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Metal‐Free, Regioselective, Dehydrogenative Cross‐Coupling between Formamides/Aldehydes and Coumarins by C–H Functionalization
Author(s) -
Gupta Mohit,
Kumar Prashant,
Bahadur Vijay,
Kumar Krishan,
Parmar Virinder S.,
Singh Brajendra K.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701764
Subject(s) - regioselectivity , formamides , chemistry , combinatorial chemistry , surface modification , substrate (aquarium) , coupling reaction , organic chemistry , catalysis , oceanography , geology
A highly efficient, single‐step, metal‐free synthetic approach to the synthesis of coumarin‐3‐carboxamides has been developed. The protocol employs tert ‐butyl peroxybenzoate as a radical initiator to achieve the regioselective carboxamidation of coumarins at C‐3 in good‐to‐moderate yields. The established reaction protocol offers a wide substrate scope as it allows the use of both formamides as well as aldehydes as coupling partners with excellent regioselectivity. Furthermore, mechanistic investigations illustrate that the reaction proceeds by a free‐radical pathway.