A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides

[Image: see text] A new N-silyl sulfinylamine reagent allows the rapid preparation of a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides, using Grignard, organolithium, or organozinc reagents to introduce the carbon fragment. Treatment of these primary sulfinamides with an amine...

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Autores principales: Ding, Mingyan, Zhang, Ze-Xin, Davies, Thomas Q., Willis, Michael C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084605/
https://www.ncbi.nlm.nih.gov/pubmed/35188396
http://dx.doi.org/10.1021/acs.orglett.2c00347
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author Ding, Mingyan
Zhang, Ze-Xin
Davies, Thomas Q.
Willis, Michael C.
author_facet Ding, Mingyan
Zhang, Ze-Xin
Davies, Thomas Q.
Willis, Michael C.
author_sort Ding, Mingyan
collection PubMed
description [Image: see text] A new N-silyl sulfinylamine reagent allows the rapid preparation of a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides, using Grignard, organolithium, or organozinc reagents to introduce the carbon fragment. Treatment of these primary sulfinamides with an amine in the presence of a hypervalent iodine reagent leads directly to NH-sulfonimidamides. This two-step sequence is straightforward to perform and provides a modular approach to sulfonimidamides, allowing ready variation of both reaction components, including primary and secondary amines.
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spelling pubmed-90846052022-05-10 A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides Ding, Mingyan Zhang, Ze-Xin Davies, Thomas Q. Willis, Michael C. Org Lett [Image: see text] A new N-silyl sulfinylamine reagent allows the rapid preparation of a broad range of (hetero)aryl, alkenyl, and alkyl primary sulfinamides, using Grignard, organolithium, or organozinc reagents to introduce the carbon fragment. Treatment of these primary sulfinamides with an amine in the presence of a hypervalent iodine reagent leads directly to NH-sulfonimidamides. This two-step sequence is straightforward to perform and provides a modular approach to sulfonimidamides, allowing ready variation of both reaction components, including primary and secondary amines. American Chemical Society 2022-02-21 2022-03-04 /pmc/articles/PMC9084605/ /pubmed/35188396 http://dx.doi.org/10.1021/acs.orglett.2c00347 Text en © 2022 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ding, Mingyan
Zhang, Ze-Xin
Davies, Thomas Q.
Willis, Michael C.
A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title_full A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title_fullStr A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title_full_unstemmed A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title_short A Silyl Sulfinylamine Reagent Enables the Modular Synthesis of Sulfonimidamides via Primary Sulfinamides
title_sort silyl sulfinylamine reagent enables the modular synthesis of sulfonimidamides via primary sulfinamides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9084605/
https://www.ncbi.nlm.nih.gov/pubmed/35188396
http://dx.doi.org/10.1021/acs.orglett.2c00347
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