Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate
- 23 October 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (23), 9151-9154
- https://doi.org/10.1021/jo0351771
Abstract
The palladium-catalyzed cross-coupling of aliphatic alkynylsilanols with aryl iodides has been demonstrated with potassium trimethylsilanolate as the coupling promoter and copper(I) iodide as a cocatalyst. The cross-coupling proceeds at room temperature in good to excellent yield with a range of aryl iodides. A comparison of the reactivity of alkynylsilanols, trimethylsilylalkynes, and terminal alkynes under fluoride and fluoride-free conditions was performed to elucidate the role of silicon in the Sonogashira reaction.Keywords
This publication has 29 references indexed in Scilit:
- Palladium-Catalyzed AlkynylationChemical Reviews, 2003
- Highly Selective and Practical Hydrolytic Oxidation of Organosilanes to Silanols Catalyzed by a Ruthenium ComplexJournal of the American Chemical Society, 2000
- Palladium-Catalyzed Cross-Coupling of Silanols, Silanediols, and Silanetriols Promoted by Silver(I) OxideThe Journal of Organic Chemistry, 2000
- Coupling Reactions of Alkynylsilanes Mediated by a Cu(I) Salt: Novel Syntheses of Conjugate Diynes and Disubstituted EthynesThe Journal of Organic Chemistry, 2000
- A Facile Preparation and Cyclopropanation of 1-AlkenylsilanolsBulletin of the Chemical Society of Japan, 1998
- Palladium-Catalyzed Cross-Coupling Reactions of Organoboron CompoundsChemical Reviews, 1995
- Silanol synthesis: reaction of hexaphenylcyclotrisiloxane with organometallic reagentsThe Journal of Organic Chemistry, 1993
- Stereospecific palladium-catalyzed coupling reactions of vinyl iodides with acetylenic tin reagentsJournal of the American Chemical Society, 1987
- The Palladium‐Catalyzed Cross‐Coupling Reactions of Organotin Reagents with Organic Electrophiles [New Synthetic Methods (58)]Angewandte Chemie-International Edition, 1986
- Highly general stereo-, regio-, and chemo-selective synthesis of terminal and internal conjugated enynes by the Pd-catalysed reaction of alkynylzinc reagents with alkenyl halidesJournal of the Chemical Society, Chemical Communications, 1977