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

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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.
Publisher
AMER CHEMICAL SOC
Issue Date
2018-01
Language
English
Article Type
Article
Keywords

BAYLIS-HILLMAN ADDUCTS; C-H ACTIVATION; DENSITY FUNCTIONALS; BIOLOGICAL-ACTIVITY; BOND-CLEAVAGE; AZOBENZENES; CYCLIZATION; ALKENYLATION; DERIVATIVES; ALKYLATION

Citation

ACS CATALYSIS, v.8, no.1, pp.742 - 746

ISSN
2155-5435
DOI
10.1021/acscatal.7b03812
URI
http://hdl.handle.net/10203/240159
Appears in Collection
CH-Journal Papers(저널논문)
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