By L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse
Homogeneous catalysis is a crucial process for the synthesis of high-valued chemical compounds. L. Brandsma has rigorously chosen and checked the experimental approaches illustrating the catalytic use of copper, nickel, and palladium compounds in natural synthesis. All strategies are on a preparative scale, make monetary use of solvents and catalysts, stay away from poisonous ingredients and feature excessive yields.
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Additional info for Application of Transition Metal Catalysts in Organic Synthesis (Springer Laboratory)
The distillate, collected in a strongly cooled, single receiver, was redistilled through a 20-cm Vigreux column. p. 599, was obtained in yields of up to -91 %. In general it is advisable to distill smaller portions at water-aspirator pressure, as 2halopyrroles are unstable. The product should be stored at -20 0c. 17 1-Bromo-4-iodobenzene Br ¢ Et,O + n-RuLi Br -80 ~ 0 °C .. ¢ 0Y Br Br __ 12 _ (+ BuBr) <-40°C .. 10 molar. Apparatus: 1-1 round-bottomed, three-necked flask, equipped with a nitrogen inletthermometer combination, a mechanical stirrer and an outlet; for the iodination the outlet was replaced by a powder funnel.
The yield of the crude, dry product was 62% (calculated on methyI2-furancarboxylate). The product was mixed with 40 g of copper powder and 350 ml of quinoline and the mixture was heated in an oil bath at 180°C until the evolution of carbon dioxide had ceased. p. 2 Aryl and Hetaryl Halides was obtained in 65% yield by careful fractional distillation through a 30-cm Widmercolumn. The compound is stable at room temperature. 35 ppm (2H). 50 molar. Apparatus: I-I round-bottomed, three-necked flask, equipped with a dropping funnel-nitrogen inlet combination, a mechanical stirrer and a thermometer-outlet combination.
RC"'CLi + 12 THF or Eto O-hexane " ... 20 molar. Apparatus: 1-1 round-bottomed, three-necked flask, equipped with a dropping (or powder) funnel-nitrogen inlet combination, a mechanical stirrer and a thermometeroutlet combination. 20 mol of the lithiated acetylene (see literature mentioned above) in a mixture of Et20 and hexane or THF and hexane with cooling between -15 and -30°C. After this addition, the cooling bath was removed and the temperature was allowed to rise to about 0 °C (suspensions of RC==CLi may react more slowly).
Application of Transition Metal Catalysts in Organic Synthesis (Springer Laboratory) by L. Brandsma, S.F. Vasilevsky, H.D. Verkruijsse