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

Bu-Qing Cheng,^aSi-Xuan Zhang,^aYan-Ying Cui,^aXue-Qiang Chu,^aWeidong Rao,^bHaiyan Xu,^cGuo-Zhi Han,*^,aand Zhi-Liang Shen*^,a

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

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

^cSchool 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 Letters2020,22, 5456-5461.(Impact factor:6.091)

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