Bulletin of the Korean Chemical Society

  • 제13권4호
  • /
  • Pages.391-395
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  • 1992
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Carbonylation of Benzyl Alcohols and Benzyl Bromide to Phenylacetic Acids with Rhodium(Ⅰ) and Iridium(Ⅰ) Complexes

  • 발행 : 1992.08.20
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초록

Rhodium(I) and iridium(II) complexes, M(Cl$O_4$)(CO)$(PPh_3)_2$ and [M(CO)$(PPh_3)_3$]Cl$O_4$ (M = Rh, Ir), and RhX(CO)$(PPh_3)_2$ (X = Cl, Br, OH) catalyze the carbonylation of benzyl alcohols to produce phenylacetic acids under 6 atm of CO at $110^{\circ}C$ in deuterated chloroform. Benzyl alcohols initially undergo dehydration to give dibenzyl ethers which are then carbonylated to benzyl phenylacetates, and the hydrolysis of benzyl phenylacetate produces phenylacetic acids and benzyl alcohols. The carbonylation is accompanied with dehydrogenation followed by hydrogenolysis of benzyl alcohols giving benzaldehydes and methylbenzenes which are also produced by CO2 elimination of phenylacetic acids. Phenylacetic acid is also produced in the reactions of benzyl bromide with CO catalytically in the presence of Rh(Cl$O_4$)(CO)$(PPh_3)_2$ and $H_2O$, and stoichiometrically with Rh(OH)(CO)$(PPh_3)_2$ in the absence of $H_2O$.

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피인용 문헌

  1. Transition metals in organic synthesis. Annual survey covering the year 1992 vol.477, pp.1, 1992, https://doi.org/10.1016/0022-328x(94)88094-8
  2. Palladium-catalyzed carbonylation of benzyl chlorides to phenylacetic acids - A new two-phase process vol.116, pp.1, 1992, https://doi.org/10.1016/s1381-1169(96)00119-7
  3. Catalytic challenges and strategies for the carbonylation of σ-bonds vol.23, pp.2, 1992, https://doi.org/10.1039/d0gc02343d