doi: 10.1021/ja900984x.
Synthesis of aromatic esters via Pd-catalyzed decarboxylative coupling of potassium oxalate monoesters with aryl bromides and chlorides
Affiliations
- PMID: 19338301
- DOI: 10.1021/ja900984x
Item in Clipboard
Synthesis of aromatic esters via Pd-catalyzed decarboxylative coupling of potassium oxalate monoesters with aryl bromides and chlorides
J Am Chem Soc.
.
Abstract
Pd-catalyzed decarboxylative cross-coupling of aryl iodides, bromides, and chlorides with potassium oxalate monoesters has been discovered. This reaction is potentially useful for laboratory-scale synthesis of aryl and alkenyl esters. Bulky, electron-rich bidentate phosphine ligands are preferred in the reaction, whereas Cu is not needed for decarboxylation. Theoretical calculations suggest a five-coordinate Pd(II) transition state for decarboxylation with an energy barrier of approximately 30 kcal/mol.
Similar articles
-
Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates.Org Lett. 2010 Mar 5;12(5):1000-3. doi: 10.1021/ol100008q. Org Lett. 2010. PMID: 20187653
-
Theoretical analysis of factors controlling Pd-catalyzed decarboxylative coupling of carboxylic acids with olefins.J Am Chem Soc. 2010 Jan 20;132(2):638-46. doi: 10.1021/ja907448t. J Am Chem Soc. 2010. PMID: 20038103
-
Biaryl and aryl ketone synthesis via Pd-catalyzed decarboxylative coupling of carboxylate salts with aryl triflates.Chemistry. 2009 Sep 21;15(37):9336-49. doi: 10.1002/chem.200900892. Chemistry. 2009. PMID: 19718720
-
Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides.J Am Chem Soc. 2007 Apr 18;129(15):4824-33. doi: 10.1021/ja068993+. Epub 2007 Mar 22. J Am Chem Soc. 2007. PMID: 17375927
-
9-fluorenylphosphines for the Pd-catalyzed sonogashira, suzuki, and Buchwald-Hartwig coupling reactions in organic solvents and water.Chemistry. 2007;13(9):2701-16. doi: 10.1002/chem.200601142. Chemistry. 2007. PMID: 17200923
Cited by
-
Direct Minisci-Type C-H Amidation of Purine Bases.Org Lett. 2022 Nov 4;24(43):8008-8013. doi: 10.1021/acs.orglett.2c03206. Epub 2022 Oct 26. Org Lett. 2022. PMID: 36285836 Free PMC article.
-
Recent Advances in Visible-Light-Mediated Amide Synthesis.Molecules. 2022 Jan 14;27(2):517. doi: 10.3390/molecules27020517. Molecules. 2022. PMID: 35056829 Free PMC article. Review.
-
Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes.Chemistry. 2021 Feb 19;27(11):3682-3687. doi: 10.1002/chem.202005158. Epub 2021 Jan 25. Chemistry. 2021. PMID: 33283370 Free PMC article.
-
Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity.J Enzyme Inhib Med Chem. 2020 Dec;35(1):935-949. doi: 10.1080/14756366.2020.1748024. J Enzyme Inhib Med Chem. 2020. PMID: 32249633 Free PMC article.
-
Electronic Effect-Guided, Palladium-Catalyzed Regioselective B-H Activation and Multistep Diarylation of o-Carboranes with Aryl Iodides.ACS Omega. 2019 Jan 8;4(1):465-474. doi: 10.1021/acsomega.8b02654. eCollection 2019 Jan 31. ACS Omega. 2019. PMID: 31459344 Free PMC article.
LinkOut - more resources
Full Text Sources
Other Literature Sources
