NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds

被引：8

作者：

Zhang, Yuqi ^{[1
]}

Ye, Xiaojing ^{[1
]}

Liu, Sicheng ^{[1
]}

Chen, Wei ^{[1
]}

Majeed, Irfan ^{[1
]}

Liu, Tingting ^{[1
]}

Zhu, Yulin ^{[1
]}

Zeng, Zhuo ^{[1
,2
]}

机构：

[1] South China Normal Univ, Coll Chem & Environm, Guangzhou 510006, Peoples R China

[2] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, Shanghai, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2021年 / 19卷 / 39期

基金：

中国国家自然科学基金;

关键词：

NICKEL-CATALYZED ACTIVATION; FREE TRANSAMIDATION; SECONDARY AMIDES; THIOESTERIFICATION; ESTERIFICATION; CARBOXAMIDES; ACCESS; ESTERS;

D O I：

10.1039/d1ob01409a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.

引用

页码：8566 / 8571

页数：6

共 56 条

[1] Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst [J].

Allen, C. Liana ;

Atkinson, Benjamin N. ;

Williams, Jonathan M. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) :1383-1386

[2] A two-step approach to achieve secondary amide transamidation enabled by nickel catalysis [J].

Baker, Emma L. ;

Yamano, Michael M. ;

Zhou, Yujing ;

Anthony, Sarah M. ;

Garg, Neil K. .

NATURE COMMUNICATIONS, 2016, 7

[3] Transamidation of Carboxamides Catalyzed by Fe(III) and Water [J].

Becerra-Figueroa, Liliana ;

Ojeda-Porras, Andrea ;

Gamba-Sanchez, Diego .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10) :4544-4552

[4] Cobalt-Catalyzed Esterification of Amides [J].

Bourne-Branchu, Yann ;

Gosmini, Corinne ;

Danoun, Gregory .

CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (42) :10043-10047

[5] Analysis of Past and Present Synthetic Methodologies on Medicinal Chemistry: Where Have All the New Reactions Gone? [J].

Brow, Dean G. ;

Bostrom, Jonas .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (10) :4443-4458

[6] Palladium-Catalyzed Arylation of Fluoroalkylamines [J].

Brusoe, Andrew T. ;

Hartwig, John F. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (26) :8460-8468

[7] Rigid-rod polymeric fibers [J].

Chae, HG ;

Kumar, S .

JOURNAL OF APPLIED POLYMER SCIENCE, 2006, 100 (01) :791-802

[8] Chemoselective direct reductive trifluoromethylation of amides: a flexible access to functionalized α-trifluoromethylamines [J].

Chen, Hang ;

Ye, Jian-Liang ;

Huang, Pei-Qiang .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (06) :943-947

[9] N-Acylsuccinimides: Efficient acylative coupling reagents in palladium-catalyzed Suzuki coupling via C-N cleavage [J].

Cui, Ming ;

Chen, Zeyu ;

Liu, Tingting ;

Wang, Hui ;

Zeng, Zhuo .

TETRAHEDRON LETTERS, 2017, 58 (40) :3819-3822

[10] Palladium-catalyzed Sonogashira coupling of amides: access to ynones via C-N bond cleavage [J].

Cui, Ming ;

Wu, Hongxiang ;

Jian, Junsheng ;

Wang, Hui ;

Liu, Chao ;

Daniel, Stelck ;

Zeng, Zhuo .

CHEMICAL COMMUNICATIONS, 2016, 52 (81) :12076-12079

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