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The Aminomethylation of Electron-Rich Aromatics with an N -Silyl- N , O -Acetal Catalyzed by a Metal Triflate-TMSCl System: Facile Synthesis of Aromatic Primary Amines, 1-Aryl-trichloroethylamines

2002; American Chemical Society; Volume: 68; Issue: 2 Linguagem: Inglês

10.1021/jo026465k

1520-6904

Norio Sakai, Maki Hirasawa, Toshihiro Hamajima, Takeo Konakahara,

Asymmetric Hydrogenation and Catalysis

The copper(II) triflate- and hafnium(IV) triflate-catalyzed aminomethylation of indole (2) with an N-silyl-N,O-acetal 1 containing a trichloromethyl group provides the primary amine derivative (3a) in modest yield. When 1 equiv of trimethylchlorosilane (TMSCl) was added to the reaction mixture, the reaction proceeded smoothly, and the yield of 3a was dramatically improved (>90%). The use of this catalytic system permitted the introduction of an aminomethyl group onto indoles 2a-h bearing a variety of functional groups, which appears to deactivate the Lewis acid, in 52-92% yields. Hf(OTf)4-doped TMSCl catalyzed the successful aminomethylation of various electron-rich aromatic compounds 4a-j to produce 1-aryl-trichloroethylamine derivatives 5a-j.