Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis

Hong Jie Miao; Jin Hua Zhang; Shuai Liu; Wen Hong Wang; Xu Yang; Xin Hua Duan; Li Na Guo

doi:10.1021/acs.orglett.3c01809

Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis

Hong Jie Miao
, Jin Hua Zhang
, Shuai Liu
, Wen Hong Wang
, Xu Yang
, Xin Hua Duan
, Li Na Guo

Xi'an Jiaotong University

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

22 Scopus citations

Abstract

A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF₃ functional groups. Remarkably, incorporation of the NH₂ group onto the 1,3-enyne moiety enabled further cyclization to give a unique scaffold containing a lactone and an indole moiety.

Original language	English
Pages (from-to)	5563-5568
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	30
DOIs	https://doi.org/10.1021/acs.orglett.3c01809
State	Published - 4 Aug 2023

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10.1021/acs.orglett.3c01809

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title = "Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis",

abstract = "A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation of the NH2 group onto the 1,3-enyne moiety enabled further cyclization to give a unique scaffold containing a lactone and an indole moiety.",

author = "Miao, \{Hong Jie\} and Zhang, \{Jin Hua\} and Shuai Liu and Wang, \{Wen Hong\} and Xu Yang and Duan, \{Xin Hua\} and Guo, \{Li Na\}",

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year = "2023",

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doi = "10.1021/acs.orglett.3c01809",

language = "英语",

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T1 - Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis

AU - Miao, Hong Jie

AU - Zhang, Jin Hua

AU - Liu, Shuai

AU - Wang, Wen Hong

AU - Yang, Xu

AU - Duan, Xin Hua

AU - Guo, Li Na

PY - 2023/8/4

Y1 - 2023/8/4

N2 - A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation of the NH2 group onto the 1,3-enyne moiety enabled further cyclization to give a unique scaffold containing a lactone and an indole moiety.

AB - A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation of the NH2 group onto the 1,3-enyne moiety enabled further cyclization to give a unique scaffold containing a lactone and an indole moiety.

UR - https://www.scopus.com/pages/publications/85166482765

U2 - 10.1021/acs.orglett.3c01809

DO - 10.1021/acs.orglett.3c01809

M3 - 文章

C2 - 37477589

AN - SCOPUS:85166482765

SN - 1523-7060

VL - 25

SP - 5563

EP - 5568

JO - Organic Letters

JF - Organic Letters

IS - 30

ER -

Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis

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