Ethanol as a Hydrogenating Agent: Palladium-Catalyzed Stereoselective Hydrogenation of Ynamides To Give Enamides

被引：70

作者：

Reddy, Alla Siva ^{[1
]}

Swamy, K. C. Kumara ^{[1
]}

机构：

[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Prades, India

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 24期

关键词：

enamides; ethanol; hydrogenation; palladium; ynamides; SELECTIVE SEMIHYDROGENATION; ALKYNE SEMIHYDROGENATION; FUNCTIONALIZED YNAMIDES; 2+2+2 CYCLOADDITIONS; TANDEM-CYCLIZATION; GOLD CATALYSIS; REDUCTION; ACIDS; HYDROGENOLYSIS; REACTIVITY;

D O I：

10.1002/anie.201702277

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ethanol is shown to act as a hydrogenating agent for ynamides under palladium catalysis. This behavior is different from the normally expected reaction of ethanol addition to alkynes. The reaction shows stereoselectivity for E enamides, which is in contrast to reports using other hydrogenating sources. The method was also extended to ynamines. Alternatively, the use of ethanol and ammonium formate as the hydrogenating source gives Z enamides. The role of ethanol in hydrogenation was demonstrated by means deuterium labeling experiment.

引用

页码：6984 / 6988

页数：5

共 50 条

[41] Enantioselective synthesis of trifluoromethylated dihydroquinoxalinones via palladium-catalyzed hydrogenation [J].

Chen, Mu-Wang ;

Deng, Zhihong ;

Yang, Qin ;

Huang, Jian ;

Peng, Yiyuan .

ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) :746-750

[42] Palladium-Catalyzed Coupling Reactions: Carbonylative Heck Reactions To Give Chalcones [J].

Wu, Xiao-Feng ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5284-5288

[43] Palladium-catalyzed stereoselective intramolecular cyclization and Suzuki coupling of N-arylsulfonyl-α-chloroenamides promoted by a γ-hydroxy group [J].

Yabuuchi, Yuto ;

Sakamoto, Kenta ;

Yoshimura, Tomoyuki ;

Matsuo, Jun-ichi .

TETRAHEDRON, 2018, 74 (30) :4053-4061

[44] Palladium-Catalyzed Stereoselective C-Glycosylation of Glycals with Sodium Arylsulfinates [J].

Ma, Jimei ;

Xiang, Shaohua ;

Jiang, Hong ;

Liu, Xue-Wei .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (05) :949-952

[45] Palladium-catalyzed stereoselective synthesis of multisubstituted allenes and their application in organic transformations [J].

Ogasawara, Masamichi .

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2008, 66 (02) :100-109

[46] Synthesis of chiral trifluoromethylated amines by palladium-catalyzed diastereoselective hydrogenation-hydrogenolysis approach [J].

Török, B ;

Prakash, GKS .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (1-2) :165-168

[47] Covalent Immobilization of Imidazolium Cations Inside a Silica Support: Palladium-Catalyzed Olefin Hydrogenation [J].

Wang, Lei ;

Shylesh, Sankaranarayanapillai ;

Dehe, Daniel ;

Philippi, Thomas ;

Doerr, Gunder ;

Seifert, Andreas ;

Zhou, Zhou ;

Hartmann, Martin ;

Taylor, Robin N. Klupp ;

Jia, Mingjun ;

Ernst, Stefan ;

Thiel, Werner R. .

CHEMCATCHEM, 2012, 4 (03) :395-400

[48] Formation of Ketenimines via the Palladium-Catalyzed Decarboxylative π-Allylic Rearrangement of N-Allot Ynamides [J].

Alexander, Juliana R. ;

Cook, Matthew J. .

ORGANIC LETTERS, 2017, 19 (21) :5822-5825

[49] Palladium-Catalyzed Direct Arylation of Cyclic Enamides with Aryl Silanes by sp2 C-H Activation [J].

Zhou, Hai ;

Xu, Yun-He ;

Chung, Wan-Jun ;

Loh, Teck-Peng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (29) :5355-5357

[50] Palladium-catalyzed asymmetric hydrogenation of simple ketones activated by Bronsted acids [J].

Zhou, Xiao-Yu ;

Wang, Duo-Sheng ;

Bao, Ming ;

Zhou, Yong-Gui .

TETRAHEDRON LETTERS, 2011, 52 (22) :2826-2829

← 1 2 3 4 5 →