Regioselective Acceptorless Dehydrogenative Coupling of N‐Heterocycles toward Functionalized Quinolines, Phenanthrolines, and Indoles | Zendy

Talwar Dinesh | Zendy; GonzalezdeCastro Angela | Zendy; Li Ho Yin | Zendy; Xiao Jianliang | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201500346

Subject(s) - regioselectivity , chemistry , electrophile , iridium , combinatorial chemistry , enamine , catalysis , nucleophile , surface modification , indole test , coupling (piping) , 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.

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