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Decarboxylative Giese‐Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox‐Neutral Protocol
Author(s) -
Ramirez Nieves P.,
GonzalezGomez Jose C.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601478
Subject(s) - chemistry , radical , carboxylic acid , catalysis , photochemistry , organic chemistry , combinatorial chemistry
We describe herein a transition‐metal‐free method for the decarboxylative generation of radicals from carboxylic acids and their 1,4‐addition to Michael acceptors. The Fukuzumi catalyst (9‐mesitylene‐10‐methylacridinium perchlorate, [Acr‐Mes]ClO 4 ) enabled this transformation under visible‐light irradiation at room temperature with CO 2 as the only byproduct. The scope and limitations of this protocol were examined by using a range of Michael acceptors (15 examples) and carboxylic acids (18 examples). The use of 3‐hydroxypivalic acid in this protocol allowed the straightforward formation of a diastereomerically pure δ ‐lactone. Moreover, when a homoallylic acid was used, a radical cascade reaction took place with the formation of three C–C bonds.