Rhodium(I)-Catalyzed Carboxylation of Aryl- and Alkenylboronic Esters with CO2
Top Cited Papers
- 15 June 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (27) , 8706-8707
- https://doi.org/10.1021/ja061232m
Abstract
When the esters of arylboronic acids with 2,2-dimethylpropan-1,3-diol were treated with a catalytic amount of [Rh(OH)(cod)]2 in the presence of 1,3-bis(diphenylphosphino)propane and CsF in dioxane at 60 °C under carbon dioxide atmosphere, the benzoic acid derivatives were obtained in good yields. Reactions of alkenylboronic esters also proceeded under similar conditions to give α,β-unsaturated carboxylic acids. As these boronic esters are now easily available through coupling or direct borylation reactions, this method would be a useful method for the preparation of various functionalized aryl- and alkenyl-carboxylic acids.Keywords
This publication has 20 references indexed in Scilit:
- Mechanism of the Mild Functionalization of Arenes by Diboron Reagents Catalyzed by Iridium Complexes. Intermediacy and Chemistry of Bipyridine-Ligated Iridium Trisboryl ComplexesJournal of the American Chemical Society, 2005
- Sterically Directed Functionalization of Aromatic C−H Bonds: Selective Borylation Ortho to Cyano Groups in Arenes and HeterocyclesJournal of the American Chemical Society, 2005
- Rhodium-Catalyzed 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds: Large Accelerating Effects of Bases and LigandsThe Journal of Organic Chemistry, 2003
- Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium IntermediatesJournal of the American Chemical Society, 2002
- Rhodium(I)-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated AmidesThe Journal of Organic Chemistry, 2001
- A Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds Catalyzed by 2β-CD-[Rh(OH)(cod)]2 or [RhCl(cod)]2 in a Single Aqueous MediumChemistry Letters, 2001
- Steric and Chelate Directing Effects in Aromatic BorylationJournal of the American Chemical Society, 2000
- Thermal, Catalytic, Regiospecific Functionalization of AlkanesScience, 2000
- Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic EstersThe Journal of Organic Chemistry, 1995
- Interaction of carbon dioxide with coordinatively unsaturated rhodium(I) complexes with the ligand 1,2-bis(diphenylphosphino)ethaneInorganic Chemistry, 1980