Room-temperature palladium-catalyzed direct 2-alkenylation of azole derivatives with alkenyl bromides

[Display omitted] •Direct 2-alkenylation of azoles with aryl bromides at room-temperature.•Palladium/NiXantphos-base catalysis enables this process.•Deprotonative cross-coupling process (DCCP) in the alkenylation.•Structural diverse 2-alkenylazoles were prepared. Pd-catalyzed direct C2-alkenylation...

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Bibliographic Details
Published in:Tetrahedron letters 2019-01, Vol.60 (1), p.68-71
Main Authors: Yao, Yun-Xin, Fang, Dong-Mei, Gao, Feng, Liang, Xiao-Xia
Format: Article
Language:English
Subjects:
Alkenylation
Azole
NiXantphos
Palladium-catalysis
Room-temperature
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Summary:[Display omitted] •Direct 2-alkenylation of azoles with aryl bromides at room-temperature.•Palladium/NiXantphos-base catalysis enables this process.•Deprotonative cross-coupling process (DCCP) in the alkenylation.•Structural diverse 2-alkenylazoles were prepared. Pd-catalyzed direct C2-alkenylation of azole derivatives proceeds efficiently under mild conditions, and the reaction of substituted benzoxazoles, oxazole and benzothiazole occurred even at room temperature. The substrate scope of the reaction was turned out to include mono-, di- and trisubstituted alkenyl bromides. To validate the scalability of this method, 5-Methyl-2-(prop-1-en-2-yl)benzoxazole (3c) was prepared on one-gram scale at room temperature.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.11.058