Palladium complex catalyzed reaction of diphenylketene with terminal acetylenes giving disubstituted acetylenes

✍ Scribed by Take-aki Mitsudo; Mamoru Kadokura; Yoshihisa Watanabe

• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 121 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89226-6

✦ Synopsis

The reaction of diphenylketene with terminal acetylenes catalyzed by tetrakis-(triphenylphosphine)palladium gave disubstituted acetylenes in high yields.

Ketenes are known to undergo a variety of charactaristic reactions and to form complexes with transition metals. ') A currently important area in organometallic chemistry is the synthesis and the utilization of transition metal carbene complexes. 2) It has been reported that diphenylketene is a good precursor of a carbene ligande3) However, no application of this feature to organic synthesis has been reported. Here we report the first example of palladium complex catalyzed organic synthesis using a ketene as a source of a carbene moiety.

The reaction of diphenylketene with terminal acetylenes in the presence of a catalytic amount of tetrakis(triphenylphosphinelpalladium(0) gave disubstituted acetylenes (eq. I).