Decarboxylative, radical C–C bond formation with alkyl or aryl carboxylic acids: recent advances

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

doi:10.1055/a-2081-1830

Decarboxylative, radical C–C bond formation with alkyl or aryl carboxylic acids: recent advances

Josh Tibbetts^*, Hannah Askey, Qiao Cao, James Grayson, Sophie Hobson, George Johnson, Jacob C. Turner-Dore, Alexander J. Cresswell^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Review article › peer-review

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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.

Original language	English
Pages (from-to)	3239-3250
Number of pages	12
Journal	Synthesis: journal of synthetic organic chemistry
Volume	55
Issue number	20
Early online date	26 Apr 2023
DOIs	https://doi.org/10.1055/a-2081-1830
Publication status	Published - Oct 2023

Bibliographical note

Funding:
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.

Keywords

C-C coupling
carboxylic acids
decarboxylative
electrochemistry
photoredox catalysis
radicals

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Cite this

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title = "Decarboxylative, radical C–C bond formation with alkyl or aryl carboxylic acids: recent advances",

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.",

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author = "Josh Tibbetts and Hannah Askey and Qiao Cao and James Grayson and Sophie Hobson and George Johnson and Turner-Dore, \{Jacob C.\} and Cresswell, \{Alexander J.\}",

note = "Funding: 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.",

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AU - Johnson, George

AU - Turner-Dore, Jacob C.

AU - Cresswell, Alexander J.

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N2 - 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.

AB - 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.

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KW - carboxylic acids

KW - decarboxylative

KW - electrochemistry

KW - photoredox catalysis

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Decarboxylative, radical C–C bond formation with alkyl or aryl carboxylic acids: recent advances

Abstract

Bibliographical note

Keywords

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