Decarboxylative, Radical C–C Bond Formation with Alkyl or Aryl Carboxylic Acids: Recent Advances
Joshua D. Tibbetts, Alexander J. Cresswell, Hannah E. Askey, Qiao Cao, James D. Grayson, Sophie L. Hobson, G. Dana Johnson, Jacob C. Turner-Dore
Abstract
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