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Capaldo L, Buzzetti L, Merli D, et al. Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids. J Org Chem. 2016;81(16):7102-9doi: 10.1021/acs.joc.6b00984.
Capaldo, L., Buzzetti, L., Merli, D., Fagnoni, M., & Ravelli, D. (2016). Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids. The Journal of organic chemistry, 81(16), 7102-9. https://doi.org/10.1021/acs.joc.6b00984
Capaldo, Luca, et al. "Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids." The Journal of organic chemistry vol. 81,16 (2016): 7102-9. doi: https://doi.org/10.1021/acs.joc.6b00984
Capaldo L, Buzzetti L, Merli D, Fagnoni M, Ravelli D. Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids. J Org Chem. 2016 Aug 19;81(16):7102-9. doi: 10.1021/acs.joc.6b00984. Epub 2016 Jul 05. PMID: 27322957.
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J Org Chem. 2016 Aug 19;81(16):7102-9. doi: 10.1021/acs.joc.6b00984. Epub 2016 Jul 05.

Smooth Photocatalyzed Benzylation of Electrophilic Olefins via Decarboxylation of Arylacetic Acids.

The Journal of organic chemistry

Luca Capaldo, Luca Buzzetti, Daniele Merli, Maurizio Fagnoni, Davide Ravelli

Affiliations

  1. PhotoGreen Lab, Department of Chemistry, University of Pavia , Viale Taramelli 12, 27100 Pavia, Italy.

PMID: 27322957 DOI: 10.1021/acs.joc.6b00984

Abstract

Arylacetic acids were used as sources of benzyl radicals under tetrabutylammonium decatungstate photocatalyzed conditions for the benzylation of electron-poor olefins. The reaction proceeds smoothly in a mixed aqueous medium (MeCN/H2O 2/1) in the presence of NaHCO3, NaClO4, and an electron transfer agent (biphenyl). The reaction tolerates a wide variety of functional groups on the aromatic ring (whether electron donating or electron withdrawing) and can be extended to heteroaromatic analogues. The olefins have the double role of radical trap and electron acceptor. The present approach can also be extended to arylpropionic acids (including the nonsteroidal anti-inflammatory drugs ibuprofen and flurbiprofen), as well as mandelic acid derivatives.

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