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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 10, Number 3
BKCSDE 10(3)
March 20, 1989 

Rhodium(Ⅰ) Complexes of 1,1'-Bis(diphenylphosphino)-ferrocene as Efficient Catalysts in Regioselective Hydrogenation of Polynuclear Heteroaromatic Compounds
Tae-Jeong Kim*, Kyu-Chul Lee
Two rhodium(Ⅰ) complexes of the types [Rh(BPPF)(NBD)]ClO4 (10) and [Rh(BPPF)Cl]2 (11) (BPPF = 1,1'-bis(diphenylphosphino)-ferrocene) have been prepared and investigated as catalysts for the regioselective hydrogenation of polynuclear heteroaromatic nitrogen and sulfur compounds such as quinoline (1), acridine (2), phenanthridine (3), 7,8-benzoquinoline (4), benzothiophene (5), isoquinoline (6), indole (7), pyridine (8), and thiophene (9). Both complexes 10 and 11, except for the cases of indole (7) and mononuclear heteroaromatics 8-9, are very efficient in the selective reduction under quite mild hydrogenation conditions to give the corresponding saturated nitrogen and sulfur heterocyclic analogues of 1-6 in fast conversion rates and in excellent yields. Relative rate studies revealed that the reduction depends significantly on the steric and electronic effects of the substrates. Of the two complexes 10-11, the dimeric species 11 gives faster reaction rates in all cases studied.
279 - 282
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