Metal-free directed sp2-C-H borylation

被引：207

作者：

Lv, Jiahang ^{[1
,2
]}

Chen, Xiangyang ^{[3
]}

Xue, Xiao-Song ^{[3
,4
]}

Zhao, Binlin ^{[1
]}

Liang, Yong ^{[1
]}

Wang, Minyan ^{[1
]}

Jin, Liqun ^{[5
]}

Yuan, Yu ^{[2
]}

Han, Ying ^{[2
]}

Zhao, Yue ^{[1
]}

Lu, Yi ^{[1
]}

Zhao, Jing ^{[1
]}

Sun, Wei-Yin ^{[1
]}

Houk, Kendall. N. ^{[3
]}

Shi, Zhuangzhi ^{[1
,2
,4
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, Chem & Biomed Innovat Ctr ChemBIC, State Key Lab Coordinat Chem, Nanjing, Jiangsu, Peoples R China

[2] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou, Jiangsu, Peoples R China

[3] Univ Calif Los Angeles, Dept Chem & Biochem, 405 Hilgard Ave, Los Angeles, CA 90024 USA

[4] Nankai Univ, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin, Peoples R China

[5] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou, Zhejiang, Peoples R China

来源：

NATURE | 2019年 / 575卷 / 7782期

基金：

美国国家科学基金会; 中国国家自然科学基金;

关键词：

C-H ACTIVATION; BONDS; ARYLATION; INDOLES;

D O I：

10.1038/s41586-019-1640-2

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials(1). The discovery of simpler, milder and more efficient approaches to organoborons can open additional routes to diverse substances(2-5). Here we show a general method for the directed C-H borylation of arenes and heteroarenes without the use of metal catalysts. C7- and C4-borylated indoles are produced by a mild approach that is compatible with a broad range of functional groups. The mechanism, which is established by density functional theory calculations, involves BBr3 acting as both a reagent and a catalyst. The potential utility of this strategy is highlighted by the downstream transformation of the formed boron species into natural products and drug scaffolds.

引用

页码：336 / +

页数：6

共 30 条

[1]

Barluenga J, 2009, NAT CHEM, V1, P494, DOI [10.1038/NCHEM.328, 10.1038/nchem.328]

[2] Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].