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DOI: 10.1055/s-0037-1611878
Visible-Light Reductive Cyclization of Nonactivated Alkyl Chlorides
We acknowledge the financial support from the ICIQ Foundation and MINECO (CTQ2016-80038-R) to J. Ll.-F.Publication History
Received: 26 May 2019
Accepted after revision: 11 June 2019
Publication Date:
17 July 2019 (online)
![](https://www.thieme-connect.de/media/synlett/201913/lookinside/thumbnails/st-2019-p0291-sp_10-1055_s-0037-1611878-1.jpg)
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.
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