Reductive Addition of the Benzenethiyl Radical to Alkynes by Amine-Mediated Single Electron Transfer Reaction to Diphenyl Disulfide

Reductive Addition of the Benzenethiyl Radical to Alkynes by Amine-Mediated Single Electron Transfer Reaction to Diphenyl Disulfide

Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compounds are also presented.

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Veröffentlicht in:Organic letters 2009-08, Vol.11 (15), p.3298-3301
Hauptverfasser: Taniguchi, Tsuyoshi, Fujii, Tatsuya, Idota, Atsushi, Ishibashi, Hiroyuki
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Amines - chemistry
Benzene - chemistry
Cyclization
Disulfides - chemistry
Electron Transport
Electrons
Oxidation-Reduction
Propylamines - chemistry
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Beschreibung
Zusammenfassung:Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compounds are also presented.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol901084k