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Transition‐Metal‐Catalyst‐Free Cross‐Coupling Reaction of Secondary Propargylic Acetates with Alkenyl‐ and Arylboronic Acids
Author(s) -
Ueda Mitsuhiro,
Nakakoji Daiki,
Morisaki Takahiro,
Ryu Ilhyong
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701450
Subject(s) - chemistry , catalysis , transition metal , base (topology) , reaction conditions , coupling reaction , organic chemistry , metal , combinatorial chemistry , medicinal chemistry , mathematical analysis , mathematics
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.