Morpholine (Aldrich),
4-Chlorotoluene (Aldrich),
bis(1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene)palladium(0) (see Page 90),
KO^tBu (Aldrich, sublimed twice at 157 ^oC, 1x10^-5 mbar).

Bis(1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene)palladium(0) (14 mg, 0.016 mmol) and KOtBu (133 mg, 1.19 mmol) were placed in an ampoule fitted with a teflon stopcock in a glovebox and the ampoule sealed. The ampoule was removed from the glovebox and a septum fitted under a flow of argon. Dioxane (10 mL) was added. 4-Chlorotoluene (93 microL, 0.79 mmol) followed by morpholine (83 microL, 0.95 mmol) were injected through the septum into the ampoule. The ampoule was resealed and the mixture heated at 100 ^oC for 30 mins. The reaction was judged to be complete by HPLC analysis and the mixture was then cooled to ambient temperature. The solvent was removed in vacuo and the mixture filtered through a silica plug with 20 % EtOAc/hexane. After removal of the solvent a white solid was obtained. The solid was dried under vacuum to yield the product (137 mg, 98% yield).

This reaction has been performed 3 times on the same scale and works well. The catalyst loading can be reduced to 0.02 mol% and the reaction still goes to 100% conversion by HPLC analysis after heating at 100 ^oC for 16 h. Non sublimed KO^tBu has been used in the reaction with no loss of yield. The solid reactants can be weighed in the air provided that the storage and reaction vessels are air tight and are placed under an inert atmosphere after exposure to air. This is easily achieved by attaching the vessels to a double manifold and cycling the vessels vacuum/argon three times. Other amines used in this reaction (all at 100 ^oC) are as follows: dibutylamine (5 h, 97%), hexylamine (4eq. of amine, 5 h, 81%), aniline (1 h, 99%), N-methylaniline (1 h, 99%), benzophenoneimine (1 h, 98%) (percentages represent isolated yields).

¹H nmr (CDCl₃): 2.30 (s, 3H, Ar-CH₃), 3.12 (t, 4H, CH₂, ³J(HH) = 4.8 Hz), 3.88 (t, 4H, CH₂, ³J(HH) = 4.8 Hz), 6.86 (d, 2H, Ar-CH, ³J(HH) = 8.4 Hz), 7.11 (d, 2H, Ar-CH, ³J(HH) = 8.4 Hz).

See supplementary information for: Titcomb, L. R.; Caddick, S.; Cloke, F. G. N.; Wilson, D. J. W.; McKerrecher, D. Chem. Commun., 2001, 1388.

1. Shriver, D. F.; The Manipulation of Air Sensitive Compounds, McGraw-Hill, New York, 1989. 2. Caddick, S.; Cloke, F. G. N.; Clentsmith, G. K. B.; Hitchcock, P. B.; McKerrecher, D.; Titcomb, L. R.; Williams, M. R. V. J. Organomet. Chem., 2001, 617, 635.