
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We report the synthesis of C6-substituted isoquinolino[1,2-b]quinazolinones via rhodium(III)-catalyzed C-H annulation with sulfoxonium ylides and evaluation of the cytotoxic activity of the scaffold. This C-H activation approach enables the most straightforward and convergent synthesis of C6-substituted isoquinolino[1,2-b]quinazolines reported to date. This operationally simple method is compatible with a wide variety of the sulfoxonium ylide and arene C-H activation coupling partners, permitting access to diverse isoquinolino[1,2-b]quinazolines. This method shows a high atom economy, generating H2O and dimethyl sulfoxide (DMSO) as by-products. This method is scalable and operates with exquisite N-lactam cyclization selectivity, thus enabling expedient access to new heterocyclic analogues featuring promising cytotoxic properties.
- Chen, Di,Kang, Yifan,Ma, Yangmin,Szostak, Michal,Wang, Xiaogang,Zhang, Jin
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p. 3192 - 3201
(2020/03/23)
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- Rhodium-catalyzed tandem acylmethylation/annulation ofN-nitrosoanilines with sulfoxonium ylides for the synthesis of substituted indazoleN-oxides
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An atom-economical protocol for synthesizing indazoleN-oxides from readily availableN-nitrosoanilines and sulfoxonium ylides through the rhodium(iii)-catalyzed C-H activation and cyclization reaction is described here. This protocol employs nitroso as a traceless directing group. The transformation features powerful reactivity, tolerates various functional groups, and proceeds with moderate to good yields under an ambient atmosphere, providing a straightforward approach to access structurally diverse and valuable indazoleN-oxide derivatives. Importantly, this new annulation process represents a hitherto unobserved reactivity pattern for theN-nitroso group.
- Cui, Xin-F,Huang, Guo-Sh
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supporting information
p. 4014 - 4018
(2020/06/09)
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- Br?nsted Acid-Promoted Diastereoselective [4+1] Cyclization Reaction of Enamides and Sulfoxonium Ylides
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A metal-free synthesis of trisubstituted trans-oxazolines using enamides and sulfoxonium ylides was developed in this study. A [4+1] cyclization reaction was realized by the formation of C?C and C?O bonds under mild conditions, wherein the reaction was catalyzed by HClO4. This strategy produced trans-oxazolines in good yields with considerable diastereoselective control and is sufficient for large-scale synthesis. (Figure presented.).
- Luo, Nan,Zhan, Zhenzhen,Ban, Zihui,Lu, Guoqiang,He, Jianping,Hu, Fangpeng,Huang, Guosheng
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supporting information
p. 3126 - 3130
(2020/07/06)
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- Ruthenium-Catalyzed Synthesis of Pyrrolo[1,2- A [quinoxaline Derivatives from 1-(2-Aminophenyl)pyrroles and Sulfoxonium Ylides
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A ruthenium-catalyzed [5+1] annulation of 1-(2-aminophenyl)pyrroles with α-carbonyl sulfoxonium ylides is reported. This reaction provides a one-step method for synthesizing pyrrolo[1,2- A [quinoxaline derivatives under ambient conditions. The system proceeds with a short reaction time and a high functional-group tolerance. Notably, this divergent protocol tolerates β-keto sulfoxonium ylides and can be applied to α-ester sulfoxonium ylides. A preliminary study was made of the mechanism of the reaction, and a reaction pathway is proposed.
- Cui, Xin-Feng,Hu, Fang-Peng,Huang, Guo-Sheng,Zhan, Zhen-Zhen,Zhou, Xiao-Qiang
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supporting information
p. 1205 - 1210
(2020/07/20)
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- Rhodium-catalyzed [4+1] annulation of sulfoxonium ylides: Sequential ortho-C[sbnd]H functionalization/carbonyl α-amination toward polycyclic quinazolinones
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A rhodium-catalyzed [4+1] annulation between 2-aryl quinazolin-4(3H)-ones and sulfoxonium ylides was developed, leading to 12-aroyl isoindolo[1,2-b]quinazolin-10(12H)-ones in moderate to good yields. This reaction proceeds with sequential ortho-C[sbnd]H functionalization of 2-aryl quinazolin-4(3H)-ones and an intramolecular rhodium-catalyzed α-amination of carbonyl to furnish the cyclization. This procedure was applied to access some 13-aroyl luotonin A derivatives whereby the direct construction of ring c.
- Wang, Chang,Qian, Peng-Cheng,Chen, Fan,Cheng, Jiang
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supporting information
(2020/10/05)
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- Synthesis of 2-substituted indoles by iridium (III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines
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A highly regioselective synthesis of 2-substituted indoles was realized through Ir(III)-catalyzed C–]H functionalization of N-phenylpyridin-2-amines followed by the reaction with sulfoxonium ylides and intramolecular cyclization under mild conditions. The reaction completed with broad range of substrate scopes and gave various 2-substituted indoles in up to 98% yields.
- Zhang, Lei,Chen, Junyu,Chen, Jinkang,Jin, Licheng,Zheng, Xiangyun,Jiang, Xinpeng,Yu, Chuanming
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supporting information
p. 1053 - 1056
(2019/03/20)
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- Safe, Metal-Free, and Direct Synthesis of Dialkyl Acylmethylidenehydrazine-1,1-dicarboxylates from Dimethylsulfoxonium Acylmethylides and Dialkyl Azodicarboxylates
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N-Acylhydrazones are versatile electrophiles for the synthesis of nitrogen-containing compounds. Dialkyl acylmethylidenehydrazine-1,1-dicarboxylates are a class of N-acylhydrazones and were prepared efficiently from dimethylsulfoxonium acylmethylides and dialkyl azodicarboxylates. The reaction is temperature-controlled, generating tetraalkyl 3,6-diacyl-1,2,4,5-tetrazinane-1,2,4,5-tetracarboxylates as major products accompanied by dialkyl acylmethylidenehydrazine-1,1-dicarboxylates as byproducts at low temperature, or dialkyl acylmethylidenehydrazine-1,1-dicarboxylates only at high temperature. The current direct synthetic method is a safe and transition-metal-free route for the synthesis of dialkyl acylmethylidenehydrazine-1,1-dicarboxylates. (Figure presented.).
- Zhou, Bingnan,Dong, Jun,Xu, Jiaxi
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supporting information
p. 4540 - 4548
(2019/08/30)
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- Synthesis of functionalized thietanes via electrophilic carbenoid-induced ring expansion of thiiranes with sulfonium acylmethylides as carbene precursors
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Various functionalized thietanes were prepared from thiiranes via an electrophilic ring expansion with rhodium carbenoids as electrophiles generated from safe and readily accessible dimethylsulfonium acylmethylides. The reaction appears to proceed through electrophilic metallocarbenoid-induced activation of thiiranes, nucleophilic ring-opening of the activated thiiranes with dimethyl sulfide as a transient nucleophile, and nucleophilically intramolecular cyclization. The Umpolung from the nucleophilic ylides to the electrophilic carbenoids plays an important role in both the activation and ring opening of thiiranes and subsequent cyclization. The current method provides a new strategy for the efficient preparation of functionalized thietanes from readily available thiiranes.
- Dong, Jun,Du, Hongguang,Xu, Jiaxi
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p. 10724 - 10739
(2019/09/30)
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- Synthesis of Furoxans and Isoxazoles via Divergent [2 + 1 + 1 + 1] Annulations of Sulfoxonium Ylides and tBuONO
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We have presented a simple and new method for the divergent assembly of furoxans and isoxazoles in which the [2 + 1 + 1 + 1] annulation reaction of sulfoxonium ylides is reported for the first time. When the reaction was performed using tBuONO
- Tang, Zhonghe,Zhou, Yao,Song, Qiuling
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supporting information
p. 5273 - 5276
(2019/09/03)
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- Ruthenium(II)-Catalyzed Homocoupling of Weakly Coordinating Sulfoxonium Ylides via C?H Activation/Annulations: Synthesis of Functionalized Isocoumarins
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Homocoupling of weakly coordinating sulfoxonium ylides was accomplished via ruthenium (II) catalyzed C?H activation process. This strategy provides a convenient, efficient and step-economic method to access 3-substituted isocoumarins with good functional
- Zhou, Ming-Dong,Peng, Zhen,Wang, He,Wang, Zhao-Hui,Hao, Da-Jin,Li, Lei
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supporting information
p. 5191 - 5197
(2019/11/13)
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- Iridium-catalyzed B-H bond insertion reactions using sulfoxonium ylides as carbene precursors toward α-boryl carbonyls
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An iridium-catalyzed B-H bond insertion reaction between borane adducts and sulfoxonium ylides to afford α-boryl carbonyls has been developed. The starting materials are safe and readily available. In addition, analogues of sulfoxonium ylides, such as sul
- Li, Jianglian,He, Hua,Huang, Mengyi,Chen, Yuncan,Luo, Yi,Yan, Kaichuan,Wang, Qiantao,Wu, Yong
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supporting information
p. 9005 - 9008
(2019/11/14)
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- Rhodium(III)-Catalyzed Annulative Coupling of Sulfoxonium Ylides and Allenoates: An Arene C-H Activation/Cyclopropanation Cascade
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Rhodium(III)-catalyzed annulative coupling of sulfoxonium ylides with allenoates was achieved, forming highly functionalized cyclopropanes with a quaternary carbon center by means of the sulfoxonium ylide functionality as a traceless bifunctional directin
- Lou, Jiang,Wang, Quannan,Zhou, Yong-Gui,Yu, Zhengkun
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supporting information
p. 9217 - 9222
(2019/11/19)
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- Direct Access to 1,1-Dicarbonyl Sulfoxonium Ylides from Aryl Halides or Triflates: Palladium-Catalyzed Carbonylation
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The synthesis of 1,1-dicarbonyl sulfoxonium ylides by palladium-catalyzed carbonylation of aryl halides or triflates with α-carbonyl sulfoxonium ylides has been developed for the first time. This method provides a general approach to synthetically useful 1,1-dicarbonyl sulfoxonium ylides in high efficiency. The protocol displays a wide substrate scope, showing that the resulting 1,1-dicarbonyl sulfoxonium ylides have been converted into the corresponding 1,3-dicarbonyl compounds.
- Yuan, Yang,Wu, Xiao-Feng
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supporting information
p. 5310 - 5314
(2019/09/06)
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- Rhodium-Catalyzed Reaction of Sulfoxonium Ylides and Anthranils toward Indoloindolones via a (4 + 1) Annulation
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A rhodium-catalyzed annulation between aroyl sulfoxonium ylides and anthranils has been developed to synthesize 10H-indolo[1,2-a]indol-10-one derivatives. This reaction started with an unpredented (4 + 1) annulation toward N-(2-formylphenyl) indolones, pr
- Wu, Xiaopeng,Xiao, Yan,Sun, Song,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 6653 - 6657
(2019/09/12)
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- Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides
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Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.
- Cui, Xin-Feng,Ban, Zi-Hui,Tian, Wa-Fa,Hu, Fang-Peng,Zhou, Xiao-Qiang,Ma, Hao-Jie,Zhan, Zhen-Zhen,Huang, Guo-Sheng
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supporting information
p. 240 - 243
(2019/01/10)
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- Rhodium-catalyzed C–H activation/cyclization of enaminones with sulfoxonium ylides toward polysubstituted naphthalenes
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A rhodium-catalyzed ortho-C–H functionalization and annulation between enaminones and sulfoxonium ylides was developed, affording a series of multi-substituted naphthalenes in good to moderate yields with excellent functional group compatibility. The proc
- Wang, Zhenlian,Xu, Huang
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supporting information
p. 664 - 667
(2019/02/06)
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- Synthesis of indoles and quinazolines via additive-controlled selective C-H activation/annulation of N -arylamidines and sulfoxonium ylides
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Selective synthesis of indole and quinazoline products was achieved through a precise control of the C-H activation/annulation by changing the additives from NaOAc to CuF2/CsOAc. This strategy constructs indole and quinazoline scaffolds efficie
- Lai, Ruizhi,Wu, Xiaohua,Lv, Songyang,Zhang, Chen,He, Maoyao,Chen, Yuncan,Wang, Qiantao,Hai, Li,Wu, Yong
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supporting information
p. 4039 - 4042
(2019/04/10)
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- Acid-catalyzed synthesis of imidazole derivatives via N-phenylbenzimidamides and sulfoxonium ylides cyclization
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A straightforward method to synthesize imidazole derivatives from amidines and sulfoxonium ylides catalyzed by acids is reported in this study. Specifically, catalyzed by trifluoroacetic acid in DCE solvents can improve synthesis efficiency under metal-fr
- Tian, Yuan,Qin, Mingda,Yang, Xueying,Zhang, Xueguo,Liu, Yafeng,Guo, Xin,Chen, Baohua
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supporting information
p. 2817 - 2823
(2019/04/13)
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- Rhodium(III)-catalyzed [4+2] annulation via C-H activation: Synthesis of multi-substituted naphthalenone sulfoxonium ylides
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A convenient Rh(III)-catalyzed C-H activation and cascade [4+2] annulation for the synthesis of naphthalenone sulfoxonium ylides has been developed. This method features perfect regioselectivity, mild and redox-neutral reaction conditions, and broad substrate tolerance with good to excellent yields. Preliminary mechanistic experiments were conducted and a plausible reaction mechanism was proposed. The new type naphthalenone sulfoxonium ylides could be further transformed into multi-substituted naphthols, which demonstrates the practical utility of this methodology.
- Song, Xiaohan,Han, Xu,Zhang, Rui,Liu, Hong,Wang, Jiang
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- Iridium-Catalyzed Three-component Coupling Reaction of Carbon Dioxide, Amines, and Sulfoxonium Ylides
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The first iridium-catalyzed three-component coupling reaction of carbon dioxide, amines, and sulfoxonium ylides has been developed, providing an efficient and straightforward method for the construction of a range of structurally diverse O-β-oxoalkyl carbamates in moderate to excellent yields. This novel protocol features the use of readily available substrates, wide substrate scope, and good functional group tolerance. Moreover, the phosgene-free strategy was successfully applied to the synthesis of a potential antitumor agent.
- Jiang, Huanfeng,Zhang, Hao,Xiong, Wenfang,Qi, Chaorong,Wu, Wanqing,Wang, Lu,Cheng, Ruixiang
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supporting information
p. 1125 - 1129
(2019/05/16)
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- Synthesis of Esters from Stable and Convenient Sulfoxonium Precursors under Catalyst- And Additive-Free Conditions
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A convenient and efficient procedure for the construction of esters from stable sulfoxonium ylides and alcohols has been developed. This protocol presents a broad substrate scope and good yields of the desired esters can be isolated. Notably, no catalyst, oxidant, base or any other additive is required.
- Wu, Xiao-Feng,Yuan, Yang
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supporting information
p. 1820 - 1824
(2019/09/09)
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- Water-mediated C-H activation of arenes with secure carbene precursors: The reaction and its application
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A water-mediated C-H activation using sulfoxonium ylides is reported, providing a general, green and step-economic approach to construct a C-C bond and varieties of useful N-heterocycle scaffolds. Notably, the "water-mediated" activation, in contrast to that in organic solvents, shows great potential in pharmaceutical, biochemistry and chemical industries.
- Guo, Li,Lai, Ruizhi,Lv, Songyang,Nie, Ruifang,Wang, Qiantao,Wu, Yong,Xu, Yingying
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supporting information
p. 11418 - 11421
(2019/09/30)
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- Rhodium(III)-Catalyzed C-H Activation of Benzoylacetonitriles and Cyclization with Sulfoxonium Ylides to Naphthols
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Rhodium(III)-Catalyzed C?H activation of benzoylacetonitriles in coupling with sulfoxonium ylides was developed to synthesize diversified substituted naphthols, in which aryl, heterocyclic and alkyl groups in sulfoxonium ylides are tolerated. Intriguingly, we have further implemented transformation for 1-naphthols to give some intriguing fused tricyclic compounds and derivatives of propranolol, which demonstrate the practical utility of this methodology. (Figure presented.).
- Zhou, Chaofan,Fang, Feifei,Cheng, Yilang,Li, Yazhou,Liu, Hong,Zhou, Yu
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supporting information
p. 2546 - 2551
(2018/05/16)
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- Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones
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A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into α-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.
- Talero, Alexánder Garay,Martins, Bruna Sim?es,Burtoloso, Antonio C. B.
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supporting information
p. 7206 - 7211
(2018/11/23)
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- Ruthenium (II)-Catalyzed Oxidant-Free Coupling/Cyclization of Benzimidates and Sulfoxonium Ylides to Form Substituted Isoquinolines
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A ruthenium-catalyzed direct mono-C?H functionalization/annulation cascade reaction of benzimidates and sulfoxonium ylides has been developed. The reaction proceeds smoothly with a broad range of substrates, giving access to a variety of isoquinoline deri
- Shi, Xinxia,Wang, Rongchao,Zeng, Xiaofei,Zhang, Yilan,Hu, Huiling,Xie, Chunsong,Wang, Min
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supporting information
p. 4049 - 4053
(2018/09/21)
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- Rhodium(III)-catalyzed chemodivergent annulations between: N-methoxybenzamides and sulfoxonium ylides via C-H activation
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Chemodivergent and redox-neutral annulations between N-methoxybenzamides and sulfoxonium ylides have been realized via Rh(iii)-catalyzed C-H activation. The sulfoxonium ylide acts as a carbene precursor, and coupling occurs under acid-controlled condition
- Xu, Youwei,Zheng, Guangfan,Yang, Xifa,Li, Xingwei
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supporting information
p. 670 - 673
(2018/01/28)
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- Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes
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A rhodium-catalyzed annulation between ethyl benzimidates and α- aroyl sulfur ylides was developed, affording a series of pyrano[4,3,2-ij]isoquinoline derivatives in moderate to good yields with good functional group compatibility. The procedure featured
- Wu, Xiaopeng,Xiong, Hao,Sun, Song,Cheng, Jiang
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supporting information
p. 1396 - 1399
(2018/03/09)
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- Rh(III)-catalyzed [4?+?1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides toward 3-acyl-(2H)-indazoles
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A Rh(III)-catalyzed [4 + 1]-annulation of azobenzenes with α- carbonyl sulfoxonium ylides was developed to access 2H-indazoles in moderate to excellent yields with good functional group compatibilities. It proceeded with the sequential insertion of the Rh(III) carbene to the C?H bond and cyclization steps, where sulfoxonium ylides served as efficient and stable carbene precursor.
- Zhu, Jiawei,Sun, Song,Cheng, Jiang
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supporting information
p. 2284 - 2287
(2018/05/23)
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