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Aminoboration: Addition of B-N ? Bonds across C-C ? Bonds.

ABSTRACT: This communication demonstrates the first catalytic aminoboration of C-C ? bonds by B-N ? bonds and its application to the synthesis of 3-borylated indoles. The regiochemistry and broad functional group compatibility of this addition reaction enable substitution patterns that are incompatible with major competing technologies. This aminoboration reaction effects the formation of C-B and C-N bonds in a single step from aminoboronic esters, which are simple starting materials available on the gram scale. This reaction generates synthetically valuable N-heterocyclic organoboron compounds as potential building blocks for drug discovery. The working mechanistic hypothesis involves a bifunctional Lewis acid/base catalysis strategy involving the combination of a carbophilic gold cation and a trifluoroacetate anion that activate the C-C ? bond and the B-N ? bond simultaneously.

SUBMITTER: Chong E

PROVIDER: S-EPMC4544320 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Aminoboration: Addition of B-N σ Bonds across C-C π Bonds.

Chong Eugene E Blum Suzanne A SA

Journal of the American Chemical Society 20150810 32

This communication demonstrates the first catalytic aminoboration of C-C π bonds by B-N σ bonds and its application to the synthesis of 3-borylated indoles. The regiochemistry and broad functional group compatibility of this addition reaction enable substitution patterns that are incompatible with major competing technologies. This aminoboration reaction effects the formation of C-B and C-N bonds in a single step from aminoboronic esters, which are simple starting materials available on the gram ...[more]

PMID: 26238962

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