Regioselectivity of Selenium-Mediated Carbonylation of Organolithium Compounds with Carbon Monoxide

Shin-ichi Fujiwara Department of Chemistry, Osaka Dental University, Osaka, Japan

Akira Nishiyama Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan

Kazuhiro Okada Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan

Hajime Maeda Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan

Tsutomu Shin-ike Department of Chemistry, Osaka Dental University, Osaka, Japan

Noboru Sonoda Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan

Nobuaki Kambe Department of Applied Chemistry, Graduate School of Engineering, Osaka University, Osaka, Japan

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Abstract

Regioselectivity of selenium-mediated carbonylation of organolithium compounds with carbon monoxide has been investigated. The reactions of lithium enolates of 2,2-dicyclohexyl aldehyde and 1,1-dicyclohexylpropane-2-one with selenium and carbon monoxide afforded the corresponding selenocarbonates by carbonylation at the enolate oxygen as the main product. Carbonylation of nitrogen-containing heterocycles can give either C- or N-carbonylation product, but diphenyl(4-pyridyno)methane, imidazole, and pyrazole afford only corresponding carbamoselenoates via N-carbonylation.

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Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday.

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Regioselectivity of Selenium-Mediated Carbonylation of Organolithium Compounds with Carbon Monoxide

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Regioselectivity of Selenium-Mediated Carbonylation of Organolithium Compounds with Carbon Monoxide

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