Citation: Bin Wang, Jiawei Ma, Hongyuan Ren, Shuo Lu, Jingkai Xu, Yong Liang, Changsheng Lu, Hong Yan. Chemo-, site-selective reduction of nitroarenes under blue-light, catalyst-free conditions[J]. Chinese Chemical Letters, ;2022, 33(5): 2420-2424. doi: 10.1016/j.cclet.2021.11.023 shu

Chemo-, site-selective reduction of nitroarenes under blue-light, catalyst-free conditions

State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China

yongliang@nju.edu.cn

luchsh@nju.edu.cn

hyan1965@nju.edu.c

Received Date: 9 October 2021
Revised Date: 4 November 2021
Accepted Date: 5 November 2021
Available Online: 11 November 2021

Figures(5)

The tandem reaction of photoinduced double hydrogen-atom transfer and deoxygenative transborylation for chemo- and site-selective reduction of nitroarenes into aryl amines under catalyst-free, room temperature conditions was disclosed in excellent yields. In this reaction, isopropanol (ⁱPrOH) was used as hydrogen donor and tetrahydroxydiboron [B₂(OH)₄] as deoxygenative reagent with green, cheap, and commercially available credentials. In particular, a wide range of reducible functional groups such as halogen (-Cl, -Br and even -I), alkenyl, alkynyl, aldehyde, ketone, carboxyl, and cyano are all tolerated. Moreover, the reaction preferentially reduces the nitro group at the electron-deficient site over another nitro group in the same molecule. A detailed mechanistic investigation in combination of experiments and theoretical calculations gave a reasonable explanation for the reaction pathway.
- Nitroarenes,
- Selective,
- Reduction,
- Catalyst-free,
- Photoinduced,
- Transborylation
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