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Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis

Javad Amani and Gary A. Molander*

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

J. Amani, G. A. Molander, J. Org. Chem., 2017, 82, 1856-1863.

DOI: 10.1021/acs.joc.6b02897 (free Supporting Information)



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Abstract

Visible light photoredox/nickel dual catalysis enables a cross-coupling of acyl chlorides with potassium alkyltrifluoroborates via a single-electron-mediated alkyl transfer. This protocol circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient synthesis of unsymmetrical alkyl ketones.

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Visible Light Photoredox Cross-Coupling of Acyl Chlorides with Potassium Alkoxymethyltrifluoroborates: Synthesis of α-Alkoxyketones

J. Amani, E. Sodagar, G. A. Molander, Org. Lett., 2016, 18, 732-735.


Key Words

acylations


ID: J42-Y2017