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

Bu-Qing Cheng,^a Si-Xuan Zhang,^a Yan-Ying Cui,^a Xue-Qiang Chu,^a Weidong Rao,^b Haiyan Xu,^c Guo-Zhi Han,*^,a and Zhi-Liang Shen*^,a

^a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, China

^b Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China

^c School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212003, China

Abstract: Copper(II)-mediated ring opening/alkynylation of cyclopropanol by employing cheap 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.

Organic Letters 2020, 22, 5456-5461. (Impact factor: 6.091)

论文链接：https://pubs.acs.org/doi/10.1021/acs.orglett.0c01828