Biaryl Diketone Synthesis via Palladium‐catalyzed Carbonylative Coupling with Carbon Monoxide or Various Metal Carbonyls

Abstract

Biaryl diketones were synthesized via palladium-catalyzed carbonylative coupling in the presence of a palladium N-heterocyclic carbene complex and CO or metal carbonyls. Different arylboronic acids along with various CO-releasing molecules were tested to study the influence of structure. Generally, steric hindrance of arylboronic acids and CO-releasing ability of various metal carbonyls played significant roles. In most cases, single ketone products were found as the side products rather than direct coupling products.

Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones

“…Purification was carried out by silica gel chromatographic column (eluant: neat cyclohexane) to afford 75.2 mg of 15 (83% yield, slightly yellow solid, mp 215–216 °C). Spectroscopic data were in accordance with the literature data …”

“…Spectroscopic data were in accordance with the literature data. 46 1 H NMR (300 MHz, CDCl 3 ) δ 7.93 (d, J = 8.3 Hz, 4H), 7.87–7.82 (m, 4H), 7.77 (d, J = 8.3 Hz, 4H), 7.65–7.59 (m, 2H), 7.52 (dd, J = 8.2, 6.8 Hz, 4H). 13 C{ 1 H} NMR (75 MHz, CDCl 3 ) δ 196.3, 144.0, 137.7, 137.2, 132.7, 130.9, 130.2, 128.5, 127.3.…”

“…Spectroscopic data were in accordance with the literature data. 46 [1,1′-Biphenyl]-3,3′-dicarbonitrile (16). From 104.5 mg (0.500 mmol) of 1o, 25.0 mg (0.05 mmol, 10 mol %) of (PPh 3 )AuCl, 40.0 mg of NaHCO 3 (1.0 mmol), and 40.0 mg of 1,10-phenanthroline (0.2 mmol, 40 mol %) in 5 mL of degassed acetonitrile/water (9:1).…”

Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions

“…The methodology represents a very convenient and accessible reaction procedure, which allowed the preparation of a range of functionalized aryl alkyl ketones including the antipsychotic drug, melperone. For a recent example of biaryl ketone synthesis by metal-carbonyl-mediated Suzuki cross-coupling methodology, see also the published work by Jung et al 114…”