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author:

Yuan, Tao (Yuan, Tao.) [1] | Sun, Luyang (Sun, Luyang.) [2] | Wu, Ziwei (Wu, Ziwei.) [3] | Wang, Rong (Wang, Rong.) [4] | Cai, Xu (Cai, Xu.) [5] | Lin, Wei (Lin, Wei.) [6] | Zheng, Meifang (Zheng, Meifang.) [7] | Wang, Xinchen (Wang, Xinchen.) [8]

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Abstract:

The direct reduction of inert planar arenes and heteroarenes with visible light remains rarely explored, as the energy of one visible-light photon is unable to overcome the stabilization of aromatics. Here we report a system based on boron carbonitride semiconductor, which can reduce arenes and heteroarenes in water under blue light irradiation. The system features the advantage of low-cost, high-efficiency, facile separation, benign environmental profile and broad substituent tolerance. The methodology can be extended to late-stage functionalization and/or deuteration of drugs, hormones and axially chiral compounds with conserved chirality. Moreover, gram-scale synthesis is successfully implemented with catalyst recycling. Mechanistic investigations support a consecutive blue-light-induced energy and electron transfer process, which accumulates sufficient energy to reduce arenes to arene anions by absorbing two photons successively. The metal-free system introduces a simple and sustainable reactivity mode for semiconductor photocatalysts and enriches the chemical toolkit for a class of demanding and valuable organic transformations. [Figure not available: see fulltext.]. © 2022, The Author(s), under exclusive licence to Springer Nature Limited.

Keyword:

Aromatic hydrocarbons Carbon nitride Electron transport properties Photons Stereochemistry

Community:

  • [ 1 ] [Yuan, Tao]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 2 ] [Sun, Luyang]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 3 ] [Wu, Ziwei]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 4 ] [Wang, Rong]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 5 ] [Cai, Xu]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 6 ] [Lin, Wei]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 7 ] [Zheng, Meifang]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 8 ] [Zheng, Meifang]Fujian Science & Technology Innovation Laboratory for Chemical Engineering of China, Quanzhou, China
  • [ 9 ] [Wang, Xinchen]State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University, Fuzhou, China
  • [ 10 ] [Wang, Xinchen]Fujian Science & Technology Innovation Laboratory for Chemical Engineering of China, Quanzhou, China

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Source :

Nature Catalysis

Year: 2022

Issue: 12

Volume: 5

Page: 1157-1168

3 7 . 8

JCR@2022

4 2 . 9 0 0

JCR@2023

ESI HC Threshold:74

JCR Journal Grade:1

CAS Journal Grade:1

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 48

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 1

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