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

Abstract

AbstractThe 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 Introduction2 Improved Decarboxylative Arylations3 sp3–sp3 Cross-Coupling of Carboxylic Acids with Aliphatic Bromides4 sp3–sp3 Cross-Coupling of Carboxylic Acids with Aliphatic Alcohols and Amines5 Doubly Decarboxylative sp3–sp3 Cross-Coupling of Carboxylic Acids6 Decarboxylative C–C Bond Formation from (Hetero)aryl Carboxylic Acids7 Conclusions