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 (free Supporting Information)
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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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S. Hanada, T. Ishida, Y. Motoyama, H. Nagashima, J. Org. Chem., 2007, 72, 7551-7559.