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

Li Cheng; Quan Lin; Yunrong Chen; Hegui Gong

doi:10.1055/a-1848-3005

Synthesis, Table of Contents

Synthesis 2022; 54(20): 4426-4446
DOI: 10.1055/a-1848-3005

short review

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

Authors

Li Cheng

^aSchool of Materials Science and Engineering, Shanghai University, Shanghai 200444, P. R. of China
Quan Lin

^aSchool of Materials Science and Engineering, Shanghai University, Shanghai 200444, P. R. of China
Yunrong Chen∗

^bCenter for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China
Hegui Gong ∗

^bCenter for Supramolecular Chemistry and Catalysis and Department of Chemistry, Shanghai University, Shanghai 200444, P. R. of China

Abstract

All articles of this category

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

Full Text

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