Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes

Krishna N. Tripathi; Avinash H. Bansode; Ravi P. Singh

doi:10.1055/s-0039-1691492

Synthesis, Table of Contents

Synthesis 2020; 52(05): 719-726
DOI: 10.1055/s-0039-1691492

paper

Palladium-Catalyzed Oxidative Annulation of Pyrrolylalkyl-1H-azoles: Towards the Synthesis of Polyheterocyclic Arenes

Krishna N. Tripathi

^aDepartment of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India Email: ravips@chemistry.iitd.ac.in

,

Avinash H. Bansode

^bDivision of Organic Chemistry, National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India

,

Ravi P. Singh∗

^aDepartment of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi 110016, India Email: ravips@chemistry.iitd.ac.in

› Author Affiliations

Abstract

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Abstract

A highly efficient and regioselective palladium-catalyzed annulation protocol for a series of linear and terminally substituted 1,2- and 1,3-di(heteroaryl)alkanes to the corresponding polyheterocyclic arenes is reported. Herein, intramolecular oxidative coupling involving double C(sp²)–H bond functionalization provides a feasible access to biheteroaryl systems annulated to a six-membered ring. The methodology is not restricted to six-membered annulations and was extended to the synthesis of compounds with a seven-membered ring and biheteroaryl core.

Key words

C–H functionalization - pyrroles - oxidative coupling - palladium - imidazoles

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References

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21 CCDC 1918664 (2a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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