title: Accessing molecularly complex azaborines: palladium-catalyzed Suzuki-Miyaura cross-couplings of brominated 2,1-borazaronaphthalenes and potassium organotrifluoroborates.
abstract: Despite their potential applications in both medicinal chemistry and materials science, there have been limited reports on the functionalization of 2,1-borazaronaphthalenes since their discovery in 1959. To access new chemical space and build molecular complexity, the Suzuki-Miyaura cross-coupling of brominated 2,1-borazaronaphthalenes has been investigated. The palladium-catalyzed cross-coupling proceeds with an array of potassium (hetero)aryltrifluoroborates in high yield with low catalyst loadings under mild reaction conditions. By the use of a high-yielding bromination of various 2,1-borazaronaphthalenes to generate electrophilic azaborine species, a library of 3-(hetero)aryl and 3,6-diaryl-2,1-borazaronaphthalenes has been synthesized.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Steven R
authors.initials: SR
authors.lastname: Wisniewski
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011188:Potassium / Q000737:chemistry*
chemical_list: D001372:Aza Compounds; D001881:Borates; D001896:Boron Compounds; D009281:Naphthalenes; D009942:Organometallic Compounds; D010165:Palladium; D011188:Potassium