Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 15, Pages 2154-2163Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601478
Keywords
Carboxylic acids; Synthetic methods; Radical reactions; Photocatalysis; Sustainable chemistry
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Funding
- Ministerio de Economia y Competitividad [CTQ2015-66624-P]
- University of Alicante [VIGROB-173]
- Institute of Organic Synthesis (ISO)
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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]ClO4) enabled this transformation under visible-light irradiation at room temperature with CO2 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 delta-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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