Visible Light Mediated Reductive Cleavage of C-O Bonds Accessing α-Substituted Aryl Ketones

Elisabeth Speckmeier, Clément Padié and Kirsten Zeitler*

*Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany, Email: kzeitleruni-leipzig.de

E. Speckmeier, C. Padié, K. Zeitler, Org. Lett., 2015, 17, 4818-4821.

DOI: 10.1021/acs.orglett.5b02378

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Abstract

Acetates of benzoin derivatives can be effectively reduced using catalytic amounts of [Ru(bpy)₃]Cl₂ as photoredox catalyst in combination with Hantzsch ester and triethylamine as a sacrificial electron donor. This mild and operationally simple method is applicable to a broad range of substrates providing deoxygenated counterparts in good yields.

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Note

The protocol tolerates aryl halides, including Ar-I bonds without their reductive cleavage (referenced as footnote 27 within the paper).

Kirsten Zeitler, September 27, 2016

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Key Words

deoxygenations, Hantzsch ester

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ID: J54-Y2015