Visible-Light Reductive Cyclization of Nonactivated Alkyl Chlorides

Miguel Claros; Alicia Casitas; Julio Lloret-Fillol

doi:10.1055/s-0037-1611878

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(13): 1496-1507
DOI: 10.1055/s-0037-1611878

synpacts

Visible-Light Reductive Cyclization of Nonactivated Alkyl Chlorides

Miguel Claros

^aInstitute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Avda. Països Catalans, 16, 43007, Tarragona, Spain eMail: jlloret@iciq.es

^bUniversity Rovira i Virgili (URV) department of physical and inorganic chemistry, C/Marcel·lí Domingo, 43007 Tarragona, Catalonia, Spain

,

Alicia Casitas∗

^cInstitut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona, Campus de Montilivi, 17003 Girona, Catalonia, Spain eMail: alicia.casitas@udg.edu

,

Julio Lloret-Fillol∗

^aInstitute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Avda. Països Catalans, 16, 43007, Tarragona, Spain eMail: jlloret@iciq.es

^dCatalan Institution for Research and Advanced Studies (ICREA),Passeig Lluïs Companys, 23, 08010, Barcelona, Spain

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Abstract

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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(sp³)–halide bonds. In this line, a brief summary of the reactivity of Vitamin B₁₂, F₄₃₀ 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(sp³)–Cl bonds is mediated by a highly nucleophilic low-valent cobalt or nickel intermediate generated by visible-light photoredox reduction employing a copper photosensitizer.

Key words

nonactivated alkyl chlorides - visible-light - photoredox catalysis - cyclizations - vitamin B₁₂ - cobaloximes

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Referenzen

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