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Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes

Zuxiao Zhang,Xiaojun Tang,Charles S. Thomoson,William R. Dolbier

Chemistry

Nucleophile

Catalysis

2015

A photoredox catalyzed aminodifluoromethylation of unactivated alkenes has been developed in which HCF2SO2Cl is used as the HCF2 radical source. Sulfonamides were active nucleophiles in the final step of a tandem addition/oxidation/cyclization process to form pyrrolidines, and esters were found to cyclize to form lactones. Thus, a variety of pyrrolidines and lactones were obtained in moderate to excellent yield. In order for the cyclization reactions to be efficient, a combination of a copper catalyst (Cu(dap)2Cl) and silver carbonate was crucial to suppressing a competing chloro, difluoroalkylation process.

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“Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes” is a paper by Zuxiao Zhang Xiaojun Tang Charles S. Thomoson William R. Dolbier published in 2015. It has an Open Access status of “closed”. You can read and download a PDF Full Text of this paper here.