Journal
ACS CATALYSIS
Volume 8, Issue 1, Pages 742-746Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03812
Keywords
benzazepines; benzylamines; C-H activation; Morita-Baylis-Hillman adducts; rhodium
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Funding
- National Research Foundation of Korea (NRF) - Korea government (MSIP) [2016R1A4A1011189, 2016R1C1B2014895, 2017R1A2B2004786]
- Institute for Basic Science [IBS-R010-G1]
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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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