Highly Efficient Alkylation to Ketones and Aldimines with Grignard Reagents Catalyzed by Zinc(II) Chloride
Authors:
- 14 July 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (31) , 9998-9999
Abstract
A highly efficient alkylation to ketones and aldimines with Grignard reagents in the presence of catalytic trialkylzinc(II) ate complexes derived from ZnCl2 (10 mol %) in situ was developed. This simple Zn(II)-catalyzed alkylation could minimize the well-known but serious problems with the use of only Grignard reagents, which leads to reduction and aldol side products, and the yield of desired alkylation products could be improved.Keywords
This publication has 19 references indexed in Scilit:
- Unusual Structure and Reactivity of a Homoleptic “Super‐Ate” Complex of Iron: Implications for Grignard Additions, Cross‐Coupling Reactions, and the Kharasch DeconjugationAngewandte Chemie International Edition, 2006
- Soluble Lanthanide Salts (LnCl3⋅2 LiCl) for the Improved Addition of Organomagnesium Reagents to Carbonyl CompoundsAngewandte Chemie International Edition, 2006
- Selective Iron-Catalyzed Cross-Coupling Reactions of Grignard Reagents with Enol Triflates, Acid Chlorides, and DichloroarenesThe Journal of Organic Chemistry, 2004
- Grignard reagent mediated reaction of Cp2Zr(ii)–ethylene complex with iminesChemical Communications, 2000
- Design, Reactivities, and Practical Application of Dialkylzinc Hydride Ate Complexes Generated in Situ from Dialkylzinc and Metal Hydride. A New Methodology for Activation of NaH and LiH under Mild ConditionsJournal of the American Chemical Society, 1997
- A Novel Polymer for a 193-nm Resist.Journal of Photopolymer Science and Technology, 1996
- LiClO4‐Promoted Addition of Alkyl Grignard and Alkynyllithium Reagents to Ketones. Comparison of a 5 M LiClO4/Diethyl Ether Solution with CeCl3European Journal of Inorganic Chemistry, 1995
- Reactions of dialkylmagnesium-salt mixtures with ketones: increasing the ratio of addition to reductionThe Journal of Organic Chemistry, 1990
- Reactions of carbonyl compounds with Grignard reagents in the presence of cerium chlorideJournal of the American Chemical Society, 1989
- Steric assistance in the solvolysis of 2-alkyl-2-adamantyl p-nitrobenzoatesJournal of the American Chemical Society, 1972