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Please login to access the full content or check if you have access via1.2.3.6.3 Addition of Diaryl Disulfides to Alkynes To Form 1,2-Disulfanylalkenes
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Takacs, J. M.; Vayalakkada, S.; Jiang, X., Science of Synthesis, (2001) 1, 308.
The palladium-catalyzed reaction of disulfides with terminal alkynes 164 (R2 = H) proceeds stereoselectively to give high yields of (Z)-1,2-bis(phenylsulfanyl)alk-1-enes 177 (Scheme 49).[46] The addition of diphenyl disulfide to alkynes proceeds efficiently with tetrakis(triphenylphosphine)palladium(0). In contrast, palladium(II) complexes do not catalyze the reaction. Certain functional groups, e.g. hydroxy, trimethylsilyl, and amino groups, are tolerated in the reaction. In the case of an enyne substrate, the addition reaction takes place chemoselectively on the triple bond. In contrast to the facile reaction of terminal alkynes, the addition of disulfides to internal acetylenes (e.g., 164, R2 = Pr) proceeds poorly.
Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeee ee Meeeeeee Meeeeeeee ee Meeeeee[88]
| M8 | M8 | Meeee (%) | Mee |
|---|---|---|---|
| (MM8)8Me | M | 88 | [88] |
| MM8MM8eMe | M | 88 | [88] |
| M(MM)Me8 | M | 88 | [88] |
| MMMeMM | M | 88 | [88] |
| MM8MM | M | 88 | [88] |
| (MM8)8MM | M | 88 | [88] |
| MMM | M | 88 | [88] |
| MM8MM8 | M | 88 | [88] |
| Me | M | 88 | [88] |
| Me | Me | 8 | [88] |
| MM8M(MM8Me)8MM8MM=MM8 | M | 88 | [88] |
| MM8MMM8MM=MM8 | M | 88 | [88] |
Mee eeeeeeeee eeeee ee Meeeee 88 ee eeeeeeee ee eeeeeee eee eeeeeeeee ee eee (M)-8,8-eee(eeeeeeeeeeeeee)eee-8-eeee 888.[88] Meeeeeeee eeeeeeee ee eee eeeeeeee eeeeeeeee ee e eeeeeeeee(8) eeeeeee eeeeee eeee eee eeeeeeeee(MM) eeeeeeeee eeeeeee 888. Meeeeeeeeeeeee eee eeeeeeeeeeeeeee ee eee eeeeee eeeee eeee eee eeeeeeeeeeeeee(MM) eeeeeee 888 eee 888. Meeeeeeee eeeeeeeeeee ee 888 eeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eee eee eeeeeeee eeeeeee 888.
Meeeee 88 Meeeeeeee ee eee (M)-8,8-Mee(eeeeeeeeeeeeee)eee-8-eeee[88]
Meeeeeeeeeee Meeeeeeee
(M)-8,8-Mee(eeeeeeeeeeeeee)eee-8-eee [888, M8 = (MM8)8Me; M8 = M]; Meeeeee Meeeeeeee:[88]
Meee e eee-eeeeee eeeee eeeeeeee eeee e eeeeee eeeeeeeee, e eeeeeeee eeeeeeee eee, eee eeeee eeeee eeee eeeeee Me(MMe8)8 (88 ee, 8.88 eeee), (MeM)8 (888 ee, 8.8 eeee), eee-8-eee (888 ee, 8.8 eeee), eee eeeeeee (8.8 eM). Mee eeeee ee eee eeee eeeeeee eeeeee eeee eeeeee ee eeee eeeee. Mee eeeeeee eee eeeeeeee eeee eeeeeeee eee 88 e. Meee eee eeeeeeee eee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeee Meeeee, eee eee eeeeeeee eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee MMMM eee eeeeeeeeeee-eeeee eeeeeeeeeeeeee ee eeee eee eeeeeee ee e eeeee eee; eeeee: 888 ee (88%).
References
| [46] | Meeeeeee, M.; Meeee, M.; Meeeeeee, M. M.; Mee, M.; Meeee, M.; Meeeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
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