Cargando…

Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines

[Image: see text] We report the synthesis of sulfinamides using organometallic reagents, a sulfur dioxide reagent, and nitrogen based-nucleophiles. The addition of an organometallic reagent to the commercially available sulfur dioxide surrogate, DABSO, generates a metal sulfinate which is reacted wi...

Descripción completa

Detalles Bibliográficos
Autores principales: Lo, Pui Kin Tony, Oliver, Gwyndaf A., Willis, Michael C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304903/
https://www.ncbi.nlm.nih.gov/pubmed/32286844
http://dx.doi.org/10.1021/acs.joc.0c00334
_version_ 1783548352086933504
author Lo, Pui Kin Tony
Oliver, Gwyndaf A.
Willis, Michael C.
author_facet Lo, Pui Kin Tony
Oliver, Gwyndaf A.
Willis, Michael C.
author_sort Lo, Pui Kin Tony
collection PubMed
description [Image: see text] We report the synthesis of sulfinamides using organometallic reagents, a sulfur dioxide reagent, and nitrogen based-nucleophiles. The addition of an organometallic reagent to the commercially available sulfur dioxide surrogate, DABSO, generates a metal sulfinate which is reacted with thionyl chloride to form a sulfinyl chloride intermediate. Trapping the sulfinyl chlorides in situ with a variety of nitrogen nucleophiles delivers sulfinamides in 32–83% yields. Each stage of the process is performed at room temperature, and the total reaction time is only 1.5 h.
format Online
Article
Text
id pubmed-7304903
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-73049032020-06-22 Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines Lo, Pui Kin Tony Oliver, Gwyndaf A. Willis, Michael C. J Org Chem [Image: see text] We report the synthesis of sulfinamides using organometallic reagents, a sulfur dioxide reagent, and nitrogen based-nucleophiles. The addition of an organometallic reagent to the commercially available sulfur dioxide surrogate, DABSO, generates a metal sulfinate which is reacted with thionyl chloride to form a sulfinyl chloride intermediate. Trapping the sulfinyl chlorides in situ with a variety of nitrogen nucleophiles delivers sulfinamides in 32–83% yields. Each stage of the process is performed at room temperature, and the total reaction time is only 1.5 h. American Chemical Society 2020-04-14 2020-05-01 /pmc/articles/PMC7304903/ /pubmed/32286844 http://dx.doi.org/10.1021/acs.joc.0c00334 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Lo, Pui Kin Tony
Oliver, Gwyndaf A.
Willis, Michael C.
Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title_full Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title_fullStr Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title_full_unstemmed Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title_short Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines
title_sort sulfinamide synthesis using organometallic reagents, dabso, and amines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304903/
https://www.ncbi.nlm.nih.gov/pubmed/32286844
http://dx.doi.org/10.1021/acs.joc.0c00334
work_keys_str_mv AT lopuikintony sulfinamidesynthesisusingorganometallicreagentsdabsoandamines
AT olivergwyndafa sulfinamidesynthesisusingorganometallicreagentsdabsoandamines
AT willismichaelc sulfinamidesynthesisusingorganometallicreagentsdabsoandamines