![(2R,6S)-6-[(Benzyloxy)methyl]-4-{[(2-methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid structure](https://static.chemtradehub.com/structs/109/1093085-91-6-3382.webp "(2R,6S)-6-[(Benzyloxy)methyl]-4-{[(2-methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid structure")
(2R,6S)-6-[(Benzyloxy)methyl]-4-{[(2-methyl-2-propanyl)oxy]carbonyl}-2-morpholinecarboxylic acid
CAS Number:
1093085-91-6
Molecular Formula:
C18H25NO6
Photoredox dearomative β-hydroborylation of indoles for the synthesis of borylated indolines
Literature Information
Publication Date
2023-11-15
DOI
10.1039/D3QO01452E
Impact Factor
5.281
Authors
Yongchan Jian, Fei Wen, Jianping Shang, Xiaolong Li, Zhenyu Liu, Yuanyuan An, Yubin Wang
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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