Transition metal catalysis in fluorous media: application of a new immobilization principle to rhodium-catalyzed hydrogenation of alkenes Academic Article uri icon

abstract

  • Biphase systems were generated by combining toluene solutions of alkenes (2-cyclohexen-1-one, 1-dodecene, cyclododecene, 4-bromostyrene) and CF3C6F11 solutions of the pre-catalyst C1Rh[P(CH2CH2(CF2)5CF 3)3]3 ((1); 1.1-0.8 mol%) and placed under 1 atm of H2. The perfluoroalkyl segments in (1) confer high affinities for fluorocarbons. After 8-26 h at 45°C, the CF3C6F11 phases were separated, and extracted with an equal volume of toluene. GLC analyses of the toluene solutions showed 98-87% yields of the hydrogenation products cyclohexanone, dodecane, cyclododecane, and 4-bromoethylbenzene (turnover numbers 120-87). The CF3C6F11 phases were charged with new toluene solutions of 2-cyclohexen-1-one or 1-dodecene, and similarly treated with H2. There was no significant loss of catalyst activity over three cycles. A preparative reaction gave cyclohexanone in 89% yield. Some C=C isomerization could be detected during the course of 1-dodecene hydrogenation, and (1) gave a dihydride complex in the absence of alkene. © 1998 Elsevier Science B.V. All rights reserved.

altmetric score

  • 3

author list (cited authors)

  • Rutherford, D., Juliette, J., Rocaboy, C., Horváth, I. T., & Gladysz, J. A.

citation count

  • 63

publication date

  • July 1998