Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si-H Groups Leads to High Efficiency and Selectivity

Shiori Hanada, Emi Tsutsumi, Yukihiro Motoyama and Hideo Nagashima*

*Institute for Materials Chemistry and Engineering, Graduate School of Engineering Sciences, Kyushu University, Kasuga, Fukuoka 816-8580, Japan, Email: nagasimacm.kyushu-u.ac.jp

S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc., 2009, 131, 15032-15040.

DOI: 10.1021/ja9055307

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Abstract

1,1,3,3-tetramethyldisiloxane and 1,2-bis(dimethylsilyl)benzene are found to be effective reducing agents for a platinum-catalyzed reduction of carboxamides to amines. The reaction tolerates other reducible functional groups such as NO₂, CO₂R, CN, C═C, Cl, and Br. The product is obtained by simple extraction.

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The Ruthenium-Catalyzed Reduction and Reductive N-Alkylation of Secondary Amides with Hydrosilanes: Practical Synthesis of Secondary and Tertiary Amines by Judicious Choice of Hydrosilanes

S. Hanada, T. Ishida, Y. Motoyama, H. Nagashima, J. Org. Chem., 2007, 72, 7551-7559.

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Key Words

reduction of amides, tetramethyldisiloxane

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ID: J48-Y2009-3040