Ru-Catalyzed C-H Arylation of Acrylic Acids with Aryl Bromides.

Florian Belitz, Ann-Katrin Seitz, Jonas F Goebel, Zhiyong Hu, Lukas J Gooßen

Organic letters 2022 May 20

filter terms:

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.

Citation

Florian Belitz, Ann-Katrin Seitz, Jonas F Goebel, Zhiyong Hu, Lukas J Gooßen. Ru-Catalyzed C-H Arylation of Acrylic Acids with Aryl Bromides. Organic letters. 2022 May 20;24(19):3466-3470