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Synlett 2021; 32(03): 235-240
DOI: 10.1055/s-0040-1706294
DOI: 10.1055/s-0040-1706294
synpacts
Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols
This work was supported by the Engineering and Physical Sciences Research Council (EPSRC) Centre for Doctoral Training in Sustainable Chemistry (Grant number EP/ S022236/1) through a PhD studentship to A.S.
This paper is dedicated to Dr Mark Jurrat in celebration of the birth of his daughter, Merle Olivia
Abstract
We recently reported a general and practical strategy for the Bi(V)-mediated C–H arylation of phenols and naphthols. Our telescoped protocol proceeds via transmetallation from readily available arylboronic acids to a stable Bi(III) precursor, oxidation to a reactive Bi(V) intermediate, and subsequent ortho-selective phenol arylation. The process exhibits broad scope with respect to both components and tolerates functionality that is incompatible with conventional cross-coupling methods. Preliminary investigations provide insight into the mechanism of each key reaction step.
1 Introduction
2 Design of a Modular and Practical Arylating System
3 B-to-Bi Transmetallation: Scope and Mechanism
4 Oxidative C–H Arylation: Exemplification and Mechanism
5 Conclusionsions
Publication History
Received: 10 August 2020
Accepted after revision: 18 August 2020
Article published online:
28 September 2020
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