Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes

Photoredox-Catalyzed Intramolecular Aminodifluoromethylation of Unactivated Alkenes

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 c...

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Veröffentlicht in:Organic letters 2015-07, Vol.17 (14), p.3528-3531
Hauptverfasser: Zhang, Zuxiao, Tang, Xiaojun, Thomoson, Charles S, Dolbier, Jr, William R
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
Carbonates - chemistry
Catalysis
Copper
Cyclization
Methylamines - chemistry
Methylation
Molecular Structure
Oxidation-Reduction
Pyrrolidines - chemistry
Silver Compounds - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01616