title: Aminoboration: Addition of B-N σ Bonds across C-C π Bonds.
abstract: 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 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 π bond and the B-N σ bond simultaneously.
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
authors.forename: Eugene
authors.initials: E
authors.lastname: Chong
authors.affiliation: Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
authors.forename: Suzanne A
authors.initials: SA
authors.lastname: Blum
mesh_terms: D000588:Amines / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D006571:Heterocyclic Compounds / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry
chemical_list: D000588:Amines; D001896:Boron Compounds; D006571:Heterocyclic Compounds; D007211:Indoles; D011758:Pyrroles; C013231:pyrroline