Copper(I)-catalyzed cyanoperfluoroalkylation of alkynes

Muhammad Israr; Haigen Xiong; Yajun Li; Hongli Bao

doi:10.1021/acs.orglett.9b02648

Copper(I)-catalyzed cyanoperfluoroalkylation of alkynes

Muhammad Israr, Haigen Xiong, Yajun Li, Hongli Bao^*

^*Corresponding author for this work

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

25 Scopus citations

Abstract

A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed. The perfluoroalkylated cyanoalkenes that are produced can be readily transformed into useful fluoroalkylated derivatives.

Original language	English
Pages (from-to)	7078-7083
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.9b02648
State	Published - 6 Sep 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2019 American Chemical Society.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Copper(I)-catalyzed cyanoperfluoroalkylation of alkynes",

abstract = "A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed. The perfluoroalkylated cyanoalkenes that are produced can be readily transformed into useful fluoroalkylated derivatives.",

author = "Muhammad Israr and Haigen Xiong and Yajun Li and Hongli Bao",

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doi = "10.1021/acs.orglett.9b02648",

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AU - Xiong, Haigen

AU - Li, Yajun

AU - Bao, Hongli

PY - 2019/9/6

Y1 - 2019/9/6

N2 - A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed. The perfluoroalkylated cyanoalkenes that are produced can be readily transformed into useful fluoroalkylated derivatives.

AB - A highly chemoselective and regioselective copper-catalyzed radical cyanoperfluoroalkylation of alkynes is described. This three-component reaction directly uses commercially available alkynes, perfluoroalkyl iodides, and trimethylsilyl cyanide as the reaction partners and delivers a variety of perfluoroalkylated cyanoalkenes in good yields. Broad substrate scope and good functional group tolerance are observed. The perfluoroalkylated cyanoalkenes that are produced can be readily transformed into useful fluoroalkylated derivatives.

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ER -

Copper(I)-catalyzed cyanoperfluoroalkylation of alkynes

Abstract

Bibliographical note

ASJC Scopus subject areas

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