Palladium-catalyzed oxidative coupling of aromatic compounds with olefins using t-butyl perbenzoate as a hydrogen accepter

Reactions of TpRu(CO)(NCMe)(Me) (Tp = Hydridotris(pyrazolyl)borate) with Heteroaromatic Substrates: Stoichiometric and Catalytic C−H Activation

“…22 serves as a catalyst for arylation at all three positions of pyrrole substrates as well as a catalyst for the oxidative coupling of 2-methylfuran and acrylates. 28,29 Our group has recently reported that TpRu(CO)-(NCMe)(R) (Tp ) hydridotris(pyrazolyl)borate; R ) Me or Ph) catalyzes the addition of arene C-H bonds across CdC bonds of olefins, 30 and the closely related complex TpRu(PPh 3 )(NCMe)H has been reported to activate C-H bonds. 31 We have extended studies to reactions of TpRu(CO)(NCMe)(Me) with heteroaromatic substrates and report herein the initial details of these transformations.…”

Active Pd(II) Complexes as Either Lewis Acid Catalysts or Transition Metal Catalysts

“…A benzene solution of cyclohexenecarbonitrile (45) and 10 mol% of Pd(OAc) 2 with chiral sulfonylamino-oxazoline ligand 47 in the presence of one equivalent of tert-butyl perbenzoate as a reoxidant was heated at 100°C to afford the coupling product 46 [161] (Scheme 33). Modification of the chiral ligand 47 with an electron-withdrawing and sterically demanding highly fluorinated sulfonyl group was found to lead to an increased chemical yield and enantioselectivity (up to 49% ee by 47e).…”

Transition Metal Catalyzed Coupling Reactions under C−H Activation

“…[47] A peracid is used as the oxidant in the related arylation of the acrylate 128 with the furan 127 (Scheme 28). [48] The key step in this reaction is the metalation of 127 at the electron-rich 5-position by the electrophilic palladium benzoate, which finally leads to the Heck-like product 129.…”