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Shibata N, Fukushi K, Furukawa T, et al. Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Org Lett. 2012;14(20):5366-9doi: 10.1021/ol302589w.
Shibata, N., Fukushi, K., Furukawa, T., Suzuki, S., Tokunaga, E., & Cahard, D. (2012). Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Organic letters, 14(20), 5366-9. https://doi.org/10.1021/ol302589w
Shibata, Norio, et al. "Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds." Organic letters vol. 14,20 (2012): 5366-9. doi: https://doi.org/10.1021/ol302589w
Shibata N, Fukushi K, Furukawa T, Suzuki S, Tokunaga E, Cahard D. Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds. Org Lett. 2012 Oct 19;14(20):5366-9. doi: 10.1021/ol302589w. Epub 2012 Oct 10. PMID: 23050610.
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Org Lett. 2012 Oct 19;14(20):5366-9. doi: 10.1021/ol302589w. Epub 2012 Oct 10.

Decarboxylative allylation of trifluoroethyl sulfones and approach to difluoromethyl compounds.

Organic letters

Norio Shibata, Kazunobu Fukushi, Tatsuya Furukawa, Satoru Suzuki, Etsuko Tokunaga, Dominique Cahard

Affiliations

  1. Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Nagoya 466-8555, Japan. [email protected]

PMID: 23050610 DOI: 10.1021/ol302589w

Abstract

Allyl carbonates undergo palladium-catalyzed decarboxylative allylation of trifluoroethyl phenyl sulfones. The success of the allylation, which is not efficient under typical strong base-mediated conditions, is the result of mild conditions thanks to a progressive delivery of ethoxide. Indeed, ethyl allyl carbonates act as a latent source of ethoxide for generation of the trifluoroethyl carbanion that reacts with the π-allylpalladium complex. The utility of the method is illustrated in a new approach to difluoromethyl compounds.

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