Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp2)-H Functionalization

被引：40

作者：

Pandey, Ashok Kumar ^{[1
]}

Han, Sang Hoon ^{[1
]}

Mishra, Neeraj Kumar ^{[1
]}

Kang, Dahye ^{[2
,3
]}

Lee, Suk Hun ^{[1
]}

Chun, Rina ^{[1
]}

Hong, Sungwoo ^{[2
,3
]}

Park, Jung Su ^{[4
]}

Kim, In Su ^{[1
]}

机构：

[1] Sungkyunkwan Univ, Sch Pharm, Suwon 16419, South Korea

[2] Inst for Basic Sci Korea, Ctr Catalyt Hydrocarbon Functionalizat, Daejeon 34141, South Korea

[3] Korea Adv Inst Sci & Technol, Dept Chem, Daejeon 34141, South Korea

[4] Sookmyung Womens Univ, Dept Chem, Seoul 04310, South Korea

来源：

ACS CATALYSIS | 2018年 / 8卷 / 01期

基金：

新加坡国家研究基金会;

关键词：

benzazepines; benzylamines; C-H activation; Morita-Baylis-Hillman adducts; rhodium; BAYLIS-HILLMAN REACTION; C-H ALKYLATION; DENSITY FUNCTIONALS; AZOBENZENES; CYCLIZATION; ALKENYLATION; DERIVATIVES; ALLYLATION; ACTIVATION; DISCOVERY;

D O I：

10.1021/acscatal.7b03812

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The rhodium(III)-catalyzed cross-coupling reaction between commercially available benzylamines and Morita-Baylis--Hillman (MBH) adducts is described. This protocol provides a facile access to various 2-benzazepine derivatives via the C(sp(2))-H activation of N-allylated benzylamines and subsequent intramolecular olefin insertion followed by N-allylation reaction. A range of substrates has been used, and a high level of chemoselectivity as well as functional group tolerance was observed. To gain mechanistic insight of this transformation, DFT performed. calculations were also performed.

引用

页码：742 / 746

页数：5

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