The Journal of Organic Chemistry · 2019 · 42 citations · 38 references
Natural SciencesChemistryOrganic ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisPhotochemical SynthesisPhotochemistryRetrosynthetic AnalysisEnyne CyclizationPhotochemical CycloadditionPhotocyclization ReactionsPyrrolidine SynthesisRadical CyclizationRing-forming ReactionsStereoselective Synthesis
Described herein is a visible-light-driven chlorotrifluoromethylative and chlorotrichloromethylative cyclization reaction to synthesize chlorotrifluoromethylated and chlorotrichloromethylated cyclic compounds. Visible-light photochemistry was utilized to generate trifluoromethyl and trichloromethyl radicals and trigger radical addition/cyclization/chlorination sequences. The use of terminal alkene-derived enynes enables the regioselective and stereoselective synthesis of chlorotrifluoromethylated and chlorotrichloromethylated pyrrolidines, piperidines, and cyclopentanes.
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Photoredox Catalysis in Organic Chemistry
Megan H. Shaw, Jack Twilton, David W. C. MacMillan · The Journal of Organic Chemistry · 2016 · 3.1K citations · Full text