title: ortho-Selective nucleophilic addition of amines to 3-borylbenzynes: synthesis of multisubstituted anilines by the triple role of the boryl group.
abstract: Nucleophilic addition of amines to 3-[(dan)boryl]benzynes (dan = 1,8-diaminonaphthalene) generated by a fluoride ion proceeded with high ortho-selectivity to give 2-borylaniline derivatives, under conditions that are tolerant to various functional groups. The (dan)boryl group of the adduct was hydrolyzed into a boronic acid under acidic conditions, which could further serve for various C-C, C-O, C-N, and C-H bond-formation reactions. The overall process provides a promising entry for preparing multisubstituted aniline derivatives.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Takagi
authors.forename: Takashi
authors.initials: T
authors.lastname: Ikawa
authors.forename: Kozumo
authors.initials: K
authors.lastname: Saito
authors.forename: Shigeaki
authors.initials: S
authors.lastname: Masuda
authors.forename: Toyohiro
authors.initials: T
authors.lastname: Ito
authors.forename: Shuji
authors.initials: S
authors.lastname: Akai
mesh_terms: D000588:Amines / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D000588:Amines; D000814:Aniline Compounds; D001555:Benzene Derivatives; D001896:Boron Compounds; C023650:aniline