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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2020
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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 |
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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 |
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