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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ru-Catalyzed C-H Arylation of Acrylic Acids with Aryl Bromides
Florian Belitz1, Ann-Katrin Seitz1, Jonas F Goebel1
1Department of Chemistry and Biochemistry, Ruhr-Universität Bochum, NC 2/170, Universitätsstrasse 150, 44801 Bochum, Germany.
Abstract:
In the presence of a [Ru(p-cymene)Cl2]2/triethylphosphine/lithium carbonate catalyst system, aryl bromides undergo (Z)-selective couplings with unprotected 2-arylacrylic acids to form (Z)-diarylacrylic acids. This vinylic C-H functionalization proceeds in high yields of up to 94% and (Z/E)-ratios of up to 99:1, tolerating a wide range of functional groups. Mechanistic studies indicate that the vinylic C-H activation proceeds via base-assisted cyclometalation rather than via a Heck-type mechanism, which explains its orthogonal stereoselectivity.
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