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

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

Centre for Sustainable Chemical Technologies, Department of Chemistry, University of Bath

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

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 carboncentred 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 (Germany)
Volume	55
Issue number	20
DOIs	https://doi.org/10.1055/a-2081-1830
Publication status	Published - 12 Mar 2023
Externally published	Yes

Keywords

C-C coupling
carboxylic acids
decarboxylative
electrochemistry
photoredox catalysis
radicals

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10.1055/a-2081-1830

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 carboncentred 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.",

keywords = "C-C coupling, carboxylic acids, decarboxylative, electrochemistry, photoredox catalysis, radicals",

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

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month = mar,

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doi = "10.1055/a-2081-1830",

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journal = "Synthesis (Germany)",

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T2 - Recent Advances

AU - Tibbetts, Joshua D.

AU - Askey, Hannah E.

AU - Cao, Qiao

AU - Grayson, James D.

AU - Hobson, Sophie L.

AU - Johnson, George D.

AU - Turner-Dore, Jacob C.

AU - Cresswell, Alexander J.

PY - 2023/3/12

Y1 - 2023/3/12

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 carboncentred 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 carboncentred 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.

KW - C-C coupling

KW - carboxylic acids

KW - decarboxylative

KW - electrochemistry

KW - photoredox catalysis

KW - radicals

UR - https://www.scopus.com/pages/publications/85162786077

U2 - 10.1055/a-2081-1830

DO - 10.1055/a-2081-1830

M3 - Review article

AN - SCOPUS:85162786077

SN - 0039-7881

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EP - 3250

JO - Synthesis (Germany)

JF - Synthesis (Germany)

IS - 20

ER -

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

Abstract

Keywords

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