Stereospecific Palladium-Catalyzed Cross-Coupling of (E)- and (Z)-Alkenylsilanolates with Aryl Chlorides
- 1 December 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (50) , 15958-15959
- https://doi.org/10.1021/ja065988x
Abstract
The cross-coupling of geometrically defined (E)- and (Z)-alkenyl- and styrylsilanolates with a wide variety of aromatic and heteroaromatic chlorides has been achieved. Under catalysis by bulky, biphenyl-derived phosphines and allylpalladium chloride, the (preformed, stable) potassium salts of di-, tri- and tetrasubstituted alkenyldimethylsilanols undergo high yielding and highly stereospecific coupling to aryl chlorides in THF or dioxane. A variety of functional groups are compatible with these reaction conditions including nitro, ester, ketone, and nitrile. Both (E)- and (Z)-alkenylsilanolates coupled with nearly identical rate and efficiency.Keywords
This publication has 15 references indexed in Scilit:
- Palladium‐Catalyzed Cross‐Coupling Reactions of Silanolates: A Paradigm Shift in Silicon‐Based Cross‐Coupling ReactionsChemistry – A European Journal, 2006
- Oxidative Addition of Hydrogen Halides and Dihalogens to Pd. Trends in Reactivity and Relativistic EffectsThe Journal of Physical Chemistry A, 2006
- A Highly Active Catalyst for Suzuki–Miyaura Cross‐Coupling Reactions of Heteroaryl CompoundsAngewandte Chemie International Edition in English, 2006
- Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig ReactionsJournal of the American Chemical Society, 2006
- Dynamic Kinetic Resolution of α,β‐Unsaturated Lactones through Asymmetric Copper‐Catalyzed Conjugate Reduction: Application to the Total Synthesis of Eupomatilone‐3Angewandte Chemie International Edition in English, 2005
- Catalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand StructureJournal of the American Chemical Society, 2005
- Cross‐Coupling of Triallyl(aryl)silanes with Aryl Bromides and Chlorides: An Alternative Convenient Biaryl SynthesisAdvanced Synthesis & Catalysis, 2004
- Palladium-Catalyzed Coupling Reactions of Aryl ChloridesAngewandte Chemie International Edition in English, 2002
- Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild ConditionsJournal of the American Chemical Society, 2000
- Cross-Coupling Reactions of Aryl Chlorides with Organochlorosilanes: Highly Effective Methods for Arylation or Alkenylation of Aryl ChloridesThe Journal of Organic Chemistry, 1996