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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Cascade double isocyanide insertion and C-N coupling of 2-iodo-2'-isocyano-1,1'-biphenyls
Hongwei Sun1, Shi Tang, Dengke Li
1State Key Laboratory of Respiratory Disease, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, P. R. China. huang_jinbo@gibh.ac.cn zhu_qiang@gibh.ac.cn.
Abstract:
A palladium-catalyzed double isocyanide insertion using 2-iodo-2'-isocyano-1,1'-biphenyls followed by copper-catalyzed intramolecular C-N coupling, delivering a unique heterocyclic structure containing both phenanthridine and carbazole scaffolds, has been developed. In this cascade process, four chemical bonds, including two C-C, one C-O, and one C-N bonds are formed consecutively without isolating an intermediate. The strategy of using a functionalized isocyanide in double insertion provides a quick approach for constructing heterocyclic systems with high bond-forming efficiency.
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