The Barbier−Grignard-Type Carbonyl Alkylation Using Unactivated Alkyl Halides in Water
- 14 March 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (14) , 4062-4063
- https://doi.org/10.1021/ja029649p
Abstract
The aqueous Barbier−Grignard-type alkylation of aldehydes with unactivated alkyl iodides and bromides was developed. By using a combination of zinc and cuprous iodide, catalyzed by indium(I) chloride, we successfully added tertiary, secondary, and primary alkyl halides to various aromatic aldehydes in 0.07 M aqueous Na2C2O4. A mechanistic rationale for the success of the reaction has been proposed.Keywords
This publication has 11 references indexed in Scilit:
- Quasi-Nature Catalysis: Developing C−C Bond Formations Catalyzed by Late Transition Metals in Air and WaterAccounts of Chemical Research, 2002
- Grignard type reaction via C–H bond activation in waterGreen Chemistry, 2002
- Silver catalyzed zinc Barbier reaction of benzylic halides in waterTetrahedron Letters, 1998
- A New and Practical Synthesis of α-Amino Acids from Alkenyl Boronic AcidsJournal of the American Chemical Society, 1997
- Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applicationsTetrahedron, 1996
- Indium-mediated coupling of aldehydes with prop-2-ynyl bromides in aqueous mediaJournal of the Chemical Society, Chemical Communications, 1995
- Carbon-carbon bond formation in aqueous ethanol: diastereoselective transformation of unprotected carbohydrates to higher carbon sugars using allyl bromide and tin metalJournal of the American Chemical Society, 1991
- Hydrophobic effects on simple organic reactions in waterAccounts of Chemical Research, 1991
- Crossed aldol type condensation reactions in aqueous mediaJournal of the Chemical Society, Chemical Communications, 1990
- Allylation of aldehydes and ketones in the presence of water by allylic bromides, metallic tin, and aluminumOrganometallics, 1983