A Metal-Free Approach for Brønsted Acid Promoted C–H Alkyl­ation of Heteroarenes with Alkyl Peroxides

Yuehua Zeng; Bo Qian; Yajun Li; Hongli Bao

doi:10.1055/s-0037-1609965

Synthesis, Table of Contents

Synthesis 2018; 50(16): 3250-3256
DOI: 10.1055/s-0037-1609965

paper

A Metal-Free Approach for Brønsted Acid Promoted C–H Alkylation of Heteroarenes with Alkyl Peroxides

Yuehua Zeng

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute ofResearch on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People’s Republic of China Email: hlbao@fjirsm.ac.cn Email: qianbo@fjirsm.ac.cn

^bCollege of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350108, People’s Republic of China

,

Bo Qian*

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute ofResearch on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People’s Republic of China Email: hlbao@fjirsm.ac.cn Email: qianbo@fjirsm.ac.cn

,

Yajun Li

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute ofResearch on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People’s Republic of China Email: hlbao@fjirsm.ac.cn Email: qianbo@fjirsm.ac.cn

,

Hongli Bao *

^aKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute ofResearch on the Structure of Matter, University of Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian 350002, People’s Republic of China Email: hlbao@fjirsm.ac.cn Email: qianbo@fjirsm.ac.cn

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Abstract

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Abstract

A metal-free protocol for Minisci C–H alkylation of heteroarenes using alkyl peroxides as the alkylating reagents and internal oxidants simultaneously under promotion of Brønsted acid has been demonstrated. A series of alkyl substituted heteroarenes were readily prepared by the C–H alkylation in moderate to good yields. A possible pathway involving the addition of alkyl radical to heterocycle followed by rearomatization is described.

Key words

metal-free conditions - Brønsted acid - C–H alkylation - heteroarenes - alkyl peroxides

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References

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Supplementary Material

Supporting Information

A Metal-Free Approach for Brønsted Acid Promoted C–H Alkyl­ation of Heteroarenes with Alkyl Peroxides

A Metal-Free Approach for Brønsted Acid Promoted C–H Alkylation of Heteroarenes with Alkyl Peroxides