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.
Taniguchi
Tsuyoshi
T
School of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
Fujii
Tatsuya
T
Idota
Atsushi
A
Ishibashi
Hiroyuki
H
D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D001554:Benzene / Q000737:chemistry; D003500:Cyclization; D004220:Disulfides / Q000737:chemistry*; D004579:Electron Transport; D004583:Electrons; D010084:Oxidation-Reduction; D011437:Propylamines / Q000737:chemistry*
D000480:Alkynes; D000588:Amines; D004220:Disulfides; D011437:Propylamines; C096226:tripropylamine; C053871:diphenyl disulfide; D001554:Benzene