Copper(II)-Mediated Ring Opening/Alkynylation of Tertiary Cyclopropanols by Using Nonmodified Terminal Alkynes

The copper­(II)-mediated ring opening/alkynylation of cyclopropanol by employing inexpensive and commercially available terminal alkyne is developed. The reactions proceeded efficiently to afford synthetically useful alk-4-yn-1-ones in moderate to good yields with good functional group tolerance. Co...

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Veröffentlicht in:Organic letters 2020-07, Vol.22 (14), p.5456-5461
Hauptverfasser: Cheng, Bu-Qing, Zhang, Si-Xuan, Cui, Yan-Ying, Chu, Xue-Qiang, Rao, Weidong, Xu, Haiyan, Han, Guo-Zhi, Shen, Zhi-Liang
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Sprache:eng
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Zusammenfassung:The copper­(II)-mediated ring opening/alkynylation of cyclopropanol by employing inexpensive and commercially available terminal alkyne is developed. The reactions proceeded efficiently to afford synthetically useful alk-4-yn-1-ones in moderate to good yields with good functional group tolerance. Control experiments showed that the reaction presumably proceeds via the formation of intermediates of copper homoenolate and/or alkynylcopper species.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01828