Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Oct 30

PMID 33125842

Citations 13

Authors

Rajdip Chowdhury

Zhunzhun Yu

My Linh Tong

Stefanie V Kohlhepp

Xiang Yin

Abraham Mendoza

Affiliations

Soon will be listed here.

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.

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