title: Negishi Cross-Coupling Is Compatible with a Reactive B-Cl Bond: Development of a Versatile Late-Stage Functionalization of 1,2-Azaborines and Its Application to the Synthesis of New BN Isosteres of Naphthalene and Indenyl.
abstract: The compatibility of the Negishi cross-coupling reaction with the versatile B-Cl functionality has been demonstrated in the context of late-stage functionalization of 1,2-azaborines. Alkyl-, aryl-, and alkenylzinc reagents have been utilized for the functionalization of the triply orthogonal precursor 3-bromo-1-(tert-butyldimethylsilyl)-2-chloro-1,2-dihydro-1,2-azaborine (2) to furnish new 2,3-substituted monocyclic 1,2-azaborines. This methodology has enabled the synthesis of previously elusive BN-naphthalene and BN-indenyl structures from a common intermediate.
authors.affiliation: Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
authors.forename: Alec N
authors.initials: AN
authors.lastname: Brown
authors.affiliation: Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
authors.forename: Bo
authors.initials: B
authors.lastname: Li
authors.affiliation: Department of Chemistry, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States.
authors.forename: Shih-Yuan
authors.initials: SY
authors.lastname: Liu
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry*
chemical_list: C556261:1,2-azaborine; D001896:Boron Compounds; D007192:Indenes; D009281:Naphthalenes; C031721:naphthalene; D009584:Nitrogen