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

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

DOI: 10.1021/acs.orglett.5b03705 (free Supporting Information)


Abstract

An operationally simple and mild visible-light, single-electron-transfer (SET), photoredox cross-coupling enables the synthesis of α-alkoxyketones in high yields from various aliphatic and aromatic acyl chlorides and structurally diverse potassium alkoxymethyltrifluoroborates. The bond connection is unique to both alkylboron chemistry and photoredox/Ni catalysis.


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

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


Key Words

α-hydroxy carbonyl compounds, acylation


ID: J54-Y2016