Metal-Free Selective Borylation of Arenes by a Diazadiborinine via C-H/C-F Bond Activation and Dearomatization

被引：30
|
作者：
Su, Yuanting [1 ]
Do, Dinh Cao Huan [1 ]
Li, Yongxin [1 ]
Kinjo, Rei [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 35期
关键词：
PHOTOINDUCED BORYLATION; ADDITIVE-FREE; B(CN)(3)(2-);
D O I：
10.1021/jacs.9b06022
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A newly developed annulated 5-chlorinated 1,3,2,5-diazadiborinine derivative (4) selectively activates a C-H bond of benzene (C6H6) and 1,3-di(trifluoromethyl)benzene, as well as a C-F bond in partially fluorinated arenes, to furnish borylation products under catalyst-, metal-, and irradiation-free conditions. Moreover, 4 readily undergoes a reversible dearomative coupling reaction with polycyclic aromatic hydrocarbons to afford diboration products. The latter represents the first reversible intermolecular dearomative diboration of arenes.
引用
收藏
页码：13729 / 13733
页数：5
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