Download PDF
Synthesis 2018; 50(16): 3250-3256
DOI: 10.1055/s-0037-1609965
paper
© Georg Thieme Verlag Stuttgart · New York

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

Yuehua Zeng
a   Key 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
b   College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian 350108, People’s Republic of China
,
Bo Qian*
a   Key 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
a   Key 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  *
a   Key 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
› Author AffiliationsWe thank NSFC (Grant Nos. 21502191 and 21672213), Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB20000000), The 100 Talents Program, ‘The 1000 Youth Talents Program’, Natural Science Foundation of Fujian Province (Grant No. 2016J01081) and Haixi Institute of CAS (CXZX-2017-P01) for financial support.
Further Information

Publication History

Received: 28 March 2018

Accepted after revision: 16 April 2018

Publication Date:
29 May 2018 (online)

   Buy Article Permissions and Reprints All articles of this category


Zoom Image

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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609965.
  • Supporting Information