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Visible‐Light‐Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
Author(s) -
Patra Tuhin,
Mukherjee Satobhisha,
Ma Jiajia,
StriethKalthoff Felix,
Glorius Frank
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201904671
Subject(s) - decarboxylation , homolysis , chemistry , aryl , alkyl , photochemistry , radical , aryl radical , heteroatom , organic chemistry , catalysis
Abstract Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond‐forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single‐electron‐transfer mechanism and “switch on” an energy‐transfer‐mediated homolysis of unsymmetrical σ‐bonds for a concerted fragmentation/decarboxylation process.