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An Efficient Protocol to Synthesize N‐Acyl‐enamides and ‐Imines by Pd‐Catalyzed Carbonylations
Author(s) -
Wang Lin,
Neumann Helfried,
Spannenberg Anke,
Beller Matthias
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704704
Subject(s) - carbonylation , chemistry , chemoselectivity , catalysis , ligand (biochemistry) , phosphinite , combinatorial chemistry , denticity , medicinal chemistry , amide , reagent , stereochemistry , organic chemistry , receptor , carbon monoxide , crystal structure , biochemistry
For the first time, the bidentate phosphinite ligand 1,2‐bis(di‐ tert ‐butylphosphinoxy)ethane ( t Bu 2 POCH 2 CH 2 OP t Bu 2 ) was synthesized. In the presence of this ligand, various N‐acyl enamides were obtained in good yields and chemoselectivity by Pd‐catalyzed carbonylation reaction of imines containing α‐H. Meanwhile, imines without α‐H could be transformed to N‐acyl imines, which form highly hindered amides by straightforward addition of Grignard reagents.