Intramolecular Csp3-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines

被引：14

作者：

Wen, Xiaojin ^{[1
]}

Li, Xinyao ^{[1
]}

Luo, Xiao ^{[1
]}

Wang, Weijin ^{[1
]}

Song, Song ^{[1
,2
]}

Jiao, Ning ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Xue Yuan Rd 38, Beijing 100191, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China

来源：

CHEMICAL SCIENCE | 2020年 / 11卷 / 17期

基金：

中国国家自然科学基金;

关键词：

C-H AMINATION; SCHMIDT REACTION; RING-EXPANSION; CHEMOSELECTIVE AMINATION; EFFICIENT SYNTHESIS; C(SP(3))-H BONDS; HYDROXY AZIDES; ORGANIC AZIDES; NITROGEN; FUNCTIONALIZATION;

D O I：

10.1039/c9sc05522c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular Csp(3)-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp(3)-H and/or C-C bond cleavage. Two C-N single bonds or a C=N double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.

引用

页码：4482 / 4487

页数：6

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