Efficient Redox Isomerization of Allylic Alcohols under Mild Conditions Catalyzed by Arene−Ruthenium(II) Complexes
Pascale Crochet, M.A. Fernandez-Zumel, José Gimeno, Marcus Scheele
Abstract
Pascale Crochet, M.A. Fernandez-Zumel, José Gimeno, Marcus Scheele
Abstract
The catalytic activity of the arene−ruthenium(II) complexes [RuCl 2 (η 6 - p -cymene)(L)] (L = P(OPh) 3, P(OMe) 3, P(OEt) 3, PPh 3, P( p -C 6 H 4 OMe) 3, PMe 2 Ph, PMe 3, PEt 3, PCy 3 ) in the isomerization of allylic alcohols into the corresponding saturated ketones has been investigated, the best performances being obtained using [RuCl 2 (η 6 - p -cymene){P(OEt) 3 }]. This compound has proven to be able to catalyze the transformation of poorly reactive substrates of the type R 1 CH CHCH(OH)R 2 and R 1 CH C(R 2 )CH(OH)R 3 (R 1, R 2, R 3 ≠ H) under very smooth conditions.
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The catalytic activity of the arene−ruthenium(II) complexes [RuCl 2 (η 6 - p -cymene)(L)] (L = P(OPh) 3, P(OMe) 3, P(OEt) 3, PPh 3, P( p -C 6 H 4 OMe) 3, PMe 2 Ph, PMe 3, PEt 3, PCy 3 ) in the isomerization of allylic alcohols into the corresponding saturated ketones has been investigated, the best performances being obtained using [RuCl 2 (η 6 - p -cymene){P(OEt) 3 }]. This compound has proven to be able to catalyze the transformation of poorly reactive substrates of the type R 1 CH CHCH(OH)R 2 and R 1 CH C(R 2 )CH(OH)R 3 (R 1, R 2, R 3 ≠ H) under very smooth conditions.
Key concepts: Chemistry, Isomerization, Ruthenium, Allylic rearrangement, Catalysis, Medicinal chemistry, Redox, Stereochemistry