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

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

DOI: 10.1021/jo070591c

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Abstract

A triruthenium cluster catalyzes the reaction of secondary amides with hydrosilanes, yielding a mixture of secondary amines, tertiary amines, and silyl enamines. Production of secondary amines with complete selectivity is achieved by the use of higher concentration of the catalyst and bifunctional hydrosilanes such as 1,1,3,3-tetramethyldisiloxane followed by acidic workup.

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

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

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Key Words

Reduction of Amides, Tetramethyldisiloxane

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ID: J42-Y2007-2990