Trifluoromethanesulfonic Acid Catalyzed Synergetic Oxidative/[3+2] Cyclization of Quinones with Olefins†
Lingkui Meng
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorGuanghui Zhang
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorDr. Chao Liu
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorKun Wu
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorCorresponding Author
Prof. Aiwen Lei
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, 430071 (P.R. China)
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/Search for more papers by this authorLingkui Meng
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorGuanghui Zhang
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorDr. Chao Liu
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorKun Wu
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Search for more papers by this authorCorresponding Author
Prof. Aiwen Lei
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery (Wuhan University), Ministry of Education, and Wuhan University School of Pharmaceutical Sciences, Wuhan, 430071 (P.R. China)
College of Chemistry and Molecular Science, Wuhan University, Wuhan 430072 (P.R. China) http://aiwenlei.whu.edu.cn/Main_Website/Search for more papers by this authorThis work was supported by the 973 Program (2012CB725302), the National Natural Science Foundation of China (21025206 and 21272180), the Research Fund for the Doctoral Program of Higher Education of China (20120141130002). and the China Postdoctoral Science Foundation funded project (2012M521458). We are also grateful for support from the Program for Changjiang Scholars and Innovative Research Team in University (IRT1030).
Graphical Abstract
The proton did it! Tetrahydrobenzodifurans have been synthesized through the trifluoromethanesulfonic acid (HOTf) catalyzed direct oxidative CH functionalization of benzoquinone with olefins. A variety of substituents were found to be tolerated, and a synergetic oxidative/[3+2] cyclization mechanism was proposed based on the experimental results.
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