Visible-Light Reductive Cyclization of Nonactivated Alkyl Chlorides
SYNLETT(2019)
Abstract
Nonactivated alkyl chlorides are readily available and bench-stable feedstocks; however, they exhibit an inherent chemical inertness, in part, due to their large negative reduction potentials, which have precluded their widespread use as radical precursors in visible-light photocatalysis. Herein, we highlight some recent strategies for activating challenging organic halides under light irradiation, with special emphasis in C(sp(3))-halide bonds. In this line, a brief summary of the reactivity of Vitamin B-12, F-430 cofactor and derivatives is required to comprehend the chemistry behind our developed Cu/M (M = Co, Ni) dual catalytic system. Catalyst design has been key for developing a mild and general photoredox methodology for the intramolecular reductive cyclization of nonactivated 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.
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Key words
nonactivated alkyl chlorides,visible-light,photoredox catalysis,cyclizations,vitamin B-12,cobaloximes
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