Copper-assisted Wittig-type olefination of aldehydes with p-toluenesulfonylmethyl isocyanide?
Organic Chemistry Frontiers Pub Date: 2022-06-20 DOI: 10.1039/D2QO00472K
Abstract
The Wittig reaction is a valuable and powerful tool in organic synthesis, providing a convenient route from aldehydes and ketones to alkenes. Herein, a novel copper-assisted Wittig-type olefination of aldehydes with p-toluenesulfonylmethyl isocyanide (TosMIC) is disclosed, providing a direct and operationally simple approach to (E)-vinyl sulfones under mild conditions, compatible with a multitude of common functional groups. Experimental and computational investigations imply that the reaction proceeds through an intriguing electronically-controlled (3 + 2)/retro-(3 + 2) cycloaddition pathway.
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Journal Name：Organic Chemistry Frontiers
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CAS no.: 89640-58-4
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