Molecular Iodine Mediated Oxidation of Arylated α‐Carbonyl Sulfoxonium Ylides to 1,2‐Dicarbonyl‐Containing Compounds.

Autor:	Echemendía, Radell, De Jesus, Matheus P., Furniel, Lucas G., Day, David Philip, Burtoloso, Antonio C. B.
Předmět:	YLIDES IODINE ETHYL acetate ORGANIC synthesis OXIDATION ALCOHOL oxidation DIMETHYL sulfoxide
Zdroj:	European Journal of Organic Chemistry; 7/14/2022, Vol. 2022 Issue 26, p1-7, 7p
Abstrakt:	Sulfoxonium ylides in recent years have proved to be versatile building blocks and have found applications in the synthesis of structurally diverse organic molecules. In this work, we report a new oxidative, molecular iodine‐mediated transformation on sterically encumbered arylated sulfoxonium ylides, which give access to 1,2‐dicarbonyl containing compounds. Twenty‐six examples have been realized (47–92 % yields), with structural diversity modified at two key sites on the sulfoxonium ylide reactants. Furthermore, the protocol benefits from the use of inexpensive molecular iodine to mediate the oxidation and, from a sustainability viewpoint, short reaction times (30 minutes), ambient temperature, and ethyl acetate as a greener reaction solvent. Experimental studies also gave insight to the mechanism of the reaction, involving DMSO as an oxygen source. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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