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Asymmetric 1,4-Addition of Organoboronic Acids to α,β-Unsaturated Ketones and 1,2-Addition to Aldehydes Catalyzed by a Palladium Complex with a Ferrocene-based Phosphine Ligand by Yoshinori Suzuma; Shoko Hayashi; Tetsuya Yamamoto; Yohei Oe; Tetsuo Ohta; Yoshihiko Ito is a Chemistry article available to read on EtoBox.
What is Asymmetric 1,4-Addition of Organoboronic Acids to α,β-Unsaturated Ketones and 1,2-Addition to Aldehydes Catalyzed by a Palladium Complex with a Ferrocene-based Phosphine Ligand about?
A combination of palladium with ferrocene-based phosphine ligand with a carbon-bromine bond was found to be a good catalyst for the 1,4-addition of arylboronic acids to a,b-unsaturated ketones and the 1,2-addition to aldehydes. Using Pd(dba) 2 and (S,R p )-[1-(2-bromoferrocenyl)ethyl]diphenylphosphine (S,R p )-1, 3-phenylcyclohexanone was obtained from the reaction of 2-cyclohexen-1-one with phenylboronic acid in the presence of K 2 CO 3 in toluene at room temperature after 3 h in 92% yield with 76% ee. In the 1,2-addition of 4-methylphenylboronic acid to benzaldehyde, 96% of (4-methylphenyl)phenylmethanol was afforded after 24 h, while the enantiomeric excess was only 6%.
Who reads Asymmetric 1,4-Addition of Organoboronic Acids to α,β-Unsaturated Ketones and 1,2-Addition to Aldehydes Catalyzed by a Palladium Complex with a Ferrocene-based Phosphine Ligand?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Yoshinori Suzuma; Shoko Hayashi; Tetsuya Yamamoto; Yohei Oe; Tetsuo Ohta; Yoshihiko Ito
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)
- Published
- 2009
- Language
- EN
- Field
- Chemistry (Physical Sciences)