Abstract
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.
Current Organic Chemistry
Title:Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes
Volume: 25 Issue: 18
Author(s): Fabio Bellina*, Martina La Manna and Elisabetta Rosadoni
Affiliation:
- Dipartimento di Chimica e Chimica Industriale, Universita di Pisa, Pisa,Italy
Keywords: CH activation, dehydrogenative coupling, inverse Sonogashira coupling, selectivity, heteroarenes, palladium catalyst, azoles.
Abstract: 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.
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Cite this article as:
Bellina Fabio*, La Manna Martina and Rosadoni Elisabetta , Undirected, Selective Csp2-H Alkynylation of Five-membered Heteroarenes, Current Organic Chemistry 2021; 25 (18) . https://dx.doi.org/10.2174/1385272825666210608115144
DOI https://dx.doi.org/10.2174/1385272825666210608115144 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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