Regioselective acceptorless dehydrogenative coupling of N-heterocycles toward functionalized quinolines, phenanthrolines, and indoles.

Dinesh Talwar, Angela Gonzalez-de-Castro, Ho Yin Li, Jianliang Xiao
Author Information
  1. Dinesh Talwar: Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD (UK) http://pcwww.liv.ac.uk/∼xiao.

Abstract

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) CH 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.

Keywords

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Created with Highcharts 10.0.0N-heterocyclescouplingdehydrogenativeiridiumCHfunctionalizedfunctionalizationnewstrategydevelopedoxidant-base-freemildconditionsactioncatalystundergomultiplesp3activationstepsgeneratingnucleophilicenaminereactsin situvariouselectrophilesgivehighlyproductscancascadedFriedel-CraftsadditionresultingdoubleRegioselectiveacceptorlesstowardquinolinesphenanthrolinesindolesCCdehydrogenationcomplexes

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