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Direct transformation of terminal alkynes into amidines by a silver-catalyzed four-component reaction

Abstract:
An unprecedented conversion of terminal alkynes into N-sulfonimidamides (amidines) is reported by a silver-catalyzed, one-pot, four-component reaction with TMSN3, sodium sulfinate, and sulfonyl azide. The reaction scope includes both aromatic and aliphatic alkynes. A possible cascade reaction mechanism, consisting of alkyne hydroazidation, sulfonyl radical addition, 1,3-dipolar cycloaddition by TMSN3, and retro-1,3-dipolar cycloaddition, is proposed. TMSN3 is found to play an essential role in each step of the reaction.
Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/jacs.8b11039

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Oxford college:
Jesus College
Role:
Author
ORCID:
0000-0002-4149-0494
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Publisher:
American Chemical Society Publisher's website
Journal:
Journal of the American Chemical Society Journal website
Volume:
141
Issue:
4
Pages:
1593-1598
Publication date:
2019-01-22
Acceptance date:
2019-01-22
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pmid:
30667220
Source identifiers:
966072
Language:
English
Pubs id:
pubs:966072
UUID:
uuid:51cde690-8721-4a6c-a200-c44988c95200
Local pid:
pubs:966072
Deposit date:
2019-02-18

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