Controllable chemoselectivity in the coupling of bromoalkynes with alcohols under visible-light irradiation without additives: synthesis of propargyl alcohols and α-ketoesters

The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N 2 or O 2 ). A N 2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O 2 atmosphere results in the generat...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-07, Vol.55 (58), p.8438-8441
Main Authors: Ni, Ke, Meng, Ling-Guo, Ruan, Hongjie, Wang, Lei
Format: Article
Language:English
Subjects:
Additives
Alcohol
Alcohols
Chemical reactions
Coupling
Light irradiation
Stability
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Summary:The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere (N 2 or O 2 ). A N 2 atmosphere favours propargyl alcohols via a direct C-C coupling process, whereas an O 2 atmosphere results in the generation of α-ketoesters through the oxidative C&z.tbd;C/C-O coupling pathway. The chemoselectivity of visible-light-induced coupling reactions of bromoalkynes with alcohols can be controlled by simple changes to the reaction atmosphere.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc04090k