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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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