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DOI: 10.1055/s-0029-1218503
Rhodium-Catalyzed Conjugate Alkynylation with TMS-acetylene
Contributor(s):Hisashi Yamamoto, Pingfan LiUniversity of Waterloo, Canada
Enantioselective Rhodium-Catalyzed Conjugate Alkynylation of 5-Benzylidene Meldrum’s Acids with TMS-acetylene
J. Am. Chem. Soc. 2009, 131: 14608-14609
Publication History
Publication Date:
21 December 2009 (online)
Key words
alkynylation - trimethylsilyl-acetylenes - rhodium
Significance
The authors utilized TMS-acetylene for the rhodium/diphosphine complex catalyzed conjugate addition of 5-benzylidene Meldrum’s acids, which are believed to be highly electrophilic acceptors. Similar reactions were previously reported to proceed with phenylacetylene or (triisopropylsilyl)acetylene as nucleophiles.
Comment
The employment of TMS-acetylene opens up lots of opportunities for further derivatizations as shown in this paper. Unfortunately, the substrate scope (i.e., 5-benzylidene Meldrum’s acids) was rather limited. This rhodium-catalyzed conjugate addition would be more powerful if more acceptor substrates could be used.