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Current Organic Chemistry


ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

Review Article

Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes

Author(s): Fabio Bellina*, Martina La Manna and Elisabetta Rosadoni

Volume 25, Issue 18, 2021

Published on: 08 June, 2021

Page: [2116 - 2141] Pages: 26

DOI: 10.2174/1385272825666210608115144

Price: $65


The functionalization of a Csp2-H bond of an heteroarene with an alkyne represent one of the most attractive procedure for the late-stage functionalization of the aromatic core, due to the structural characteristics and synthetic versatility given by a triple carbon-carbon bond. The aim of this review is to cover the most significant results reported in the literature regarding the synthesis of alkynyl-substituted five-membered heteroarenes by selective direct Csp2-H alkynylation with 1-haloalkynes and analogues, or by cross-dehydrogenative alkynylation (CDA) with terminal alkynes, without making use of directing groups.

Keywords: CH activation, dehydrogenative coupling, inverse Sonogashira coupling, selectivity, heteroarenes, palladium catalyst, azoles.

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