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Copper(I)-Catalyzed Nucleophilic Addition of Ynamides to Acyl Chlorides and Activated N-Heterocycles

Author:
Zhang, Peng, Cook, Andrea M., Liu, Yang, Wolf, Christian
Source:
Journal of organic chemistry 2014 v.79 no.9 pp. 4167-4173
ISSN:
1520-6904
Subject:
Lewis bases, ambient temperature, catalysts, chemical bonding, chemical reactions, chemical structure, chlorides, copper, iodides, organic chemistry, pyridines, quinolines, regioselectivity
Abstract:
The addition of ynamides to acyl chlorides and N-heterocycles activated in situ with ethyl chloroformate has been accomplished at room temperature using copper iodide as catalyst. This economical and practical carbon–carbon bond formation provides convenient access to a variety of 3-aminoynones from aliphatic and aromatic acyl chlorides in up to 99% yield. The addition to pyridines and quinolines occurs under almost identical conditions and proceeds with good to high regioselectivity, producing the corresponding 1,2-dihydro-N-heterocycles in up to 95% yield.
Agid:
5503460