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Copper-Catalyzed Transformations Using Cu-H, Cu-B, and Cu-Si as Active Catalyst Species.
Chem Rec
October 2016
Department of Energy and Hydrocarbon chemistry Graduate School of Engineering, Kyoto University, Kyoto, 615-8510, Japan.
This review summarizes transformations using copper hydride (Cu-H), boryl copper (Cu-B) or silyl copper (Cu-Si) as active catalyst species. Semihydrogenation, hydroboration, and hydrocarboxylation have been developed using Cu-H as active catalyst species. Preferential reduction of sterically hindered ketones is accompanied by Cu-H species bearing a bowl-shaped phosphine as a crucial ligand.
View Article and Find Full Text PDFMechanistic Insight into the Copper-Catalyzed Regiodivergent Silacarboxylation of Allenes with CO2.
Chem Asian J
August 2016
State Key Laboratory for Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials.
DFT calculations were performed to investigate the detailed reaction mechanisms in the copper-catalyzed regiodivergent silacarboxylation of allenes. According to our calculations, the catalysis would bifurcate at the allene silylcupration step, followed by CO2 insertion, eventually leading to the carboxylated vinylsilane or allylsilane products. The gaps between the two silylcupration barriers were predicted to be -2.
View Article and Find Full Text PDFCopper-catalyzed regiodivergent silacarboxylation of allenes with carbon dioxide and a silylborane.
J Am Chem Soc
December 2014
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
A regiodivergent silacarboxylation of allenes under a CO2 atmosphere with PhMe2Si-B(pin) as a silicon source in the presence of a copper catalyst at 70 °C has been developed. The regioselectivity of the reaction is successfully reversed by the proper choice of ligand; carboxylated vinylsilanes are obtained with rac-Me-DuPhos as the ligand, whereas the use of PCy3 affords carboxylated allylsilanes. Thus, two different carboxylated silanes can be selectively and regiodivergently synthesized from a single allene substrate.
View Article and Find Full Text PDFCopper-catalyzed silacarboxylation of internal alkynes by employing carbon dioxide and silylboranes.
Angew Chem Int Ed Engl
November 2012
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
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