Rhodium-catalyzed carbothiolation reaction of 1-alkylthio-1-alkynes

✍ Scribed by Mieko Arisawa; Yui Igarashi; Yoko Tagami; Masahiko Yamaguchi; Chizuko Kabuto

• Book ID: 104098766
• Publisher: Elsevier Science
• Year: 2011
• Tongue: French
• Weight: 651 KB
• Volume: 52
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.12.065

✦ Synopsis

A rhodium complex derived from RhH(PPh 3 ) 4 and Me 2 PhP catalyzed the carbothiolation reaction of 1alkylthio-1-alkynes and 1,4-diaryl-1,3-butadiynes giving (Z)-4-alkylthio-4-aryl-3-arylethynyl-3-buten-1-ynes. Terminal alkynes such as 1-decyne and (t-butylthio)acetylene underwent the carbothiolation reaction using a RhH(PPh 3 ) 4 -dppb catalyst. The reactions proceeded via cis-addition with C-C bond formation at the less hindered acetylene carbon.