- Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
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Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
- Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
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- A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
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The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
- Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
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supporting information
p. 4078 - 4084
(2019/10/28)
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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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p. 1820 - 1824
(2019/09/09)
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- Cross-Dehydrogenating Coupling of Aldehydes with Amines/R-OTBS Ethers by Visible-Light Photoredox Catalysis: Synthesis of Amides, Esters, and Ureas
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A straightforward synthesis of amides, ureas, and esters is reported by visible-light cross-dehydrogenating coupling (CDC) of aldehydes (or amine carbaldehydes) and amines/R-OTBS ethers by photoredox catalysis. The reaction is found to be general and high yielding. A plausible mechanistic pathway has been proposed for these transformations and is supported by appropriate controlled experiments.
- Pandey, Ganesh,Koley, Suvajit,Talukdar, Ranadeep,Sahani, Pramod Kumar
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supporting information
p. 5861 - 5865
(2018/09/21)
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- Synthesis of Hydroxybenzoic Acids and Their Esters by Reaction of Phenols with Carbon Tetrachloride and Alcohols in the Presence of Iron Catalysts
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Alkyl esters of hydroxy-, methoxy-, and ethoxybenzoic and cresotic acids have been synthesized by reaction of phenols, anisole, phenetole, and cresols with carbon tetrachloride and alcohols in the presence of iron catalysts.
- Bayguzina,Tarisova,Khusnutdinov
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p. 208 - 215
(2018/03/26)
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- Aminocarbonylation of Aryl Tosylates to Carboxamides
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The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.
- Chung, Seungwon,Sach, Neal,Choi, Chulho,Yang, Xiaojing,Drozda, Susan E.,Singer, Robert A.,Wright, Stephen W.
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supporting information
p. 2848 - 2851
(2015/06/16)
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- Manganese(II)-Catalyzed Esterification of N-β-Hydroxyethylamides
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A catalyst system of manganese with 2,2-bipyridine for amide alcoholysis of N-β-hydroxyethylamides is described. This protocol enabled selective cleavage of the amide bond through a mechanism involving sequential N,O-acyl rearrangement and transesterification.
- Nishii, Yuji,Akiyama, Shoko,Kita, Yusuke,Mashima, Kazushi
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supporting information
p. 1831 - 1834
(2015/08/06)
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- Combined catalytic system of scandium triflate and boronic ester for amide bond cleavage
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We have found that the combination of scandium with boronic ester enables the cleavage of amide bonds. Primary amides were converted to the corresponding esters in the presence of catalytic amounts of scandium triflate and boronic ester under mild and neutral conditions. This unique catalytic system can be applied to the deprotection of acetylaniline derivatives. In addition, control NMR experiments were carried out to examine the effect of the boronic esters. Copyright
- Kita, Yusuke,Nishii, Yuji,Onoue, Akihiro,Mashima, Kazushi
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supporting information
p. 3391 - 3395
(2013/12/04)
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- Synthesis of tert-butyl peroxyacetals from benzyl, allyl, or propargyl ethers via iron-promoted C-H bond functionalization
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When benzyl, allyl, and propargyl ethers were treated with tert-butyl hydroperoxide and a catalytic amount of iron(III) acetylacetonate, tert-butyl peroxyacetals were produced in good to excellent yields, via C-H bond functionalization. This method is also applicable to ethylene acetals of unsaturated aldehydes to give peroxyorthoesters.
- Iwata, Satoshi,Hata, Takeshi,Urabe, Hirokazu
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supporting information
p. 3480 - 3484
(2013/02/22)
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- Zinc-catalyzed amide cleavage and esterification of β- hydroxyethylamides
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Snipping tool: Zn(OTf)2 is an efficient catalyst for selective cleavage of amides bearing a β-hydroxyethyl group on the nitrogen atom. The mechanism involves an N,O-acyl rearrangement and transesterification. This new catalytic system can be applied to sequence-specific peptide bond scission at the amine side of a serine residue. Tf=trifluoromethanesulfonyl. Copyright
- Kita, Yusuke,Nishii, Yuji,Higuchi, Takafumi,Mashima, Kazushi
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supporting information; experimental part
p. 5723 - 5726
(2012/08/07)
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- Development of new palladium catalysts for the alkoxycarbonylation of aryl chlorides
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The alkoxycarbonylation of different aryl chlorides was studied. Studies of the butoxycarbonylation of 4-chlorobenzotrifluoride and chlorobenzene using chelating ferrocenylphosphines reveal the advantages of these ligands compared to the well-known tricyc
- M?gerlein, Wolfgang,Indolese, Adriano F,Beller, Matthias
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- A more efficient catalyst for the carbonylation of chloroarenes
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The right ligand enables the efficient carbonylation of unactivated chloroarenes. A general synthesis of benzoic acid derivatives is possible with the palladium - Ferrocenylphosphane catalysts (see scheme).
- Maegerlein, Wolfgang,Indolese, Adriano F.,Beller, Matthias
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p. 2856 - 2859
(2007/10/03)
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- Advances in the carbonylation of aryl halides using palladium catalysts
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The palladium-catalyzed carbonylation of aryl halides is shown to be a versatile tool for the synthesis of various benzoic and heteroaromatic acid derivatives. Recent developments from our laboratories in this area are presented.
- Beller, Matthias,Indolese, Adriano F.
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p. 684 - 687
(2007/10/03)
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- REARRANGEMENT OF SUBSTITUTED AROMATIC ACETALS CATALYSED BY γ-ALUMINA
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Aromatic acetals over γ-alumina undergo rearrangement to give the corresponding esters (b) and ethers (c) in good yield.The product distribution varied unusually over the range of reaction temperatures.The effect of substituents has also been felt much in the study.Probable mechanisms have been suggested for the reaction.The catalyst has been characterized by various studies and the specific poisoning of the catalyst has been done with NH3, CO2 and H2S.
- Xavier, N.,Arulraj, S. J.
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p. 2875 - 2878
(2007/10/02)
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- PALLADIUM(0) AND RHODIUM(I) CATALYSIS OF THE CARBONYLATION OF UNACTIVATED BROMIDES
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Alkyl, vinyl, and aromatic bromides react with organoborates and carbon monoxide, in the presence of catalytic quantities of 1,5-hexadienerhodium(I) chloride dimer and tetrakis(triphenylphosphine)palladium(0), to give carboxylic esters in good yields.
- Hashem, Khaled E.,Woell, James B.,Alper, Howard
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p. 4879 - 4880
(2007/10/02)
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