Photoinduced inverse Sonogashira coupling reaction

Lizhu Zhang; Cunbo Wei; Jiawen Wu; Dan Liu; Yinchao Yao; Zhuo Chen; Jianxun Liu; Chang Jiang Yao; Dinghua Li; Rongjie Yang; Zhonghua Xia

doi:10.1039/d2sc01933g

Photoinduced inverse Sonogashira coupling reaction

Lizhu Zhang, Cunbo Wei, Jiawen Wu, Dan Liu, Yinchao Yao, Zhuo Chen, Jianxun Liu, Chang Jiang Yao, Dinghua Li, Rongjie Yang, Zhonghua Xia^*

^*Corresponding author for this work

Beijing Institute of Technology

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

18 Citations (Scopus)

Abstract

Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an “alkynyl radical synthetic equivalent”, reacting with a series of C(sp²)-H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.

Original language	English
Pages (from-to)	7475-7481
Number of pages	7
Journal	Chemical Science
Volume	13
Issue number	25
DOIs	https://doi.org/10.1039/d2sc01933g
Publication status	Published - 30 May 2022

Access to Document

10.1039/d2sc01933g

Cite this

@article{44ed482870b44a969f92b9b003e38d3a,

title = "Photoinduced inverse Sonogashira coupling reaction",

abstract = "Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an “alkynyl radical synthetic equivalent”, reacting with a series of C(sp2)-H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.",

author = "Lizhu Zhang and Cunbo Wei and Jiawen Wu and Dan Liu and Yinchao Yao and Zhuo Chen and Jianxun Liu and Yao, {Chang Jiang} and Dinghua Li and Rongjie Yang and Zhonghua Xia",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = may,

day = "30",

doi = "10.1039/d2sc01933g",

language = "English",

volume = "13",

pages = "7475--7481",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "25",

}

TY - JOUR

T1 - Photoinduced inverse Sonogashira coupling reaction

AU - Zhang, Lizhu

AU - Wei, Cunbo

AU - Wu, Jiawen

AU - Liu, Dan

AU - Yao, Yinchao

AU - Chen, Zhuo

AU - Liu, Jianxun

AU - Yao, Chang Jiang

AU - Li, Dinghua

AU - Yang, Rongjie

AU - Xia, Zhonghua

PY - 2022/5/30

Y1 - 2022/5/30

N2 - Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an “alkynyl radical synthetic equivalent”, reacting with a series of C(sp2)-H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.

AB - Alkynes are widely used in chemistry, medicine and materials science. Here we demonstrate a transition-metal and photocatalyst-free inverse Sonogashira coupling reaction between iodoalkynes and (hetero)arenes or alkenes under visible-light irradiation. Mechanistic and computational studies suggest that iodoalkynes can be directly activated by visible light irradiation, and an excited state iodoalkyne acted as an “alkynyl radical synthetic equivalent”, reacting with a series of C(sp2)-H bonds for coupling products. This work should open new windows in radical chemistry and alkynylation method.

UR - http://www.scopus.com/inward/record.url?scp=85131750576&partnerID=8YFLogxK

U2 - 10.1039/d2sc01933g

DO - 10.1039/d2sc01933g

M3 - Article

AN - SCOPUS:85131750576

SN - 2041-6520

VL - 13

SP - 7475

EP - 7481

JO - Chemical Science

JF - Chemical Science

IS - 25

ER -

Photoinduced inverse Sonogashira coupling reaction

Abstract

Access to Document

Other files and links

Fingerprint

Cite this