Catalytic Intermolecular Ortho-Arylation of Phenols
- 1 October 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (22) , 8669-8682
- https://doi.org/10.1021/jo030157k
Abstract
The use of rhodium catalysts such as [RhCl(PPh3)3] or [[RhCl(COD)]2] with PiPr2(OAr) or P(NMe2)3 co-catalysts allows the ortho-selective intermolecular arylation of phenols. The reaction proceeds via orthometalation of P-OAr groups and then transesterification liberates the product phenol. When 2-substituted phenols are used as substrates, [RhCl(PPh3)3]/iPr2(OAr) mixtures are typically the catalysts of choice, whereas for substrates without 2-substitution [[RhCl(COD)]2]/P(NMe2)3 mixtures tend to give better results.Keywords
This publication has 22 references indexed in Scilit:
- Orthopalladated and ‐platinated Bulky Triarylphosphite Complexes: Synthesis, Reactivity and Application as High‐Activity Catalysts for Suzuki and Stille Coupling ReactionsChemistry – A European Journal, 2003
- The Role of Ligand Transformations on the Performance of Phosphite- and Phosphinite-Based Palladium Catalysts in the Suzuki ReactionOrganometallics, 2003
- Platinum Catalysts for Suzuki Biaryl Coupling ReactionsOrganometallics, 2002
- Palladacyclic phosphinite complexes as extremely high activity catalysts in the Suzuki reactionChemical Communications, 2000
- Asymmetric Coupling of Phenols with ArylleadsJournal of the American Chemical Society, 1999
- Orthopalladated triaryl phosphite complexes as highly active catalysts in biaryl coupling reactionsChemical Communications, 1998
- Palladium‐Catalyzed Regioselective Mono‐ and Diarylation Reactions of 2‐Phenylphenols and Naphthols with Aryl HalidesAngewandte Chemie International Edition in English, 1997
- Anion-Accelerated Palladium-Catalyzed Intramolecular Coupling of Phenols with Aryl HalidesThe Journal of Organic Chemistry, 1997
- Iridium Complexes of Orthometalated Triaryl Phosphites: Synthesis, Structure, Reactivity, and Use as Imine Hydrogenation CatalystsOrganometallics, 1996
- Reexamination of the deuteration of phenol catalyzed by an orthometalated ruthenium complexInorganic Chemistry, 1985