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

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Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp2)–H Functionalization
ACS Catalysis ( IF 11.3 ) Pub Date : 2017-12-26 00:00:00 , DOI: 10.1021/acscatal.7b03812
Ashok Kumar Pandey ₁ , Sang Hoon Han ₁ , Neeraj Kumar Mishra ₁ , Dahye Kang _{2,

3} , Suk Hun Lee ₁ , Rina Chun ₁ , Sungwoo Hong _{2,

3} , Jung Su Park ₄ , In Su Kim ₁

Affiliation

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(sp²)–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 calculations were also performed.

中文翻译：

在铑（III）催化下，通过C（sp ²）–H官能化由苄胺和MBH加合物合成2-苯并ze庚因

描述了铑（III）催化的市售苄胺与森田-贝利斯-希尔曼（MBH）加合物之间的交叉偶联反应。该方案通过N-烯丙基化的苄胺的C（sp ²）-H活化和随后的分子内烯烃插入以及N-烯丙基化反应，提供了对各种2-苯并ze庚因衍生物的便捷访问。已经使用了多种底物，并且观察到高水平的化学选择性以及官能团耐受性。为了获得这种转换的机械原理，还进行了DFT计算。

更新日期：2017-12-26

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