Palladium 2 acetate

Commercially available chemicals, including 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (TCI), 10,11-dihydro-5H-dibenz[b,f]azepine (TCI), 9,10-dihydro-9,9-dimethylacridine (TCI), phenoxazine (Alfa-Aesar), phenothiazine (TCI), potassium carbonate (Sigma-Aldrich), palladium(II) acetate (Sigma-Aldrich), tri-tert-butylphosphine (Sigma-Aldrich), and DMAC-Ph (TCI) were used without further purification, unless otherwise stated. All glassware, magnetic stir bars, syringes, and needles were dried in a convection oven at 120 °C. Reactions were monitored by using thin-layer chromatography (TLC). Commercial TLC plates (silica gel 254, Merck Co.) were developed, and the spots were visualized under UV irradiation at wavelengths of 254 or 365 nm. Silica gel column chromatography was performed with silica gel 60G (particle size 0.040–0.063 mm, Merck Co.). ¹H NMR (300 MHz) and ¹³C{¹H} NMR (126 MHz) spectra were collected with Bruker, AVANCE III 300 and 500 spectrometers, respectively. Chemical shifts were referenced to the peaks due to a residual solvent. Low- and high-resolution mass spectra were recorded by using an Agilent Technologies 6890 series mass spectrometer.

MAX
phase (Ti₃AlC₂) was purchased from Y-Carbon,
Ltd., Ukraine. All
of the other chemicals, hydrochloric acid, lithium fluoride, silver
nitrate, and palladium(II) acetate, were purchased from Sigma-Aldrich,
analytical grade, and were used as received. In all experiments, deionized
(DI) reagent-grade water (≥18.2 MΩ) was used. The wastewater
samples were collected from a local paper recycling factory.

Palladium(II) acetate (Pd(OAc)₂, ≥99.9%), bis[(2-diphenylphosphino)phenyl]ether (DPEphos, 98%), 2-methyl-3-buten-2-ol (98%), and 1-butyl-3-methylimidazolium chloride ([BMIM]Cl, ≥98%) were obtained from Sigma-Aldrich (Søborg, Denmark) and diethyl ether (DEE, ≥99% GPR RECTAPUR®) from VWR Chemicals (Søborg, Denmark) and all were used without further purification. Dichloromethane (DCM, 99%) was obtained from Sigma-Aldrich and dried in a solvent distributor before use. Carbon monoxide (CO, 99.97%), hydrogen (H₂, 99.999%), and nitrogen (N₂, 99.99%) were obtained from Air Liquide Denmark (Taastrup, Denmark) and used as received.

All moisture-sensitive reagents were manipulated under a nitrogen atmosphere using Schlenk and syringe techniques. Glassware was dried in an oven at 200°C and cooled under a nitrogen atmosphere. Palladium(II) acetate, triphenylphosphine, the diamines and the iodoindole substrates (7-iodoindole and 5-iodoindole) were purchased from Sigma-Aldrich and were used without further purification. Nuclear magnetic resonance (NMR) spectra were recorded on a Bruker Avance 400 spectrometer, operating at 400.13 MHz for ¹H NMR and 100.62 MHz for ¹³C NMR. Chemical shifts (δ) are reported in ppm relative to CDCl₃ (7.26 and 77.16 ppm for ¹H and ¹³C, respectively) or tetramethylsilane (TMS). High-resolution mass spectrometry (HRMS) analysis was carried out on a Bruker Microtof apparatus, equipped with a selective electrospray ionization (ESI) detector. The specific rotation [α] was measured using an electrical polarimeter (Optical Activity AA-5). Melting points, with uncorrected values, were determined with a capillary microscope electrothermal melting point apparatus. The Fourier transform infrared (FT-IR) spectra were measured in KBr pellets using a Thermo Scientific Nicolet 380 spectrometer.

Tetraethyl orthosilicate
(TEOS, 98%), 1H,1H,2H,2H-perfluorodecyltriethoxysilane (PFDTES, 97%),
(3-mercaptopropyl)triethoxysilane (MPTES, >80%), isobutyltriethoxysilane
(IBTES, ≥95%), trichloro(1H,1H,2H,2H-perfluorooctyl)silane
(97%), 3-Aminopropyltriethoxysilane (APTES, 99%), lithium hydroxide
pellets (99%), ammonium hydroxide solution (28–30%), Rhodamine
B isothiocyanate (mixed isomer), anhydrous ethanol (99.9%), acetonitrile
(99.8%), tetrahydrofuran (99.9%), palladium(II) acetate (98%), and
potassium borohydride (KBH₄, 98%), all purchased from Sigma-Aldrich,
were used to prepare the catalytic organosilica particles and isopropyl-based
POSS. Benzyl alcohol (>99%), benzaldehyde (99%), anhydrous ethanol
(99.9%), acetone (>99.5%), decane (>99%), isopropanol (≥99.5%),
dodecane (≥99%), methanol (≥99.8%), dichloromethane
(≥99.8%), octane (≥98%), 1-octene (98%), and toluene
(≥99.5%), also supplied by Sigma-Aldrich, were used for the
foaming tests and oxidation reactions.

The chemicals used were obtained from commercial suppliers of different companies and were of analytical grades. Hydroxypropyl methylcellulose (HPMC) average Mn ∼10 000, ethanol (99.9%) was obtained from Monitoring Control Laboratories Ltd, palladium(ii) acetate (98%) (C₄H₆O₄Pd), tetraethyl orthosilicate (TEOS) (99%), and acetophenone (99%) (C₈H₈O) were bought from Sigma-Aldrich. n-Decane, (CH₃(CH₂)₈CH₃) (99%) was purchased from Alfa Aesar, magnesium sulphate dried (MgSO₄) (52–70%) was obtained from Rochelle chemicals, sodium borohydride (NaBH₄) (≥98.0%) was purchased from Sisco Research Laboratories (SRL) Pvt. While ethyl acetate, sodium bicarbonate NaHCO₃ (99.50%), and NaOH (99.90%) were obtained from Promack chemicals. Milli-Q water of 18.2 MΩ cm was used to prepare all the solutions.