Journal article
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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(Accepted manuscript, 317.4KB)
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- Publisher copy:
- 10.1021/jacs.8b11039
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Authors
Bibliographic Details
- 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
Item Description
- Language:
- English
- Pubs id:
-
pubs:966072
- UUID:
-
uuid:51cde690-8721-4a6c-a200-c44988c95200
- Local pid:
- pubs:966072
- Deposit date:
- 2019-02-18
Terms of use
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2019
- Rights statement:
- © 2019 American Chemical Society.
- Notes:
- This is the accepted manuscript version of the article. The final version is available online from American Chemical Society. at: https://doi.org/10.1021/jacs.8b11039
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