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Regioselective C-H Functionalization of the Six-Membered Ring of the 6,5-Fused Heterocyclic Systems: An Overview

Overview
Journal Molecules
Publisher MDPI
Specialty Biology
Date 2021 Oct 13
PMID 34641306
Citations 2
Authors
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Abstract

The regioselective C-H functionalization of the five-membered ring of the 6,5-fused heterocyclic systems is nowadays well documented due to its high reactivity compared to the six-membered ring. So, developing new procedures of C-H functionalization of the six-membered ring "by thinking out of the box" is extremely challenging, which explains the limited number of reports published to date. This review paper aims to highlight advances achieved in this emerging chemistry research and discusses recently reported methods.

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References
1.
Chen B, Hou X, Li Y, Wu Y . Mechanistic understanding of the unexpected meta selectivity in copper-catalyzed anilide C-H bond arylation. J Am Chem Soc. 2011; 133(20):7668-71. DOI: 10.1021/ja201425e. View

2.
Campeau L, Stuart D, Leclerc J, Bertrand-Laperle M, Villemure E, Sun H . Palladium-catalyzed direct arylation of azine and azole N-oxides: reaction development, scope and applications in synthesis. J Am Chem Soc. 2009; 131(9):3291-306. DOI: 10.1021/ja808332k. View

3.
Ackermann L, Vicente R, Kapdi A . Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. Angew Chem Int Ed Engl. 2009; 48(52):9792-826. DOI: 10.1002/anie.200902996. View

4.
Shi J, Yan Y, Li Q, Xu H, Yi W . Rhodium(III)-catalyzed C2-selective carbenoid functionalization and subsequent C7-alkenylation of indoles. Chem Commun (Camb). 2014; 50(49):6483-6. DOI: 10.1039/c4cc01593b. View

5.
Campeau L, Bertrand-Laperle M, Leclerc J, Villemure E, Gorelsky S, Fagnou K . C2, C5, and C4 azole N-oxide direct arylation including room-temperature reactions. J Am Chem Soc. 2008; 130(11):3276-7. DOI: 10.1021/ja7107068. View