Iron-Catalyzed Carboiodination of Alkynes

Weili Deng; Yajun Li; You-Gui Li; Hongli Bao

doi:10.1055/s-0037-1609448

Synthesis, Table of Contents

Synthesis 2018; 50(15): 2974-2980
DOI: 10.1055/s-0037-1609448

special topic

Iron-Catalyzed Carboiodination of Alkynes

Weili Deng

^aSchool of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, P. R. of China Email: liyg@hfut.edu.cn

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

,

Yajun Li

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

,

You-Gui Li*

^aSchool of Chemistry and Chemical Engineering, Hefei University of Technology, 193 Tunxi Road, Hefei 230009, P. R. of China Email: liyg@hfut.edu.cn

,

Hongli Bao *

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, P. R. of China Email: hlbao@fjirsm.ac.cn

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Abstract

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Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis

Abstract

An iron-catalyzed carboiodination of alkynes with alkyl iodides at room temperature was developed. This method could provide synthetically useful vinyl iodides with general alkyl chains, fluoroalkyl group, ester, and cyano group. Conjugated alkynes or unconjugated alkynes were both suitable for this transformation. A radical pathway was proposed for the mechanism and acetyl tert-butyl peroxide was selected as the radical initiator. Alkenes could also be applied to this chemistry and produce more complex alkyl iodides.

Key words

iron catalysis - radical - alkyl iodides - alkynes - carboiodination

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References

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