Metal-free directed sp2-C–H borylation

Jiahang Lv, Xiangyang Chen, Xiao-Song Xue, Binlin Zhao, Yong Liang, Minyan Wang, Liqun Jin, Yu Yuan, Ying Han, Yue Zhao, Yi Lu, Jing Zhao, Wei-Yin Sun, Kendall. N. Houk () and Zhuangzhi Shi ()
Additional contact information
Jiahang Lv: Nanjing University
Xiangyang Chen: University of California, Los Angeles
Xiao-Song Xue: University of California, Los Angeles
Binlin Zhao: Nanjing University
Yong Liang: Nanjing University
Minyan Wang: Nanjing University
Liqun Jin: Zhejiang University of Technology
Yu Yuan: Yangzhou University
Ying Han: Yangzhou University
Yue Zhao: Nanjing University
Yi Lu: Nanjing University
Jing Zhao: Nanjing University
Wei-Yin Sun: Nanjing University
Kendall. N. Houk: University of California, Los Angeles
Zhuangzhi Shi: Nanjing University

Nature, 2019, vol. 575, issue 7782, 336-340

Abstract: Abstract Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can open additional routes to diverse substances2–5. 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.

Date: 2019
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DOI: 10.1038/s41586-019-1640-2

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