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An Acid-Controlled Method for the Regioselective Functionalization of Anilines over Aliphatic Amines
Bowen Li1, Yulun Hu1, Gregory P Tochtrop1
1Department of Chemistry, Case Western Reserve University Millis Hall 410, 2080 Adelbert Road, Cleveland, Ohio, 44106, USA.
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Regioselective transformations at similar functional groups are of paramount importance in organic synthesis. Traditional strategies towards regioselective functionalization include serial protection/deprotection and sequential synthesis. Modern organic synthesis emphasizes pathway efficiency and protecting group free routes with a goal of exploiting inherent differences in reactivity. This study reports a method for the regioselective functionalization of anilines over aliphatic amines. Utilizing classic conditions for the Baeyer-Mills reaction, anilines were shown to react preferentially in the presence of aliphatic amines. Subsequently, this principle of reactivity was extended to other electrophiles and conditions.
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