Pd-catalyzed ortho-arylation of 3,4-dihydroisoquinolones via C–H bond activation: synthesis of 8-aryl-1,2,3,4-tetrahydroisoquinolines

A novel counter‐selection method for markerless genetic modification in Synechocystis sp. PCC 6803

“…Direct arylation is still in its early stages of development, but some of the methodologies, reported in this review, have been used in the syntheses of natural products, their intermediates and complex ligands as well. CH bond activation has shown its remarkable applications in the synthesis of some natural products and other key intermediates, including a polydentate ligand trisbenzoquinoline in water using a ruthenium catalyst, (+)‐preclamol, hydroxytetraphenylenes, 8‐aryl‐1,2,3,4‐tetrahydroisoquinolines, derivatives of bixafen, estrones, benzochromenones, fluorenones, and phenanthridines by inter‐ and intramolecular CH bond activations leading to CC bond formation (Scheme ) 19,22,41c,105,107,111…”

“…Kim and co‐workers reported an efficient route to synthesise biologically interesting cross‐coupling products through palladium‐catalysed ortho ‐arylation of dihydroisoquinolones with aryl iodides to afford a variety of 8‐aryl‐1,2,3,4‐tetrahydroisoquinolones in moderate to high yields (50–86%) and high regioselectivities (Scheme ) 19. In this case, the introduction of the aryl group at C‐8 position was regioselectively directed by the carbonyl group present on quinolone in the presence of Pd(OAc) 2 as a catalyst, AgOAc as an additive and trifluoracetic acid as a solvent at 110 °C.…”

Palladium Catalysis: Dependence of the Efficiency of C−C Bond Formation on Carboxylate Ligand and Alkali Metal Carboxylate or Carboxylic Acid Additive. Part A: the C(sp2)−C(sp2), C(sp2)−C(sp3) and C(sp3)−C(sp3) Bonds

“…AgOAc was also used as oxidant for the Pd‐catalyzed C8‐arylation of 2‐methyl‐3,4‐dihydroisoquinolin‐1(2 H )‐one with 1‐chloro‐4‐iodobenzene, which occurred in fair yield in CF 3 CO 2 H (Scheme 2i) [23] . This result contrasts to those of Scheme 2e, for which CF 3 CO 2 H additive was detrimental to the process.…”

ChemInform Abstract: Designer‐Surfactant‐Enabled Cross‐Couplings in Water at Room Temperature

“…44 Alternatively, it has been shown that Fujiwara–Moritani coupling reactions with acrylates can be carried out in PTS–water (eq 12) 45 by using a cationic source of palladium, as in commercially available [Pd(MeCN) 4 ](BF 4 ) 2 , 46 Both benzoquinone (1 equiv) and AgNO 3 (2 equiv) are required. Double functionalization ortho to the amide directing group is not observed here as well.…”