TMSCl-Promoted Sulfonylation\nof Propargylic Alcohols\nwith Sodium Sulfinates for the Construction of (<i>E</i>)‑1,3-Disulfonylpropenes and (<i>E</i>)‑1-Sulfonylpropenols

A direct and novel transformation of propargylic alcohols\nwith\nsodium sulfinates for the regio- and stereoselective synthesis of\n(<i>E</i>)-1,3-disulfonylpropenes and (<i>E</i>)-1-sulfonylpropenols was successfully developed in the presence\nof TMSCl under mild conditions. The preliminary mechanistic experiments\ndemonstrated that the reaction underwent an unprecedented dual nucleophilic\nsubstitution/radical addition process, in which sodium sulfinates\nwere used not only as nucleophiles but also as a sulfonyl radical\nsource.

Publication Details

Journal
Figshare
Published
2024-10-12
DOI
https://doi.org/10.1021/acs.joc.4c01829.s001
Primary Topic
Education Methods and Technologies
Type
article
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article

TMSCl-Promoted Sulfonylation\nof Propargylic Alcohols\nwith Sodium Sulfinates for the Construction of (E)‑1,3-Disulfonylpropenes and (E)‑1-Sulfonylpropenols

Figshare
Education Methods and Technologies
article

TMSCl-Promoted Sulfonylation\nof Propargylic Alcohols\nwith Sodium Sulfinates for the Construction of (E)‑1,3-Disulfonylpropenes and (E)‑1-Sulfonylpropenols

article en

Abstract

A direct and novel transformation of propargylic alcohols\nwith\nsodium sulfinates for the regio- and stereoselective synthesis of\n(<i>E</i>)-1,3-disulfonylpropenes and (<i>E</i>)-1-sulfonylpropenols was successfully developed in the presence\nof TMSCl under mild conditions. The preliminary mechanistic experiments\ndemonstrated that the reaction underwent an unprecedented dual nucleophilic\nsubstitution/radical addition process, in which sodium sulfinates\nwere used not only as nucleophiles but also as a sulfonyl radical\nsource.

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Education Methods and Technologies
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TMSCl-Promoted Sulfonylation\nof Propargylic Alcohols\nwith Sodium Sulfinates for the Construction of (<i>E</i>)‑1,3-Disulfonylpropenes and (<i>E</i>)‑1-Sulfonylpropenols · Figshare (2024) | TGRS Research Map | TGRS