Metal-free tandem carbene N–H insertions and C–C bond cleavages |
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| Authors: | Pu Chen Jiang Nan Yan Hu Yifan Kang Bo Wang Yangmin Ma Michal Szostak |
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| Institution: | Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi''an 710021 China.; Department of Chemistry, Rutgers University, 73 Warren Street, Newark New Jersey 07102 USA |
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| Abstract: | A metal-free C–H 5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. Compared to the simple N–H insertion manipulation of diazo, this method elegantly accomplishes a tandem N–H insertion/SEAr/C–C cleavage/aromatization reaction, and the synthetic utility of this new transformation is exemplified by the succinct syntheses of trisphaeridine and bicolorine alkaloids.A metal-free C–H 5 + 1] annulation reaction of 2-arylanilines with diazo compounds has been achieved, giving rise to two types of prevalent phenanthridines via highly selective C–C cleavage. |
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