Preparation of Alkenes by C-Vinylation

I penmenial Procedure 5.1 Meek reaction with a polvsiv rcnc-bound aryl iodide 

To Rink amide resin iieylated with. 1-iodobenzyloxy acetic acid (0.2 g, 0.094 mmol) were added DMA (4.7 mL), sodium acetate (23 mg, 0.28 mmol, 3 equiv.), B114NCI (56 mg, 0.20 mmol, 2 equiv.), and dimethyl itaconate (119 mg, 0.75 mmol, 

8 equiv.), and the mixture was degassed for 20 min. Palladium(U) acetate (5 mg, 0.022 mmol, 0.2 equiv.) was then added and the mixture was shaken at 100 °C for 24 h. The support was subsequently washed with dioxane, water, ethanol, and further dioxane, and the coupling reaction was repeated once more. After extensive washing, the support was dried under reduced pressure and treated with TFA/ DCM (2 8 5 mL, 4x1 min). The combined filtrates were concentrated. The residue was dried by coevaporation of the solvents with toluene (4 x) and dried under reduced pressure to yield 33 mg of the coupling product, which was slightly contaminated with tetrabutylammonium salts. The yield after purification was 67%. 

In the Suzuki reaction, an aryl iodide or synthetic equivalent thereof is coupled with an arylboronic acid or a borane, again using palladium(O) as the catalyst. This reaction is usually used to prepare biaryls, and few examples have been reported of the solid-phase synthesis of alkenes by means of a Suzuki coupling (Table 5.8). 

---