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Chiral N-heterocyclic carbene iridium catalyst for the enantioselective hydrosilane reduction of ketones
- Source :
- Journal of Molecular Catalysis A: Chemical. 421:138-145
- Publication Year :
- 2016
- Publisher :
- Elsevier BV, 2016.
-
Abstract
- Enantioselective reduction of ketones with (EtO) 2 MeSiH catalyzed by an in-situ generated N -heterocyclic carbene (NHC) Ir complex at room temperature has been developed. A series of benzimidazolium salts were synthesized and screened in the asymmetric hydrosilylation reaction. As a result, propiophenone was efficiently reduced by the combined catalytic system of [IrCl(cod)] 2 and NHC–Ag complex derived from N -(1-naphthalenylmethyl)-substituted benzimidazolium salt L12 , affording the corresponding alcohol in 92% yield and with 92% ee. Moreover, the evaluation of an Ir catalyst precursor showed that cationic [Ir(cod) 2 ]BF 4 complex could be used. Furthermore, the introduction of a chiral hydroxyamide side arm into the benzimidazolium salt was critical for the successful design of the NHC ligand.
- Subjects :
- 010405 organic chemistry
Chemistry
Hydrosilylation
Ligand
Process Chemistry and Technology
Cationic polymerization
Enantioselective synthesis
chemistry.chemical_element
010402 general chemistry
01 natural sciences
Medicinal chemistry
Catalysis
0104 chemical sciences
chemistry.chemical_compound
Propiophenone
Organic chemistry
Iridium
Physical and Theoretical Chemistry
Carbene
Subjects
Details
- ISSN :
- 13811169
- Volume :
- 421
- Database :
- OpenAIRE
- Journal :
- Journal of Molecular Catalysis A: Chemical
- Accession number :
- edsair.doi...........82e02ad70e1ddeb62d0a1e71f83e64a6