Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp(2))-H Functionalization
- Authors
- Pandey, Ashok Kumar; Han, Sang Hoon; Mishra, Neeraj Kumar; Kang, Dahye; Lee, Suk Hun; Chun, Rina; Hong, Sungwoo; Park, Jung Su; Kim, In Su
- Issue Date
- Jan-2018
- Publisher
- AMER CHEMICAL SOC
- Keywords
- benzazepines; benzylamines; C-H activation; Morita-Baylis-Hillman adducts; rhodium
- Citation
- ACS CATALYSIS, v.8, no.1, pp 742 - 746
- Pages
- 5
- Journal Title
- ACS CATALYSIS
- Volume
- 8
- Number
- 1
- Start Page
- 742
- End Page
- 746
- URI
- https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/4766
- DOI
- 10.1021/acscatal.7b03812
- ISSN
- 2155-5435
- Abstract
- 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.
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