Bismuth(V)-Mediated C–H Arylation of Phenols and Naphthols

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

Key words

bismuth - phenols - transmetallation - oxidation - C–H arylation

Publikationsverlauf

Eingereicht: 10. August 2020

Angenommen nach Revision: 18. August 2020

Artikel online veröffentlicht:
28. September 2020

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