Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light | Zendy

Rajdip Chowdhury | Zendy; Zhunzhun Yu | Zendy; My Linh Tong | Zendy; Stefanie V. Kohlhepp | Zendy; Xiang Yin | Zendy; Abraham Mendoza | Zendy

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Decarboxylative Alkyl Coupling Promoted by NADH and Blue Light

Author(s) -

Rajdip Chowdhury,

Zhunzhun Yu,

My Linh Tong,

Stefanie V. Kohlhepp,

Xiang Yin,

Abraham Mendoza

Publication year - 2020

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.0c09678

Subject(s) - chemistry , decarboxylation , alkyl , redox , photochemistry , carboxylate , radical , visible spectrum , coupling (piping) , coupling reaction , combinatorial chemistry , organic chemistry , catalysis , mechanical engineering , physics , optoelectronics , engineering

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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