Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances

Joshua D. Tibbetts; Hannah E. Askey; Qiao Cao; James D. Grayson; Sophie L. Hobson; George D. Johnson; Jacob C. Turner-Dore; Alexander J. Cresswell

doi:10.1055/a-2081-1830

Synthesis, Table of Contents

CC BY-NC-ND 4.0 · Synthesis 2023; 55(20): 3239-3250
DOI: 10.1055/a-2081-1830

short review

Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances

Joshua D. Tibbetts∗

,

Hannah E. Askey

,

Qiao Cao

,

James D. Grayson

,

Sophie L. Hobson

,

George D. Johnson

,

Jacob C. Turner-Dore

,

Alexander J. Cresswell ∗

Abstract

All articles of this category

Dedicated to the memory of Professor John Fossey

Abstract

The ubiquity of carboxylic acids as naturally derived or man-made chemical feedstocks has spurred the development of powerful, decarboxylative C–C bond-forming transformations for organic synthesis. Carboxylic acids benefit not only from extensive commercial availability, but are stable surrogates for organohalides or organometallic reagents in transition-metal-catalysed cross-coupling. Open shell reactivity of carboxylic acids (or derivatives thereof) to furnish carbon-centred radicals is proving transformative for synthetic chemistry, enabling novel and strategy-level C(sp³)–C bond disconnections with exquisite chemoselectivity. This short review will summarise several of the latest advances in this ever-expanding area.

1 Introduction

2 Improved Decarboxylative Arylations

3 sp³–sp³ Cross-Coupling of Carboxylic Acids with Aliphatic Bromides

4 sp³–sp³ Cross-Coupling of Carboxylic Acids with Aliphatic Alcohols and Amines

5 Doubly Decarboxylative sp³–sp³ Cross-Coupling of Carboxylic Acids

6 Decarboxylative C–C Bond Formation from (Hetero)aryl Carboxylic Acids

7 Conclusions

Key words

decarboxylative - C–C coupling - radicals - carboxylic acids - photoredox catalysis - electrochemistry

Full Text

References

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