Transition‐Metal‐Catalyst‐Free Cross‐Coupling Reaction of Secondary Propargylic Acetates with Alkenyl‐ and Arylboronic Acids

A cross‐coupling reaction between secondary propargylic acetates and alkenylboronic acids proceeded to give 1,4‐enynes in good yields without addition of transition metal catalyst and base. This simple protocol was also applicable to arylboronic acids, which gave 3‐arylated alkynes in good yields. T...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-12, Vol.2017 (47), p.7040-7045
Main Authors: Ueda, Mitsuhiro, Nakakoji, Daiki, Morisaki, Takahiro, Ryu, Ilhyong
Format: Article
Language:English
Subjects:
Acetates
Acids
Alkenylboronic acids
Alkynes
Arylboronic acids
Catalysis
Catalysts
Catalyst‐free reactions
Chemical industry
Chemical reactions
Cross coupling
Propargylic acetates
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Summary:A cross‐coupling reaction between secondary propargylic acetates and alkenylboronic acids proceeded to give 1,4‐enynes in good yields without addition of transition metal catalyst and base. This simple protocol was also applicable to arylboronic acids, which gave 3‐arylated alkynes in good yields. The observed induction period suggested that the reaction of propargylic acetates and organoboronic acids was affected by the in‐situ generated AcOH as a catalyst, which was confirmed by a separate experiment. A cross‐coupling reaction between secondary propargylic acetates and alkenylboronic acids proceeded to give 1,4‐enynes in good yields without addition of transition metal catalyst and base. This simple protocol was also applicable to arylboronic acids, which gave 3‐arylated alkynes in good yields.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201701450