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Sulfinamide synthesis using organometallic reagents, DABSO, and amines

Abstract:

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 perf...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/acs.joc.0c00334

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0002-0636-6471
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry More from this journal
Volume:
85
Issue:
9
Pages:
5753-5760
Publication date:
2020-04-14
Acceptance date:
2020-04-06
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Keywords:
Pubs id:
1098991
Local pid:
pubs:1098991
Deposit date:
2020-04-07

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