A Sulfur Monoxide Surrogate Designed for the Synthesis of Sulfoxides and Sulfinamides

05 October 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Sulfur monoxide (SO) is a highly reactive species that cannot be isolated in bulk. However, SO can play a pivotal role as a fundamental building block in organic synthesis. Reported herein is the design and application of a sulfinylhydrazine reagent as an easily prepared sulfur monoxide surrogate. We show facile thermal SO transfer from this reagent to dienes where a reaction using a mechanistic probe suggests the generation of singlet SO. Combined with Grignard reagents and appropriate carbon or nitrogen electrophiles, the reagent serves as an effective “SO” donor to enable the one-pot, three-component synthesis of sulfoxides and sulfinamides.

Supplementary materials

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Supporting Information
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Experimental procedures, Characterization data, Spectra
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