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CC BY-NC-ND 4.0 · Synthesis 2023; 55(20): 3239-3250
DOI: 10.1055/a-2081-1830
DOI: 10.1055/a-2081-1830
short review
Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances
This work was supported by the Engineering and Physical Sciences Research Council (EP/S028595/1 and EP/R020752/1). A.J.C. thanks the Royal Society for a University Research Fellowship (UF150533) and Ph.D. studentship funding (S.L.H), the University of Bath for an URSA Ph.D. studentship (H.E.A.) and a Global Doctoral Scholarship (Q.C), the EPSRC and associated companies for CASE or iCASE Ph.D. studentships (J.C.T.-D. with Syngenta, G.D.J. with AstraZeneca), and AstraZeneca (H.E.A), Janssen (S.L.H), and UCB Biopharma (Q.C.) for generous financial support.
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 - electrochemistryPublication History
Received: 12 March 2023
Accepted after revision: 17 April 2023
Accepted Manuscript online:
26 April 2023
Article published online:
30 May 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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