By Prof. L. Brandsma, Prof. H. D. Verkruijsse, Prof. S. F. Vasilevsky (auth.)
Homogeneous catalysis is a vital procedure for the synthesis of high-valued chemical substances. L. Brandsma has conscientiously chosen and checked the experimental strategies illustrating the catalytic use of copper, nickel, and palladium compounds in natural synthesis. All methods are on a preparative scale, make monetary use of solvents and catalysts, stay away from poisonous components and feature excessive yields.
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Extra resources for Application of Transition Metal Catalysts in Organic Synthesis
P. 6505, in -80% yield. The compound should be stored at a dark place, preferably in the refrigerator. 7 (1H) ppm. When THF-hexane was used instead of Et20-hexane, appreciable amounts of 2,3and 2,5-diodothiophene were formed as a result of metallation of 2-iodothiophene by 2-lithiothiophene and subsequent iodination. 13 3-lodothiophene n-BuLi THF - - oMgB_r_I_2__ o 1 s S The procedure is described in L. D. Verkruijsse, Preparative Polar Organometallic Chemistry, Vol. I, p. 157, Springer-Verlag, Heidelberg (1987).
6 g) was added in one portion, after which the temperature was allowed to rise to 0 0C. After hydrolysis and drying the organic layer over anhydrous MgS04' the solvent was removed in vacuo. 5 mmHg. The product was obtained in almost quantitative yield. If desired, the product can be distilled at <2 mm pressure. 54 (s, 3H) ppm. 7 4-Methyl-2-tributylstannylthiazole Scale and equipment: same as in preceding experiments. 11 mol of n-BuLi in -70 ml of hexane and 70 ml of THF, while keeping the temperature between -65 and -SO 0C.
P. 6288, in an excellent (~90%) yield. The product is rather stable at room temperature. 75 ppm. Note: After dilution with a small amount of water, the upper layer can be used for repetition of the experiment. 2,5-Dibromothiophene can also prepared by the hydrogen peroxide method (see expo in Sect. 1). In this case the double molar amounts ofH 2 0 2 and HBr are used. The last portions of peroxide react at temperatures above 30°C. 3 2,3,5-Tribromothiophene o 48 % aq. HBr + 3Br2 S 20 --7 80°C .. 50 molar (thiophene).