Decarboxylation of β-boryl NHPI esters enables radical 1,2-boron shift for the assembly of versatile organoborons

In recent years, numerous 1,2-R shift (R = aliphatic or aryl) based on tetracoordinate boron species have been well investigated. In the contrary, the corresponding radical migrations, especially 1,2-boryl radical shift for the construction of organoborons is still in its infancy. Given the paucity...

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Published in:Nature communications 2023-09, Vol.14 (1), p.5693-11, Article 5693
Main Authors: Guo, Yu, Wang, Xiaosha, Li, Chengbo, Su, Jianke, Xu, Jian, Song, Qiuling
Format: Article
Language:English
Subjects:
140/131
140/58
639/638/439/890
639/638/549/933
639/638/77/890
Boron
Chemical reactions
Coupling (molecular)
Cross coupling
Decarboxylation
Esters
Humanities and Social Sciences
Light effects
multidisciplinary
Science
Science (multidisciplinary)
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Summary:In recent years, numerous 1,2-R shift (R = aliphatic or aryl) based on tetracoordinate boron species have been well investigated. In the contrary, the corresponding radical migrations, especially 1,2-boryl radical shift for the construction of organoborons is still in its infancy. Given the paucity and significance of such strategies in boron chemistry, it is urgent to develop other efficient and alternative synthetic protocols to enrich these underdeveloped radical 1,2-boron migrations, before their fundamental potential applications could be fully explored at will. Herein, we have demonstrated a visible-light-induced photoredox neutral decarboxylative radical cross-coupling reaction, which undergoes a radical 1,2-boron shift to give a translocated C-radical for further capture of versatile radical acceptors. The mild reaction conditions, good functional-group tolerance, and broad β-boryl NHPI esters scope as well as versatile radical acceptors make this protocol applicable in modification of bioactive molecules. It can be expected that this methodology will be a very useful tool and an alternative strategy for the construction of primary organoborons via a novel radical 1,2-boron shift mode. The 1,2 migration reaction on tetracoordinate boron species have been well investigated but less work looked on 1,2-boryl radical shift for the construction of organoborons. Here, the authors demonstrate a visible-light-induced photoredox neutral decarboxylative radical cross-coupling reaction, which undergoes a radical 1,2-boron shift to give a translocated C-radical for further capture of versatile radical acceptors
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-023-41254-1