Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light
Rajdip Chowdhury, Zhunzhun Yu, My Linh Tong, Stefanie V. Kohlhepp, Xiang Yin, Abraham Mendoza
Abstract
Photoexcited dihydronicotinamides like NADH and analogues have been found to generate alkyl radicals upon reductive decarboxylation of redox-active esters without auxiliary photocatalysts. This principle allowed aliphatic photocoupling between redox-active carboxylate derivatives and electron-poor olefins, displaying surprising water and air-tolerance and unusually high coupling rates in dilute conditions. The orthogonality of the reaction in the presence of other carboxylic acids and its utility in the functionalization of DNA is presented, notably using visible light in combination with NADH, the ubiquitous reductant of life.
Topics & Concepts
ChemistryDecarboxylationAlkylRedoxPhotochemistryCarboxylateRadicalVisible spectrumCoupling (piping)Coupling reactionCombinatorial chemistryOrganic chemistryCatalysisEngineeringOptoelectronicsPhysicsMechanical engineeringRadical Photochemical ReactionsPhotochromic and Fluorescence ChemistrySynthesis of Indole Derivatives