title: Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: Zuxiao
authors.initials: Z
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: Xiaojun
authors.initials: X
authors.lastname: Tang
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: Charles S
authors.initials: CS
authors.lastname: Thomoson
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, United States.
authors.forename: William R
authors.initials: WR
authors.lastname: Dolbier
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003300:Copper; D003500:Cyclization; D008744:Methylamines / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000737:chemistry*; D018030:Silver Compounds / Q000737:chemistry*
chemical_list: D000475:Alkenes; D002254:Carbonates; D008744:Methylamines; D011759:Pyrrolidines; D018030:Silver Compounds; D003300:Copper; C033260:silver carbonate