Platinum complex catalyzed reaction of tributyltin cyanide with alkynes |
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Authors: | Yasushi Obora Angelo S. Baleta Makoto Tokunaga Yasushi Tsuji |
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Affiliation: | Catalysis Research Center and Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0811, Japan |
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Abstract: | In the presence of a catalytic amount (5 mol%) of a platinum complex, tributyltin cyanide (1) reacts with dimethyl- (2a) or diethyl acetylenedicarboxylate (2b) to afford cyanostannylation adducts (3a, b) in excellent yields. The reaction proceeds highly selectively affording only a (Z)-isomer. The compounds 3a, b are novel products which possess synthetically useful cyano, alkenylstannyl and alkoxycarbonyl functionalities in the same molecule. Two alkoxycarbonyl functionalities may be indispensable on each alkyne carbon to accomplish the cyanostannylation reaction. Reaction with terminal alkynes gave the stannylated product (6). |
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Keywords: | Cyanostannylation Tributyltin cyanide Transition-metal-complex catalyst Internal alkyne Terminal alkyne |
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