Improving the sustainability of the ruthenium-catalysed N-directed C–H arylation of arenes with aryl halides

Abstract

A ruthenium-catalysed C–H arylation procedure that utilises a range of green solvents in place of the undesirable solvent NMP is presented. Examples of fast reaction time, low catalyst loading and large-scale reactivity are also shown.

Benzoxazole or Benzothiazole as an Innate Directing Group for Palladium- and Ruthenium-Catalyzed Complementary C–H Arylation: Functionalization of Biorelevant Heterocyclic Scaffolds

“…36 Therefore, it was planned to test the influence of σ-donor/π-acceptor ligands to alter the electron density around the Ru(II) center. In view of the success of P-based ligands in Ru(II)-catalyzed ortho C–H arylation of heteroarenes, 12c 40a b , 40` e f probably favoring the oxidative addition of Ru(II) center to haloarenes, first we screened P-based ligands (30 mol%), such as PMe 3 and PPh 3 in the presence of [RuCl 2 ( p -cym)] 2 (5 mol%), AgBF 4 (10 mol%) as co-catalyst, and Ag 2 CO 3 (1 equiv) as an additive at 120 °C for 12 h (entries 1 and 2). The better σ-donor/π-acceptor ligand PPh 3 provided a higher conversion of 3a than PMe 3 .…”

Discovery of Dehydroabietylamine Derivatives as Antibacterial and Antifungal Agents

“…This approach enables the functionalization of both sp 2 and sp 3 carbon–hydrogen bonds, leading to the formation of a range of carbon–carbon and carbon–heteroatom bonds. This significant advancement has garnered widespread attention in the realm of organic synthesis. − Dehydroabietic acid (DHAA) derivatives, with various amide directing groups, have been employed as substrates for C–H activation, undergoing reactions such as alkylation, amination, and borylation, delivering alcohol and chlorination at the C-19 position. − Maulide explored a functionally straightforward C­(sp 3 )–H arylation procedure for the direct, late-stage alteration of dehydroabietic acid. Preliminary screening indicated the antimicrobial efficacy of the target compounds against methicillin-resistant Staphylococcus aureus (MRSA) .…”