Transition-Metal-Free Esterification of Amides via Selective N-C Cleavage under Mild Conditions

被引：96

作者：

Li, Guangchen ^{[1
]}

Lei, Peng ^{[1
,2
]}

Szostak, Michal ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem, 73 Warren St, Newark, NJ 07102 USA

[2] China Agr Univ, Coll Sci, Dept Appl Chem, Beijing 100193, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 18期

关键词：

CATALYZED ESTERIFICATION; NICKEL CATALYSIS; TWISTED AMIDES; ARYL ESTERS; DESTABILIZATION; DECARBONYLATION; RELEVANCE; ROTATION;

D O I：

10.1021/acs.orglett.8b02323

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, transition-metal-free, and operationally simple method for esterification of amides by a highly selective cleavage of N-C(O) bonds under exceedingly mild conditions is reported. The reaction is characterized by broad substrate scope and excellent functional group tolerance. The potential of this mild esterification is highlighted by late-stage diversification of natural products and pharmaceuticals. Conceptually, the metal-free acyl functionalization of amides represents a significant step forward as a practical alternative to ligand exchange in acylmetal intermediates.

引用

页码：5622 / 5625

页数：4

共 46 条

[1] Decarbonylative C-H Coupling of Azoles and Aryl Esters: Unprecedented Nickel Catalysis and Application to the Synthesis of Muscoride A [J].

Amaike, Kazuma ;

Muto, Kei ;

Yamaguchi, Junichiro ;

Itami, Kenichiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13573-13576

[2] A New Twist on Amide Solvolysis [J].

Aube, Jeffrey .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (13) :3063-3065

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

Bourne-Branchu, Yann ;

Gosmini, Corinne ;

Danoun, Gregory .

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

[4] Breaking Amides using Nickel Catalysis [J].

Dander, Jacob E. ;

Garg, Neil K. .

ACS CATALYSIS, 2017, 7 (02) :1413-1423

[5] Reliable Determination of Amidicity in Acyclic Amides and Lactams [J].

Glover, Stephen A. ;

Rosser, Adam A. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (13) :5492-5502

[6]

Goossen LJ, 2002, ANGEW CHEM INT EDIT, V41, P1237, DOI 10.1002/1521-3773(20020402)41:7<1237::AID-ANIE1237>3.0.CO

[7]

2-F

[8]

Greenberg A., 2003, The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science

[9] Decarbonylative Cross-Couplings: Nickel Catalyzed Functional Group Interconversion Strategies for the Construction of Complex Organic Molecules [J].

Guo, Lin ;

Rueping, Magnus .

ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (05) :1185-1195

[10] Nickel-Catalyzed Esterification of Aliphatic Amides [J].

Hie, Liana ;

Baker, Emma L. ;

Anthony, Sarah M. ;

Desrosiers, Jean-Nicolas ;

Senanayake, Chris ;

Garg, Neil K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (48) :15129-15132

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