Synthesis of 1,1-disubstituted olefins via catalytic alkyne hydrothiolation/Kumada cross-coupling.
Using recently developed methodology for the regioselective formation of branched alkyl vinyl sulfides, we report a convenient route to 1,1-disubstituted olefins. We demonstrate that n-propanethiol successfully undergoes catalytic alkyne hydrothiolation with both aryl and aliphatic alkynes using Tp*Rh(PPh3)2 as the catalyst. The resulting vinyl sulfides undergo Kumada cross-coupling to afford the desired disubstituted alkene. Both two-step and one-pot procedures are reported.
Sabarre
Anthony
A
Department of Chemistry, 2036 Main Mall, University of British Columbia, Vancouver, BC, Canada V6T 1Z1.
Love
Jennifer
J
D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D009532:Nickel / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D000475:Alkenes; D000480:Alkynes; D013438:Sulfhydryl Compounds; D009532:Nickel