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Amination of Aryl Boronic Acids with Alkylnitrites: A Convenient Complement to Cu-Promoted Reductive Amination.

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Copper-catalyzed amination of aryl boronic acids with alkylnitrites leading to symmetrical diarylamines with a practical 50-80% yield was elaborated. Two C(sp2)-N bonds are formed in the one-pot process under mild… Click to show full abstract

Copper-catalyzed amination of aryl boronic acids with alkylnitrites leading to symmetrical diarylamines with a practical 50-80% yield was elaborated. Two C(sp2)-N bonds are formed in the one-pot process under mild conditions. This new approach to diarylamines is a complement to the Cu-assisted reductive amination of aryl boronic acids avoiding preliminary synthesis of nitrosoarenes. The possible reaction scheme based on quantum chemical calculations was suggested, clarifying key intermediates.

Keywords: acids alkylnitrites; boronic acids; reductive amination; amination; amination aryl; aryl boronic

Journal Title: Organic letters
Year Published: 2019

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