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Regioselective Acceptorless Dehydrogenative Coupling of N‐Heterocycles toward Functionalized Quinolines, Phenanthrolines, and Indoles
Author(s) -
Talwar Dinesh,
GonzalezdeCastro Angela,
Li Ho Yin,
Xiao Jianliang
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201500346
Subject(s) - regioselectivity , electrophile , chemistry , iridium , enamine , combinatorial chemistry , catalysis , nucleophile , coupling (piping) , surface modification , organic chemistry , materials science , metallurgy
A new strategy has been developed for the oxidant‐ and base‐free dehydrogenative coupling of N‐heterocycles at mild conditions. Under the action of an iridium catalyst, N‐heterocycles undergo multiple sp 3 CH activation steps, generating a nucleophilic enamine that reacts in situ with various electrophiles to give highly functionalized products. The dehydrogenative coupling can be cascaded with Friedel–Crafts addition, resulting in a double functionalization of the N‐heterocycles.