I want to selectively reduce secondary amide in my compound in presence of nitro and Boc groups
Dear Mustafa,
The following paper covers the answer to your question:
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*
Graduate School of Engineering Sciences, Institute for Materials Chemistry and Engineering, Kyushu University, Kasuga, Fukuoka 816-8580, Japan
J. Am. Chem. Soc., 2009, 131 (41), pp 15032–15040
DOI: 10.1021/ja9055307
Publication Date (Web): September 28, 2009
The synergetic effect of two Si−H groups leads to efficient reduction of carboxamides to amines by platinum catalysts under mild conditions. The rate of the reaction is dependent on the distance of two Si−H groups; 1,1,3,3-tetramethyldisiloxane (TMDS) and 1,2-bis(dimethylsilyl)benzene are found to be an effective reducing reagent. The reduction of amides having other reducible functional groups such as NO2, CO2R, CN, C═C, Cl, and Br moieties proceeds with these groups remaining intact, providing a reliable method for the access to functionalized amine derivatives. The platinum-catalyzed reduction of amides with polymethylhydrosiloxane (PMHS) also proceeds under mild conditions. The reaction is accompanied by automatic removal of both platinum and silicon wastes as insoluble silicone resin, and the product is obtained by simple extraction. A mechanism involving double oxidative addition of TMDS to a platinum center is discussed.
Hoping this will be helpful,
Rafik
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: nagasima cm.kyushu-u.ac.jp
S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc., 2009, 131, 15032-15040.
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.
see article for more examples
The Ruthenium-Catalyzed Reduction and Reducti
I have a book that might be useful: The chemistry of amino, nitroso, nitro and related groups 1996 Part 1 - Patai.
Send me an e-mail and I attach it to my response. Greettings
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