Journal
TETRAHEDRON-ASYMMETRY
Volume 16, Issue 21, Pages 3520-3526Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2005.08.059
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The [Ru-II(D-4-Por*)(CO)(McOH)] (D-4-H(2)Por*=tetrakis[(1S,4R,5R,SS)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl]porphyrin) complex 1 is an effective catalyst for asymmetric hydroxylation of aromatic hydrocarbons with 2,6-dichloropyridine N-oxide (Cl(2)pyNO) as terminal oxidant. Up to 76% ee was achieved for the catalytic hydroxylation of 4-ethyltoluene, 1,1-diethylindan and benzylcyclopropane. Both electron-donating and -withdrawing substituents were found to accelerate the catalytic oxidation reaction, and a large primary H/D kinetic isotope effect (k(H)/k(D) = 11 at 298 K) was observed for the catalytic ethylbenzene-d(10) oxidation. A mechanism involving rate-limiting hydrogen atom abstraction by reactive oxoruthenium species is postulated. (c) 2005 Elsevier Ltd. All rights reserved.
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