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Silver-Catalyzed Tandem CC Bond Hydroazidation/Radical Addition/Cyclization of Biphenyl Acetylene: One-Pot Synthesis of 6‑Methyl Sulfonylated Phenanthridines

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posted on 2017-07-24, 04:29 authored by Jiawei Tang, Paramasivam Sivaguru, Yongquan Ning, Giuseppe Zanoni, Xihe Bi
A silver-catalyzed tandem carbon–carbon triple bond hydroazidation, radical addition, and cyclization of biphenyl acetylene is described under mild conditions, leading to the formation of 6-methyl sulfonylated phenanthridines in good yields. In this novel cascade reaction, most of the atoms are incorporated into the product without cleavage of the CC bond. Mechanistic studies suggest the reaction should proceed through an iminyl radical reactive intermediate.

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