Organic Letters
Organic Letters
5 years ago

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles

Palladium-Catalyzed Dehydrogenative Difunctionalization of Aminoalkenes with Aminals as Oxidants and Electrophiles
Hanmin Huang, Xibing Zhou, Bangkui Yu, Lixin Li
A novel palladium-catalyzed aminomethylamination of aminoalkenes with an aminal, functioning not only as an aminomethylation reagent but also as an oxidant, was developed. This direct and operationally simple protocol provides a fundamentally novel and unique approach toward the synthesis of 2-(2-aminoethyl)indoles and 2-(2-aminoethyl)pyrrolidines, which are important building blocks in synthetic organic chemistry. The unity of this method was highlighted by the rapid synthesis of Alosetron, a drug used for the treatment of irritable bowel syndrome.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02203

DOI: 10.1021/acs.orglett.7b02203

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