Organic Letters
Organic Letters
4 years ago

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

Silver-Catalyzed Tandem CC Bond Hydroazidation/Radical Addition/Cyclization of Biphenyl Acetylene: One-Pot Synthesis of 6-Methyl Sulfonylated Phenanthridines
Yongquan Ning, Paramasivam Sivaguru, Xihe Bi, Jiawei Tang, Giuseppe Zanoni
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01771

DOI: 10.1021/acs.orglett.7b01771

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