Recent Progress on Transition-Metal-Mediated Reductive C(sp³)–O Bond Radical Addition and Coupling Reactions

Abstract

In this short review, we summarize the recent developments on thermo-driven C(sp³)–O bond radical scission methods and their applications in the construction of C(sp³)–C bonds via conjugate addition with activated double bonds and reductive coupling mediated by economic 3d metals, in particular nickel. We have arranged the review based on three approaches for C(sp³)–O bond radical scission (vide infra). After generating the radical intermediates, their subsequent transformation into C(sp³)–C bonds enabled by C(sp³)–O cross-electrophile coupling with carbon electrophiles is discussed in detail.

1 Introduction

2 Direct Single-Electron Transfer to a C(sp³)–O Bond

3 Radical Scission of Activated C(sp³)–O Bonds via Single-Electron Transfer to Protecting Groups

4 In Situ Activation of Alcohols

5 Summary and Outlook

Key words

alcohols - C–O bonds - radicals - C–C bonds - reductive

Publication History

Received: 31 March 2022

Accepted after revision: 10 May 2022

Accepted Manuscript online:
10 May 2022

Article published online:
30 June 2022

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