Palladium(II)-Catalyzed Enantioselective Synthesis of α-(Trifluoromethyl)arylmethylamines

详细信息    查看全文

• 作者：Thomas Johnson ; Bo Luo ; Mark Lautens
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：June 17, 2016
• 年：2016
• 卷：81
• 期：12
• 页码：4923-4930
• 全文大小：467K
• 年卷期：0
• ISSN：1520-6904

文摘

We describe a method for the synthesis of α-(trifluoromethyl)arylmethylamines that consists of the palladium(II)-catalyzed addition of arylboroxines to imines derived from trifluoroacetaldehyde. Palladium acetate is used as a catalyst with electron-neutral or electron-rich arylboroxines, and it was found that addition of an ammonium or silver salt was crucial to promote the reaction of electron-poor boroxines. With (S)-t-Bu-PyOX as the chiral ligand, this method delivers a variety of α-trifluoromethylated amines in 57–91% yield and with greater than 92% ee in most cases.