Borane-catalyzed cascade Friedel–Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines |
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| Authors: | Bei-Bei Zhang Shuo Peng Feiyi Wang Cuifen Lu Junqi Nie Zuxing Chen Guichun Yang Chao Ma |
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| Institution: | Hubei Collaborative Innovation Centre for Advanced Organic Chemical Materials, College of Chemistry and Chemical Engineering, Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Hubei University, Wuhan 430062 P. R. China, |
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| Abstract: | An unprecedented redox-neutral annulation reaction of tertiary anilines with electron-deficient alkynes was developed that proceeds through a cascade Friedel–Crafts alkylation/1,5]-hydride transfer/Mannich cyclization sequence. Under B(C6F5)3 catalysis, a range of functionalized 1,2,3,4-tetrahydroquinolines were facilely constructed in moderate to good yields with exclusive 3,4-anti-stereochemistry. The commercial availability of the catalyst and the high atom and step economy of the procedure, together with metal-free and external oxidant-free conditions, make this an attractive method in organic synthesis.We report a redox-neutral annulation reaction of tertiary amines with electron-deficient alkynes under metal-free and oxidant-free conditions. |
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