Metal-Free-Visible Light C-H Alkylation of Heteroaromatics via Hypervalent Iodine-Promoted Decarboxylation

Organic Letters
Julien GenovinoMathieu Frenette

Abstract

A metal-free photoredox C-H alkylation of heteroaromatics from readily available carboxylic acids using an organic photocatalyst and hypervalent iodine reagents under blue LED light is reported. The developed methodology tolerates a broad range of functional groups and can be applied to the late-stage functionalization of drugs and drug-like molecules. The reaction mechanism was investigated with control experiments and photophysical experiments as well as DFT calculations.

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Citations

Oct 20, 2018·Organic & Biomolecular Chemistry·Atul Kumar Chaturvedi, Namrata Rastogi
Dec 14, 2018·Chemical Communications : Chem Comm·Ashique Hussain JatoiYannick Landais
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen
May 9, 2019·Organic & Biomolecular Chemistry·Yating Zhao, Wujiong Xia
May 23, 2019·Organic & Biomolecular Chemistry·Mustafa Uygur, Olga García Mancheño
Jun 20, 2019·Organic & Biomolecular Chemistry·Rajnish BudhwanSandip Murarka
Mar 20, 2019·Angewandte Chemie·Rupert S J Proctor, Robert J Phipps
Feb 7, 2020·Angewandte Chemie·Masaya NakajimaTetsuhiro Nemoto

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