title: A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates.
abstract: Azaborines are an important class of compounds with applications in both medicinal chemistry and materials science. The first borazaronaphthalene, 2-chloro-2,1-borazaronaphthalene, was reported in 1959; however, access to more highly functionalized substructures has been limited because of the harsh reaction conditions required to displace the chloride on boron. A convergent approach has been developed to synthesize disubstituted 2,1-borazaronaphthalenes from N-substituted 2-aminostyrenes and potassium organotrifluoroborates, where the potassium organotrifluoroborate is converted to the active R-BX2 species (X = Cl or F) in situ by addition of a fluorophile. Starting from aryl-, heteroaryl-, alkynyl-, alkenyl-, and alkyltrifluoroborates, a library of highly functionalized 2,1-borazaronaphthalenes were synthesized in one step under mild, transition-metal-free conditions.
authors: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors: Steven R
authors: SR
authors: Wisniewski
authors: Courtney L
authors: CL
authors: Guenther
authors: O Andreea
authors: OA
authors: Argintaru
authors: Gary A
authors: GA
authors: Molander
mesh_terms: D001881:Borates / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*; D028561:Transition Elements / Q000737:chemistry*
chemical_list: C000590897:2-chloro-2,1-borazaronaphthalene; D001881:Borates; D009281:Naphthalenes; D013343:Styrenes; D028561:Transition Elements; D005461:Fluorine; D011188:Potassium