Transamidation and Decarbonylation of N-Phthaloyl-Amino Acid Amides Enabled by Palladium-Catalyzed Selective C-N Bond Cleavage

被引：5

作者：

Zhang, Hao-Yu ^{[1
]}

Tao, Xuan-Wen ^{[1
]}

Yi, Li-Na ^{[1
]}

Zhao, Zhi-Gang ^{[1
]}

Yang, Qiang ^{[1
]}

机构：

[1] Southwest Minzu Univ, Key Lab Gen Chem, Natl Ethn Affairs Commiss, Coll Chem & Environm, Chengdu 610041, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 01期

基金：

中国国家自然科学基金;

关键词：

H FUNCTIONALIZATION; EFFICIENT SYNTHESIS; SECONDARY AMIDES; PHTHALIMIDES; DERIVATIVES; ACTIVATION; ARYLATION;

D O I：

10.1021/acs.joc.1c02245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amides are important functional synthons that have been widely used in the construction of peptides, natural products, and drugs. The C-N bond cleavage provides the direct method for amide conversion. However, amides, especially secondary amides, tend to be chemically inert due to the resonance of the amide bond. Here, we describe an efficient Pd-catalyzed transamidation and decarbonylation of multiamide structure molecules through C-N bond cleavage with excellent chemoselectivity. The transamidation of secondary amides and the decarbonylation of phthalimide provide meaningful tools for the modification of amino acid derivatives. Moreover, further transformations of azidation and C(sp(3))-H monoarylation emphasized the potential utility of this selective C-N bond cleavage method.

引用

页码：231 / 242

页数：12