Decarboxylative Giese‐Type Reaction of Carboxylic Acids Promoted by Visible Light: A Sustainable and Photoredox‐Neutral Protocol | Zendy

Ramirez Nieves P. | Zendy; GonzalezGomez Jose C. | Zendy

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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.

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