Publication | Open Access
Reductive Cyclization of Unactivated Alkyl Chlorides with Tethered Alkenes under Visible‐Light Photoredox Catalysis
15
Citations
53
References
2019
Year
Tethered AlkenesEngineeringSynthetic PhotochemistryOrganic ChemistryChemistryVisible‐light Photoredox ReductionChemical EngineeringPhotoredox ProcessPhotocatalysisOrganometallic CatalysisPhotochemistryDiversity-oriented SynthesisReductive CyclizationCatalysisMetallaphotoredox MethodologyChemical InertnessVisible‐light Photoredox CatalysisAlkene MetathesisNatural Sciences
Abstract The chemical inertness of abundant and commercially available alkyl chlorides precludes their widespread use as reactants in chemical transformations. Presented in this work is a metallaphotoredox methodology to achieve the catalytic intramolecular reductive cyclization of unactivated alkyl chlorides with tethered alkenes. The cleavage of strong C(sp 3 )−Cl bonds is mediated by a highly nucleophilic low‐valent cobalt or nickel intermediate generated by visible‐light photoredox reduction employing a copper photosensitizer. The high basicity and multidentate nature of the ligands are key to obtaining efficient metal catalysts for the functionalization of unactivated alkyl chlorides.
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