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

Bu Qing Cheng; Si Xuan Zhang; Yan Ying Cui; Xue Qiang Chu; Weidong Rao; Haiyan Xu; Guo Zhi Han; Zhi Liang Shen

doi:10.1021/acs.orglett.0c01828

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

Bu Qing Cheng, Si Xuan Zhang, Yan Ying Cui, Xue Qiang Chu, Weidong Rao, Haiyan Xu, Guo Zhi Han, Zhi Liang Shen

School of Chemistry and Moleculai Engineering

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	5456-5461
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.0c01828
State	Published - 17 Jul 2020

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

abstract = "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.",

author = "Cheng, {Bu Qing} and Zhang, {Si Xuan} and Cui, {Yan Ying} and Chu, {Xue Qiang} and Weidong Rao and Haiyan Xu and Han, {Guo Zhi} and Shen, {Zhi Liang}",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

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doi = "10.1021/acs.orglett.0c01828",

language = "英语",

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T1 - Copper(II)-Mediated Ring Opening/Alkynylation of Tertiary Cyclopropanols by Using Nonmodified Terminal Alkynes

AU - Cheng, Bu Qing

AU - Zhang, Si Xuan

AU - Cui, Yan Ying

AU - Chu, Xue Qiang

AU - Rao, Weidong

AU - Xu, Haiyan

AU - Han, Guo Zhi

AU - Shen, Zhi Liang

PY - 2020/7/17

Y1 - 2020/7/17

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85087679088&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01828

DO - 10.1021/acs.orglett.0c01828

M3 - 文章

C2 - 32603133

AN - SCOPUS:85087679088

SN - 1523-7060

VL - 22

SP - 5456

EP - 5461

JO - Organic Letters

JF - Organic Letters

IS - 14

ER -

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

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