Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol

Bi, Lei; Georg, Gunda I.

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Issue Date

2011-10-21

Author

Bi, Lei

Georg, Gunda I.

Publisher

American Chemical Society

Type

Article

Article Version

Scholarly/refereed, author accepted manuscript

Rights

This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol202202a.

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Abstract

2,3-Dihydropyridin-4(1H)-ones undergo direct C–H functionalization at C5 in the palladium(II)-catalyzed Hiyama reaction, using triethoxy(aryl)silanes and dimethylphenylsilanol. The reagent CuF2 has a dual role in the reactions with triethoxy(aryl)silanes. It is a source of fluoride to activate the silane in the Hiyama reaction and also serves as the reoxidant to convert Pd(0) to Pd(II) in the catalytic cycle.

Citation

Bi, L., & Georg, G. I. (2011). Direct Hiyama Cross-Coupling of Enaminones With Triethoxy(aryl)silanes and Dimethylphenylsilanol. Organic Letters, 13(20), 5413–5415. http://doi.org/10.1021/ol202202a

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