Photoredox dearomative β-hydroborylation of indoles for the synthesis of borylated indolines

A photocatalysed dearomative β-hydroborylation reaction of indole derivatives with NHC-boranes has been accomplished. This protocol shows a broad substrate scope with moderate to excellent yields, providing a novel and efficient route for the preparation of C2- and C3-borylated indolines, which are...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-12, Vol.11 (1), p.149-155
Main Authors: Yongchan Jian, Wen, Fei, Shang, Jianping, Li, Xiaolong, Liu, Zhenyu, An, Yuanyuan, Wang, Yubin
Format: Article
Language:English
Subjects:
Electron transfer
Energy transfer
Functional materials
Heterocyclic compounds
Indoles
Natural products
Organic chemistry
Single electrons
Substrates
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Summary:A photocatalysed dearomative β-hydroborylation reaction of indole derivatives with NHC-boranes has been accomplished. This protocol shows a broad substrate scope with moderate to excellent yields, providing a novel and efficient route for the preparation of C2- and C3-borylated indolines, which are important structural units in pharmaceuticals, natural products and functional materials. Control experiments elucidated a radical process initiated by photoinduced energy transfer and single-electron transfer for this transformation. Furthermore, gram-scale reactions demonstrated the synthetic value of this method.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01452e