Shining Visible Light on Vinyl Halides: Expanding the Horizons of Photocatalysis

Accounts of Chemical Research
Santosh K PagireOliver Reiser

Abstract

ConspectusOver the past decade, photoredox catalysis has blossomed as a powerful methodology because of its wide applicability in sustainable free-radical-mediated processes, in which light is used as a cleaner energy source to alter the redox properties of organic molecules and to drive unique chemical transformations. Numerous examples of highly selective C-C and C-heteroatom bond formation processes have been achieved this way in an efficient and waste-reducing way. Therein, the activation of widely available organic halides via single-electron reduction has been broadly applied for organic synthesis. However, in comparison with alkyl and aryl halides, the analogous utilization of vinyl halides is less developed, most likely as a consequence of the highly unstable vinyl radicals generated as intermediates along with their strong tendency to abstract hydrogen atoms from a suitable source (e.g., the solvent), resulting in a synthetically less useful reduction.Nevertheless, during the last years, a number of photocatalytic processes involving vinyl halides have been developed, featuring the generation of vinyl radicals, diradicals, or radical cations as the key transient species. Moreover, photoredox processes in which a radica...Continue Reading

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Citations

May 19, 2021·Nature Communications·Yanjun LiLei Gong
May 28, 2021·The Journal of Organic Chemistry·Yunlong LiZhengkun Yu
Jun 13, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Zach Medcalf, Kevin D Moeller
Jul 3, 2020·Journal of the American Chemical Society·Yonghoon MoonSungwoo Hong

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