Organoborane Catalyzed Regioselective 1,4-Hydroboration of Pyridines

被引：112
作者：
Fan, Xiaoting [1 ]
Zheng, Junhao [1 ]
Li, Zhen Hua [1 ]
Wang, Huadong [1 ]
机构：
[1] Fudan Univ, Collaborat Innovat Ctr Chem Energy Mat, Shanghai Key Lab Mol Catalysis & Innovat Mat, Dept Chem, Handan Rd 220, Shanghai 200433, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 15期
关键词：
FRUSTRATED LEWIS PAIRS; B(C6F5)(3)-CATALYZED HYDROSILATION; ASYMMETRIC HYDROGENATION; HANTZSCH ESTERS; HYDROSILYLATION; REDUCTION; CHEMISTRY; 1,2-DIHYDROPYRIDINES; REGENERATION; ACTIVATION;
D O I：
10.1021/jacs.5b03147
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A bulky organoborane (Ar2BMe)-B-F (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 [Py(2)Bpin][(Ar2B)-B-F(H)Me] (3), was characterized in solution by NMR spectroscopy, which was also confirmed by DFT calculation.
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页码：4916 / 4919
页数：4
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