The formation of the C�N bond is a critical tool in synthetic organic chemistry based on the abundance of amino groups in pharmaceuticals and natural products.  Conversion of boronate esters into amines is of particular interest since these starting materials are easily accessed through C�H borylation from readily available compounds.  Prior work in our group has demonstrated the transformation of ortho selective C�H borylation of N,N-dimethylaminobenzenes into the corresponding boronate esters.  Various copper-catalyzed amination conditions were then employed to convert the N,N-dimethylaminobenzyl boronate esters into the corresponding secondary and tertiary amines.  Competitive formation of the homocoupled product of the boronate ester was found to occur in both cases.  Substitution on the boronate ester substrate changes the distribution of these products.  The conditions, products, and competition between the amination and homocoupled products will be presented.

Amination of N,N-dimethylaminobenzyl boronate esters under copper-catalyzed conditions

248th National Meeting (2014)

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