Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 20, Issue 40, Pages 7923-7928Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ob01360f
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Funding
- Ministerio de Ciencia e Innovacion (MICINN) [CTQ2017-88171-P]
- Generalitat Valenciana [SEJIGENT/2021/005]
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Riboflavin tetraacetate efficiently catalyzes the decarboxylative alkenylation of aryl styryl sulfones, showing excellent stereoselectivity. This metal-free and environmentally friendly method also allows for the regioselective synthesis of internal alkynes.
The decarboxylative alkenylation of aliphatic carboxylic acids with aryl styryl sulfones is efficiently catalyzed by riboflavin tetraacetate under visible light irradiation at room temperature. This metal-free protocol is cost-efficient, environmentally friendly and provides the corresponding olefins with excellent (E)-diastereocontrol. The methodology can also be used to prepare internal alkynes regioselectively by using alkynyl sulfones as radical acceptors. The suitability as building blocks of the olefins obtained was demonstrated by performing an (E)- to (Z) photoisomerization, an iron-catalyzed allylic substitution of the phenoxy group derived from the 2-phenoxycarboxylic acid substrates, as well as syn-epoxidations, and diastereoselective intramolecular iodoarylations. Based on control experiments and DFT calculations, we proposed a reaction mechanism that accounts for the regio- and diastereo-selectivity observed.
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