Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids
Naoki Oku, Masahiro Murakami, Tomoya Miura
Abstract
A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.
Topics & Concepts
ChemistryBorylationIndole testCatalysisCoupling reactionIridiumDerivative (finance)PalladiumCombinatorial chemistryReaction conditionsMedicinal chemistryOrganic chemistryArylFinancial economicsEconomicsAlkylRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry