1005460-24-1Relevant articles and documents
Hydrosilane reduction of tertiary carboxamides by iron carbonyl catalysts
Sunada, Yusuke,Kawakami, Hiroko,Imaoka, Tsuyoshi,Motoyama, Yukihiro,Nagashima, Hideo
, p. 9511 - 9514 (2009)
Fox in the carboxamide: Reduction of tertiary carboxamides to their corresponding amines is catalyzed by [Fe(CO)5] or [Fe 3(CO)12], using 1,1,3,3tetramethyldlsiloxane (TMDS) as the reducing agent. The reaction proceeds under either thermal or photochemical conditions. Unlike the hydrosilane reduction of amides using platinum or ruthenlum catalysts, TMDS preferentially reduces a nitro group, even in the presence of competing amides.
Dioxygen-promoted Pd-catalyzed aminocarbonylation of organoboronic acids with amines and CO: A direct approach to tertiary amides
Ren, Long,Li, Xinwei,Jiao, Ning
supporting information, p. 5852 - 5855 (2016/11/29)
A direct approach from organoboronic acids and amines to tertiary amides via Pd-catalyzed aerobic aminocarbonylation has been developed. The presence of O2 significantly promotes the efficiency of this transformation. This method uses commercially available organoboronic acids and cheap CO and O2 (1 atm), which renders amides an easy synthesis with broad substrate scope and high functional group tolerance.
Practical access to amines by platinum-catalyzed reduction of carboxamides with hydrosilanes: Synergy of dual Si-H groups leads to high efficiency and selectivity
Hanada, Shiori,Tsutsumi, Emi,Motoyama, Yukihiro,Nagashima, Hideo
supporting information; experimental part, p. 15032 - 15040 (2010/01/29)
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, CdC, 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.
Functional group-selective poisoning of molecular catalysts: A ruthenium cluster-catalysed highly amide-selective silane reduction that does not affect ketones or esters
Sasakuma, Hidehiro,Motoyama, Yukihiro,Nagashima, Hideo
, p. 4916 - 4918 (2008/09/17)
The addition of amines eliminates the catalytic activity of a triruthenium cluster in the hydrosilane reduction of ketones and esters without affecting the rate of reduction of amides; selective reduction of the amide group in amido ketones and amido esters is accomplished. The Royal Society of Chemistry.
