Ru-Catalyzed (E)-Specific ortho-C–H Alkenylation of Arenecarboxylic Acids by Coupling with Alkenyl Bromides

Autor:	Florian Papp, Lukas J. Gooßen, Guodong Zhang, Zhiyong Hu, Florian Belitz
Rok vydání:	2021
Předmět:	Coupling (electronics) chemistry.chemical_compound Chemistry Organic Chemistry Functional group Physical and Theoretical Chemistry Selectivity Biochemistry Medicinal chemistry Phosphine Catalysis
Zdroj:	Organic Letters. 23:3541-3545
ISSN:	1523-7052 1523-7060
Popis:	In the presence of [p-cymene)RuCl2]2, (E)-configured alkenyl bromides couple with aromatic carboxylates to form ortho-vinylbenzoic acids. This C-H vinylation proceeds in high yields without any activating phosphine ligands and has an excellent functional group tolerance. Starting from commonly available (E/Z )-mixtures of alkenyl bromides, (E)-configured vinyl arenes or dienes are formed exclusively. Mechanistic studies show that this selectivity is achieved because the (E)-configured alkenyl bromides undergo a smooth coupling, whereas the (Z)-isomers are rapidly eliminated with the formation of alkynes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::06c8a32a756e373b7c6aec4783b93fb5 https://doi.org/10.1021/acs.orglett.1c00956 Zobrazit plný text záznamu