- One-pot synthesis of sulfonylhydrazones from sulfonyl chloride, hydrazine hydrate and vinyl azide in water
-
A facile and eco-friendly protocol for the synthesis of sulfonylhydrazones from sulfonyl chlorides, hydrazine hydrate and vinyl azides was developed. The unique advantage of this approach is that desired products can be obtained efficiently in water, which meets the requirements of green chemistry and provides good perspectives for the sustainable production of new drug candidate. Also, this reaction proceeded in moderate to good yields with a wide tolerance of functional groups.
- Luo, Mengqiang,Wang, Hai,Ren, Xiaorong,Lu, Ruijuan,Qi, Chenze,Zhang, Yaohong,Shen, Runpu
-
p. 2713 - 2722
(2021/03/19)
-
- Synthetic Routes for Heteroatom-Containing Alkylated/Arylated Polycyclic Aromatic Hydrocarbons
-
Synthetic routes for heteroatom-containing polycyclic aromatic hydrocarbons (H-PAHs) with alkyl and aryl substitution are demonstrated. Three H-PAHs, including heteroatom-containing rubicenes (H-rubicenes), angular-benzothiophenes (ABTs), and indenothioph
- Shi, Qinqin,Shi, Xiaosong,Feng, Changfu,Wu, Yishi,Zheng, Nan,Liu, Jie,Wu, Xiaoxi,Chen, Hao,Peng, Aidong,Li, Jianfeng,Jiang, Lang,Fu, Hongbing,Xie, Zengqi,Marder, Seth R.,Blakey, Simon B.,Huang, Hui
-
supporting information
p. 2924 - 2928
(2020/12/15)
-
- Pd-Catalyzed Coupling of Thioamides with N-Tosylhydrazones/Trapping by Esters Cascade Reaction
-
N,N-Disubstituted thioamides coupled with N-tosylhydrazones under Pd(TFA)2/tBuXPhos catalyst and NaOtBu, and the intermediates from palladium carbene migratory insertion containing β-hydrogen were trapped by intramolecular esters activated by BF3·Et2O ins
- Cai, Zhongliang,Yao, Zhi,Jiang, Liqin
-
supporting information
p. 311 - 316
(2021/01/26)
-
- Ru(ii)-Catalyzed, Cu(ii)-mediated carbene migratory insertion in the synthesis of trisubstituted pyrroles from isoxazoles
-
A convenient, “one-pot” synthesis of trisubstituted pyrrolesviaa Ru(ii)-catalyzed, Cu(ii)-mediated reaction of substituted isoxazoles with sulfonylhydrazones has been developed. A series of highly functionalized pyrroles are obtainedviaa synergistic forma
- Kumar, Pravin,Keshri, Santosh Kumar,Kapur, Manmohan
-
supporting information
p. 3428 - 3433
(2021/05/03)
-
- Copper-Catalyzed Regioselective Coupling of Tosylhydrazones and 2-Pyridones: A Strategy for the Production of N-Alkylated Compounds
-
The highly regioselective N-alkylation reaction of 2-pyridones was achieved through hydrazone chemistry, especially for substrates with bulky secondary alkyl groups. Described herein is a copper-catalyzed coupling reaction of pyridone derivatives with tosylhydrazones.
- Wu, Ye-Bin,Wu, You-Zhi,Wu, Jian,Xu, Dan,Jiang, Hui,Chang, Wen-Wu,Ma, Chang-You
-
p. 6918 - 6926
(2021/05/06)
-
- Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
-
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
- Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
-
p. 6007 - 6014
(2021/07/21)
-
- Visible-Light-Catalyzed in Situ Denitrogenative Sulfonylation of Sulfonylhydrazones
-
A photocatalyzed in situ denitrogenative sulfonylation of N-arylsulfonyl hydrazones has been developed. This transformation provides a low-carbon strategy to assemble arylalkyl sulfones in a stepwise denitrogenation/sulfonylation manner.
- Huang, Xiang,Chen, Xing,Xie, Haisheng,Tan, Zheng,Jiang, Huanfeng,Zeng, Wei
-
supporting information
p. 6784 - 6788
(2021/09/08)
-
- Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
-
We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved
- Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
-
p. 13664 - 13672
(2021/10/01)
-
- Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application
-
Synthesis, temperature-dependent NMR structure investigation and utilization of a new, stable and easily accessible aryl-diadamantylphosphine ligand family is reported. The bulky and electron-rich phosphorus center of the ligand enhances the catalytic activity of palladium in cross-coupling reactions of sterically demanding ortho-substituted aryl halides. In our study, we demonstrated the synthetic applicability of the new phosphine ligands in Buchwald-Hartwig and tosyl hydrazone coupling reactions.
- Sinai, ádám,Simkó, Dániel Cs.,Szabó, Fruzsina,Paczal, Attila,Gáti, Tamás,Bényei, Attila,Novák, Zoltán,Kotschy, András
-
supporting information
p. 1122 - 1128
(2020/03/03)
-
- Divergent Synthesis of Vinyl-, Benzyl-, and Borylsilanes: Aryl to Alkyl 1,5-Palladium Migration/Coupling Sequences
-
Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through-space metal/hydrogen shifts allow functionalization of C?H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5-palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl-, benzyl-, and borylsilanes, constituting a unique C(sp3)?H transformation based on a 1,5-palladium migration process.
- Han, Jie-Lian,Ju, Cheng-Wei,Qin, Ying,Zhao, Dongbing
-
supporting information
p. 6555 - 6560
(2020/03/03)
-
- Copper(I)/Bpy-Catalyzed C-2-H Benzylation of Quinazolin-4(3H)-ones with N-Tosylhydrazones
-
A general and efficient copper-catalyzed C–H benzylation reaction of quinazolin-4(3H)-ones with N-tosylhydrazones is reported. The formation of new C(sp3)–C(sp2) bonds through cross-coupling occurs at the electron-poor C-2 position of quinazolin-4(3H)-one and represents an exceedingly practical method to afford 2-benzylated quinazolin-4(3H)-ones in moderate to good yields under mild reaction conditions. A possible reaction mechanism for this transformation was proposed. This catalytic transformation has the potential to be an important synthetic application for the late-stage functionalization of advanced synthetic intermediates.
- Li, Fei,Gu, Xiao-Juan,Zeng, Chang-E.,Li, Xia,Liu, Bo,Huang, Guo-Li
-
supporting information
p. 2923 - 2928
(2020/05/16)
-
- Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
-
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
- Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
-
supporting information
p. 7524 - 7531
(2020/08/05)
-
- Sulfonylhydrazone derivative, and preparation method and application thereof
-
The invention discloses a sulfonylhydrazone derivative, and a preparation method and application thereof. The preparation method comprises the following step of taking olefin azide and sulfonyl hydrazine as starting materials to carry out a reaction, wher
- -
-
Paragraph 0036-0052; 0057
(2020/01/03)
-
- Pyrrolo-imidazo[1,2- A[pyridine Scaffolds through a Sequential Coupling of N-Tosylhydrazones with Imidazopyridines and Reductive Cadogan Annulation, Synthetic Scope, and Application
-
A new strategy for the construction of 3-phenyl-1H-pyrrolo-imidazo[1,2-a]pyridine backbone is described. The reaction starts from the coupling between N-tosylhydrazones and 2-chloro-3-nitroimidazo[1,2-a]pyridines leading to the formation of 3-nitro-2-(ary
- Zhang, Kena,El Bouakher, Abderrahman,Levaique, Helene,Bignon, Jerome,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
-
p. 13807 - 13823
(2019/10/16)
-
- Umpolung-like Cross-coupling of Tosylhydrazones with 4-Hydroxy-2-pyridones under Palladium Catalysis
-
Tosylhydrazones under palladium catalysis were found to perform cross-coupling reactions with 4-hydroxy-2-pyridones. The umpolung-like reactivity, between the α-carbon of tosylhydrazone and the 3-position of the heterocycle, which is observed in the obtai
- Katsina, Tania,Papoulidou, Kyriaki Eleni,Zografos, Alexandros L.
-
supporting information
p. 8110 - 8115
(2019/10/11)
-
- Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System
-
A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.
- Lamaa, Diana,Messe, Estelle,Gandon, Vincent,Alami, Mouad,Hamze, Abdallah
-
supporting information
p. 8708 - 8712
(2019/11/03)
-
- Copper(i)-catalyzed benzylation of triazolopyridine through direct C-H functionalization
-
A general and efficient copper-catalyzed benzylation reaction of triazolopyridine with N-tosylhydrazones was developed. This reaction forms a C(sp2)-C(sp3) bond through cross-coupling, and represents an exceedingly practical method t
- Reddy Lonka, Madhava,Zhang, Jinquan,Gogula, Thirupathi,Zou, Hongbin
-
p. 7455 - 7460
(2019/08/20)
-
- Lewis Acid Catalyzed [4 + 2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides
-
A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synt
- Wang, Chun-Ying,Han, Jia-Bin,Wang, Long,Tang, Xiang-Ying
-
p. 14258 - 14269
(2019/11/11)
-
- Synthesis of Multi-substituted Dihydropyrazoles by Copper-Mediated [4+1] Cycloaddition Reaction of N-Sulfonylhydrazones and Sulfoxonium Ylides
-
A general and expeditious approach for the copper mediated synthesis of multi-functionalized dihydropyrazoles from N-sulfonylhydrazones and sulfoxonium ylides has been achieved under aerobic oxidative conditions. The formal [4+1] cycloaddition reaction ex
- Hu, Sipei,Du, Shiying,Yang, Zuguang,Ni, Lingfang,Chen, Zhengkai
-
supporting information
p. 3124 - 3136
(2019/05/01)
-
- One-pot cascade synthesis of pyrazole based isosteres of valdecoxib by a [3+2] cycloaddition sequence and evaluation of their cox inhibitory activity
-
A series of 5-methyl-3,4-diaryl-substituted 1H-pyrazoles, N-isosteres of valdecoxib, was synthesized by a [3+2] cycloaddition/[1,5] sigmatropic rearrangement sequence starting from tosylhydrazine, aryl methyl ketones and terminal aryl alkynes bearing vari
- Roscales, Silvia,Bechmann, Nicole,Pietzsch, Jens,Kniess, Torsten
-
p. 416 - 428
(2019/07/31)
-
- I2/CuCl2-promoted one-pot three-component synthesis of aliphatic or aromatic substituted 1,2,3-thiadiazoles
-
An efficient I2/CuCl2-promoted one-pot three-component strategy for the construction of 1,2,3-thiadiazoles from aliphatic- or aromatic-substituted methyl ketones, p-toluenesulfonyl hydrazide, and potassium thiocyanate has been develo
- Wang, Can,Geng, Xiao,Zhao, Peng,Zhou, You,Wu, Yan-Dong,Cui, Yan-Fang,Wu, An-Xin
-
supporting information
p. 8134 - 8137
(2019/07/15)
-
- Copper-catalyzed one-pot coupling reactions of aldehydes (ketones), tosylhydrazide and 2-amino(benzo)thiazoles: An efficient strategy for the synthesis of N-alkylated (benzo)thiazoles
-
An efficient and practical C–N bond formation methodology for the synthesis of N-alkylated (benzo)thiazoles was developed, via the copper-catalyzed one-pot two-step reactions of 2-amino(benzo)thiazoles and aldehydes (ketones) with tosylhydrazide. This cross-coupling reaction proceeded smoothly and tolerated a broad range of functional groups (46 examples). A variety of functionalized N-alkylated (benzo)thiazoles were obtained in moderate to high yields. Notably, gram-scale synthesis of fanetizole (anti-inflammatory drug) was also realized through this protocol.
- Xie, Zengyang,Chen, Ruijiao,Ma, Mingfang,Kong, Lingdong,Liu, Jun,Wang, Cunde
-
-
- Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones
-
A chiral copper(I)-phosphoramidite complex efficiently catalyzed the asymmetric insertion of the carbenoids derived from N-tosyl hydrazones into alkyne C-H bonds to give the corresponding chiral alkynylated products in up to 77% yield and with up to 74% e
- Osako, Takao,Nagaosa, Makoto,Hamasaka, Go,Uozumi, Yasuhiro
-
supporting information
p. 2251 - 2256
(2018/10/20)
-
- Rapid Synthesis of N-Tosylhydrazones under Solvent-Free Conditions and Their Potential Application Against Human Triple-Negative Breast Cancer
-
Some N-tosylhydrazone derivatives were effectively synthesized under solvent-free conditions by using a grinding method at room temperature. The short reaction time, clean and mild process with simple workup and easy purification of the target compounds w
- Xie, Zengyang,Song, Yuying,Xu, Lujia,Guo, Yukun,Zhang, Min,Li, Limei,Chen, Kai,Liu, Xue
-
p. 977 - 983
(2018/11/27)
-
- Copper-Catalyzed Dehydrogenative Diels-Alder Reaction
-
A practical and effective copper-catalyzed dehydrogenative Diels-Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.
- Jiang, Bing,Liang, Qiu-Ju,Han, Yu,Zhao, Meng,Xu, Yun-He,Loh, Teck-Peng
-
supporting information
p. 3215 - 3219
(2018/06/11)
-
- Selective Construction of 2-Substituted Benzothiazoles from o-Iodoaniline Derivatives S8 and N-Tosylhydrazones
-
Selective construction of 2-substituted benzothiazoles from o-iodoaniline derivatives S8 and N-tosylhydrazone via a copper-promoted [3 + 1 + 1]-type cyclization reaction has been realized. In the protocol, the carbon atom on N-tosylhydrazone could be regulated to construct benzothiazole by changing the reaction system. Furthermore, the transformation has achieved the construction of multiple carbon-heteroatom bonds.
- Huang, Yubing,Zhou, Peiqi,Wu, Wanqing,Jiang, Huanfeng
-
p. 2460 - 2466
(2018/02/23)
-
- Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes
-
Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to in
- Parisotto, Stefano,Palagi, Lorenzo,Prandi, Cristina,Deagostino, Annamaria
-
supporting information
p. 5484 - 5488
(2018/03/27)
-
- Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates
-
A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.
- Huang, Hai,Denne, Johanna,Yang, Chou-Hsun,Wang, Haobin,Kang, Jun Yong
-
supporting information
p. 6624 - 6628
(2018/05/14)
-
- N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines
-
A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu
- Deshmukh, Dewal S.,Bhanage, Bhalchandra M.
-
supporting information
p. 4864 - 4873
(2018/07/15)
-
- Pyrazol compound with acetylcholin esterase inhibition activity as well as preparation method and application thereof
-
The invention discloses a pyrazol compound with acetylcholin esterase inhibition activity as well as a preparation method and application thereof. The pyrazol compound is 4-methyl-3-phenyl-1-p-toluenesulfonyl pyrazol, which can be obtained from material c
- -
-
Paragraph 0016; 0017; 0018
(2018/07/30)
-
- Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones
-
Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.
- Pang, Yue,He, Qiao,Li, Zi-Qi,Yang, Ji-Min,Yu, Jin-Han,Zhu, Shou-Fei,Zhou, Qi-Lin
-
supporting information
p. 10663 - 10668
(2018/09/06)
-
- Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones
-
A palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones is reported. The alkylpalladium intermediate coupled with the diazo compound, generating the second alkylpalladium species bearing two β-H, which generate
- Li, Jun,Chi, Xiaochen,Meng, Long,Jiao, Luyang,Shang, Wenhui,Wang, Ping,Zhang, Daopeng,Dong, Yunhui,Liu, Qing,Liu, Hui
-
supporting information
p. 7356 - 7360
(2018/10/24)
-
- N-Tosyl Hydrazone Precursor for Diazo Compounds as Intermediates in the Synthesis of Aluminum Complexes
-
The one-pot reaction of LAlH2 (1; L = HC(CMeNAr)2, Ar = 2,6-iPr2C6H3) with N-tosyl hydrazone as a precursor for preparing the diazo intermediate resulted in an aluminum compound with the composition L
- Liu, Yashuai,Ma, Xiaoli,Ding, Yi,Yang, Zhi,Roesky, Herbert W.
-
supporting information
p. 3839 - 3845
(2018/10/31)
-
- Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones to Access Iminofuran and 2(3H)-Furanone Derivatives
-
Efficient copper-catalyzed formal carbene migratory insertion into the olefinic C=C bonds of internal olefins, that is, α-oxo ketene N,S-acetals, has been achieved by means of N-tosylhydrazones of ketones as the carbene precursors. Iminofuran derivatives
- Huang, Fei,Liu, Zhuqing,Wang, Quannan,Lou, Jiang,Yu, Zhengkun
-
supporting information
p. 3660 - 3663
(2017/07/15)
-
- Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source
-
A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.
- Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng
-
p. 7621 - 7627
(2017/07/26)
-
- One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids
-
In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.
- Shen, Xu,Liu, Ping,Liu, Yang,Liu, Yan,Dai, Bin
-
supporting information
p. 785 - 793
(2017/01/16)
-
- Synthesis of Benzyltributylstannanes by the Reaction of N-Tosylhydrazones with Bu3SnH
-
An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.
- Qiu, Di,Wang, Shuai,Meng, He,Tang, Shengbo,Zhang, Yan,Wang, Jianbo
-
p. 624 - 632
(2017/04/26)
-
- Nickel-Catalyzed Direct Synthesis of Aryl Olefins from Ketones and Organoboron Reagents under Neutral Conditions
-
Nickel-catalyzed addition of arylboron reagents to ketones results in aryl olefins directly. The neutral condition allows acidic protons of alcohols, phenols, and malonates to be present, and fragile structures are also tolerated.
- Lei, Chuanhu,Yip, Yong Jie,Zhou, Jianrong Steve
-
supporting information
p. 6086 - 6089
(2017/05/08)
-
- Copper catalysed alkylation of heteroaryl chloride via migratory insertion of carbenes
-
Cross-coupling reaction involving Cu catalysed carbene migratory insertion with N-tosylhydrazones as the reaction partner with various substituted cyanuric chloride were studied, which has been recognized as a new type of cross-coupling reaction. Cu-carbe
- Mudaliar, Sulochana S.,Zala, Shailesh N.,Chikhalia, Kishor H.
-
supporting information
p. 142 - 148
(2017/08/08)
-
- Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes
-
An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from
- Ni, Meiyan,Zhang, Jianguo,Liang, Xiaoyu,Jiang, Yaojia,Loh, Teck-Peng
-
supporting information
p. 12286 - 12289
(2017/11/20)
-
- Synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde
-
The invention relates to a synthetic method for 2-methyl-4-carbonyl-2,4-diphenyl butyraldehyde. The synthetic method comprises the following steps: firstly adding 1,1-dimethoxy-N,N-dimethyl methylamine into a methylbenzene solution of acetophenone, after
- -
-
Paragraph 0026
(2018/01/14)
-
- A two-step continuous flow synthesis of 1,4-disubstituted 1,2,3-triazoles under metal- and azide-free conditions
-
A green, general and efficient I2/TBHP mediated synthetic method toward 1,4-disubstituted 1,2,3-triazoles via the reactions of acetophenones, tosylhydrazine and anilines within 35 min in a two-step continuous flow system has been developed. The
- Gu, Jiajia,Fang, Zheng,Yang, Zhao,Li, Xin,Zhu, Ning,Wan, Li,Wei, Ping,Guo, Kai
-
p. 89073 - 89079
(2016/10/03)
-
- Direct Synthesis of α-Alkoxy Ketones by Oxidative C–O Bond Formation
-
A convenient method to prepare α-alkoxy ketones has been developed by oxidative coupling of aryl methyl ketones and alcohols. With aqueous tert-butyl hydroperoxide (6.0 equiv.) as the oxidant, tetrabutylammonium iodide (20 mol-%) as the catalyst, and TsNHNH2(1.0 equiv.) as the additive, ketones underwent direct alkoxylation to give α-methoxy or α-ethoxy ketones in moderate to good yields.
- Yu, Hui,Xu, Yilan,Fang, Yan,Dong, Rui
-
p. 5257 - 5262
(2016/11/13)
-
- The microwave-assisted ortho-alkylation of azine N-oxides with N-tosylhydrazones catalyzed by copper(i) iodide
-
A copper catalyzed regioselective cross-coupling of N-tosylhydrazones with azine N-oxides to yield ortho-alkylated products in moderate to good yields is reported. The reaction is facilitated by microwave, takes place without any ligand, and uses inexpensive copper(i) iodide as the catalyst.
- Jha, Abadh Kishor,Jain, Nidhi
-
supporting information
p. 1831 - 1834
(2016/02/05)
-
- Palladium-Catalyzed One-Pot Synthesis of 5-(1-Arylvinyl)-1H-benzimidazoles: Overcoming the Limitation of Acetamide Partners
-
A new one-pot palladium-catalyzed process between N-tosylhydrazones, N-(dihalophenyl)-imidates, and amines was designed. This reaction involves Barluenga cross-coupling and N-arylation followed by cyclization to produce functionalized benzimidazoles. Duri
- Naret, Timothée,Retailleau, Pascal,Bignon, Jér?me,Brion, Jean-Daniel,Alami, Mouad,Hamze, Abdallah
-
supporting information
p. 1833 - 1847
(2016/06/09)
-
- One-step synthesis of sulfonamides from N-tosylhydrazones
-
The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moder
- Tsai, Andy S.,Curto, John M.,Rocke, Benjamin N.,Dechert-Schmitt, Anne-Marie R.,Ingle, Gajendrasingh K.,Mascitti, Vincent
-
supporting information
p. 508 - 511
(2016/02/18)
-
- Iron(III) phthalocyanine-chloride-catalyzed synthesis of sulfones from sulfonylhydrazones
-
In this study, sulfones are synthesized from sulfonylhydrazones catalyzed by iron(III) phthalocyanine chloride. This reaction offers broad substrate scope, occurs under mild conditions, utilized readily available reactants, and forms products in good-to-h
- Zhao, Jun-Long,Guo, Shi-Huan,Qiu, Jun,Gou, Xiao-Feng,Hua, Cheng-Wen,Chen, Bang
-
supporting information
p. 2375 - 2378
(2016/05/19)
-
- Copper-Mediated [3 + 2] Oxidative Cyclization Reaction of N-Tosylhydrazones and β-Ketoesters: Synthesis of 2,3,5-Trisubstituted Furans
-
The first attempt at utilizing N-tosylhydrazones as two-carbon synthons has been successfully achieved, which underwent a copper-mediated [3 + 2] oxidative cyclization reaction to afford 2,3,5-trisubstituted furans in moderate to good yields. The features of this method include inexpensive metal catalyst, readily available substrates, high regioselectivity, and convenient operation. The studies provide important approaches for further exploration of the powerful and diverse reaction abilities of N-tosylhydrazones.
- Huang, Yubing,Li, Xianwei,Yu, Yue,Zhu, Chuanle,Wu, Wanqing,Jiang, Huanfeng
-
p. 5014 - 5020
(2016/07/06)
-
- Copper-Catalyzed Reductive N-Alkylation of Amides with N-Tosylhydrazones Derived from Ketones
-
A CuI-catalyzed reductive coupling of ketone-derived N-tosylhydrazones with amides is presented. Under the optimized conditions, an array of N-tosylhydrazones derived from aryl–alkyl and diaryl ketones could couple effectively with a wide variety of (hete
- Xu, Peng,Qi, Fu-Ling,Han, Fu-She,Wang, Yan-Hua
-
supporting information
p. 2030 - 2034
(2016/07/28)
-
- Copper-catalyzed radical reaction of N -tosylhydrazones: Stereoselective synthesis of (E)-vinyl sulfones
-
A new chemistry of hydrazines that is a copper-catalyzed radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient one-pot synthesis of alkynes from N-tosylhydrazones has been achieved. The studies provide important complementary approaches for the syntheses of vinyl sulfones and alkynes.
- Mao, Shuai,Gao, Ya-Ru,Zhu, Xue-Qing,Guo, Dong-Dong,Wang, Yong-Qiang
-
supporting information
p. 1692 - 1695
(2015/04/14)
-