The First Suzuki Cross-Coupling of Aryltrimethylammonium Salts

General Information. Commercial reagents were purchased from Aldrich or Strem and used as suppplied. Reactions were conducted using standard drybox techniques. Non-aqueous reagents were transferred under argon via syringe. Organic solutions were concentrated under reduced pressure on a Büchi rotary evaporator. Dioxane was distilled from sodium benzophenone ketyl and then degassed using the freeze-pump-thaw method (4 cycles) prior to use. Chromatographic purification of products was accomplished using forced-flow chromatography on ICN 60 32-64 mesh silica gel 63 according to the method of Still. Thinlayer chromatography (TLC) was performed on EM Reagents 0.25 mm silica gel 60-F plates. Visualization of the developed chromatogram was performed by fluorescence quenching or iodine stain. H and C NMR spectra were recorded on a Varian Mercury 300 spectrometer (300 MHz and 75 MHz) as noted, and are internally referenced to residual protio solvent signals. Data for H NMR are reported as follows: chemical shift (δ ppm), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad), integration and coupling constant (Hz). Data for C NMR are reported in terms of chemical shift. IR spectra were recorded on a Perkin Elmer Paragon 1000 spectrometer and are reported in terms of frequency of absorption (cm). Mass spectra were obtained on a JEOL JMS-600H spectrometer. Melting points were recorded on a Thomas Hoover capillary melting point apparatus, and are uncorrected. General Procedure: A N,N,N-trimethylanilinium trifluoromethanesulfonate (0.157 mmol), Ni(COD)2 (4.3 mg, 0.0157 mmol), IMes⋅HCl (5.4 mg, 0.0157 mmmol), a boronic acid (1.1 or 2 equivalents) and CsF (73 mg, 0.471 mmol) were combined in a 2 dram screw-capped vial containing a magnetic stirrer bar under a nitrogen atmosphere. The vial was sealed with a cap containing a teflon coated septum, removed from the drybox and charged with dioxane (1.0