The First General Palladium Catalyst for the Suzuki−Miyaura and Carbonyl Enolate Coupling of Aryl Arenesulfonates
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- 9 September 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (39) , 11818-11819
- https://doi.org/10.1021/ja036947t
Abstract
The first general method for the palladium-catalyzed Suzuki−Miyaura and carbonyl enolate coupling of unactivated aryl arenesulfonates was developed utilizing XPhos, 1, and Pd(OAc)2. This is of significant interest because aryl tosylates and aryl benzenesulfonates are more easily handled and considerably less expensive than aryl triflates. This catalyst system effects the coupling of a variety of aryl, heteroaryl, and extremely hindered arylboronic acids with different aryl tosylates, under mild conditions. The same catalyst was employed in the first carbonyl enolate coupling of aryl arensulfonates.Keywords
This publication has 11 references indexed in Scilit:
- Expanding Pd-Catalyzed C−N Bond-Forming Processes: The First Amidation of Aryl Sulfonates, Aqueous Amination, and Complementarity with Cu-Catalyzed ReactionsJournal of the American Chemical Society, 2003
- Mechanistic Insights into the Pd(BINAP)-Catalyzed Amination of Aryl Bromides: Kinetic Studies under Synthetically Relevant ConditionsJournal of the American Chemical Society, 2002
- Organoboron CompoundsPublished by Springer Nature ,2002
- Palladium-Catalyzed α-Arylation of EstersJournal of the American Chemical Society, 2001
- Catalytic Coupling of Aryl Sulfonates with sp2-Hybridized Nitrogen Nucleophiles: Palladium- and Nickel-catalyzed Synthesis of N-Aryl SulfoximinesSynthesis, 2000
- Highly Active and Selective Catalysts for the Formation of α-Aryl KetonesJournal of the American Chemical Society, 2000
- Highly Active Palladium Catalysts for Suzuki Coupling ReactionsJournal of the American Chemical Society, 1999
- Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998Journal of Organometallic Chemistry, 1999
- Sterically Hindered Chelating Alkyl Phosphines Provide Large Rate Accelerations in Palladium-Catalyzed Amination of Aryl Iodides, Bromides, and Chlorides, and the First Amination of Aryl TosylatesJournal of the American Chemical Society, 1998
- Aryl Mesylates in Metal Catalyzed Homocoupling and Cross-Coupling Reactions. 2. Suzuki-Type Nickel-Catalyzed Cross-Coupling of Aryl Arenesulfonates and Aryl Mesylates with Arylboronic AcidsThe Journal of Organic Chemistry, 1995