title: Organoborane catalyzed regioselective 1,4-hydroboration of pyridines.
abstract: A bulky organoborane Ar(F)2BMe (Ar(F) = 2,4,6-tris(trifluoromethyl)phenyl, 1) has been synthesized. In C6D6 solution this organoborane and pyridine form a frustrated Lewis pair. Under mild conditions, 1 can efficiently catalyze 1,4-hydroboration of a series of pyridines. This reaction is highly chemo- and regioselective. The reaction intermediate, a boronium complex [Py2Bpin][Ar(F)2B(H)Me] (3), was characterized in solution by NMR spectroscopy, which was also confirmed by DFT calculation.
authors.affiliation: Collaborative Innovation Center of Chemistry for Energy Material, Shanghai Key Laboratory of Molecular Catalysis and Innovative Material, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200433, China.
authors.forename: Xiaoting
authors.initials: X
authors.lastname: Fan
authors.affiliation: Collaborative Innovation Center of Chemistry for Energy Material, Shanghai Key Laboratory of Molecular Catalysis and Innovative Material, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200433, China.
authors.forename: Junhao
authors.initials: J
authors.lastname: Zheng
authors.affiliation: Collaborative Innovation Center of Chemistry for Energy Material, Shanghai Key Laboratory of Molecular Catalysis and Innovative Material, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200433, China.
authors.forename: Zhen Hua
authors.initials: ZH
authors.lastname: Li
authors.affiliation: Collaborative Innovation Center of Chemistry for Energy Material, Shanghai Key Laboratory of Molecular Catalysis and Innovative Material, Department of Chemistry, Fudan University, Handan Road 220, Shanghai, 200433, China.
authors.forename: Huadong
authors.initials: H
authors.lastname: Wang
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D011725:Pyridines