Proceedings of the Symposium on Progress in Organic Reactions and Syntheses
29th Symposium on Progress in Organic Reactions and Syntheses
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Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan

Oral Presentations
Mercuric Triflate-Catalyzed Enyne- and Arylyne-Cyclization
*Mugio Nishizawa, Veejendra K. Yadav, Mariusz Skwarczynski, Hiroko Takao, Hiroshi Imagawa, Takumichi Sugihara
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Keywords: mercuric triflate, catalyst, enyne cyclization, arylyne cyclization
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Pages 6-7

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Abstract

We found our original olefin cyclization agent Hg(OTf)2 exhibits remarkable catalytic activity for the hydroxylative cyclization of 1,6-enynes such to give exomethylene five-membered carbocycles in excellent yield. On the other hand Hg(OTf)2-(TMU)3 complex is effective as a catalyst for the arylyne cyclization affording dihydronaphtalens. Catalytic activity of both reactions reached up to 1,000 cycles. The reaction should involve a protodemercuration step of the vinylmercuric intermediate induced by TfOH, formed in situ, regenerating catalyst.

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© 2003 The Pharmaceutical Society of Japan
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