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Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions.

Authors :
Patra T
Mukherjee S
Ma J
Strieth-Kalthoff F
Glorius F
Source :
Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Jul 29; Vol. 58 (31), pp. 10514-10520. Date of Electronic Publication: 2019 Jul 03.
Publication Year :
2019

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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Details

Language :
English
ISSN :
1521-3773
Volume :
58
Issue :
31
Database :
MEDLINE
Journal :
Angewandte Chemie (International ed. in English)
Publication Type :
Academic Journal
Accession number :
31162874
Full Text :
https://doi.org/10.1002/anie.201904671