Concise Report
Copper-Mediated Selective Multiple Inert Chemical Bonds Cleavage for Cyanation of Indoles via Tandem Carbon and Nitrogen Atom Transfer
Shimin Xie,
Fangfang Cai,
Lixin Liu,
Lebin Su,
Jianyu Dong,
Yongbo Zhou,
Shimin Xie
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorFangfang Cai
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorLixin Liu
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorLebin Su
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorCorresponding Author
Jianyu Dong
School of Physics and Chemistry, Hunan First Normal University, Changsha, Hunan, 410205 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yongbo Zhou
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
E-mail: [email protected]; [email protected]Search for more papers by this authorShimin Xie,
Fangfang Cai,
Lixin Liu,
Lebin Su,
Jianyu Dong,
Yongbo Zhou,
Shimin Xie
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorFangfang Cai
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorLixin Liu
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorLebin Su
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
Search for more papers by this authorCorresponding Author
Jianyu Dong
School of Physics and Chemistry, Hunan First Normal University, Changsha, Hunan, 410205 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Yongbo Zhou
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, Hunan, 410082 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
The activation of inert chemical bonds is an exciting area of research in chemistry because it enables the direct utilization of readily available starting materials and promotes atom- and step-economic synthesis. Undoubtedly, selectively activating and transforming multiple inert chemical bonds is an even more intriguing and demanding task in synthetic chemistry. However, due to its inherent complexity and extreme challenges, this endeavour is rarely accomplished. We report a copper-mediated complete cleavage and selective transformation of multiple inert chemical bonds of three easily available feedstocks, i.e., a sp2C—H bond in indoles, three sp3C—H bonds and one C—N bond in a methyl carbon atom in TMEDA, and the C≡N triple bond in CH3CN. This reaction proceeds via tandem carbon and nitrogen atom transfer, and allows for the direct and efficient cyanation of indoles, presenting a simple and direct alternative for synthesizing 3-cyanoindoles.
Supporting Information
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Appendix S1: Supporting Information |
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