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Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate
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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.
Citing Articles
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones with Alkynylsilanols
Takahiro Nishimura, Sumito Tokuji, Takahiro Sawano and Tamio HayashiOrganic Letters2009 11 (15), 3222-3225Rhodium-Catalyzed Asymmetric Conjugate Alkynylation of Enones with Alkynylsilanols
Takahiro Nishimura, Sumito Tokuji, Takahiro Sawano and Tamio HayashiOrganic Letters2009 11 (15), 3222-3225Asymmetric conjugate alkynylation of α,β-unsaturated ketones with (triisopropylsilyl)ethynylsilanols giving β-alkynylketones took place in high yields with high enantioselectivity in the presence of chiral rhodium catalysts.
The Interplay of Invention, Discovery, Development, and Application in Organic Synthetic Methodology: A Case Study
Scott E. DenmarkThe Journal of Organic Chemistry2009 74 (8), 2915-2927The Interplay of Invention, Discovery, Development, and Application in Organic Synthetic Methodology: A Case Study
Scott E. DenmarkThe Journal of Organic Chemistry2009 74 (8), 2915-2927This Perspective chronicles the conceptual development, proof of principle, exploration of scope, mechanistic investigations, and applications in natural product total synthesis of palladium-catalyzed cross-coupling reactions of silicon derivatives. The ...
Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods
Scott E. Denmark and Christopher S. RegensAccounts of Chemical Research2008 41 (11), 1486-1499Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron- and Tin-Based Methods
Scott E. Denmark and Christopher S. RegensAccounts of Chemical Research2008 41 (11), 1486-1499In the panoply of modern synthetic methods for forming carbon−carbon and carbon−heteroatom bonds, the transition metal-catalyzed cross-coupling of organometallic nucleophiles with organic electrophiles enjoys a preeminent status. The preparative utility ...
Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
Scott E. Denmark, John D. Baird, and Christopher S. RegensThe Journal of Organic Chemistry2008 73 (4), 1440-1455Palladium-Catalyzed Cross-Coupling of Five-Membered Heterocyclic Silanolates
Scott E. Denmark, John D. Baird, and Christopher S. RegensThe Journal of Organic Chemistry2008 73 (4), 1440-1455The preparation of -rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the ...
One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers
Junghyun Chae, Jaesook Yun, and Stephen L. BuchwaldOrganic Letters2004 6 (26), 4809-4812One-Pot Sequential Cu-Catalyzed Reduction and Pd-Catalyzed Arylation of Silyl Enol Ethers
Junghyun Chae, Jaesook Yun, and Stephen L. BuchwaldOrganic Letters2004 6 (26), 4809-4812Enantiomerically enriched β-substituted diphenylsilyl enol ethers, which can be prepared from Cu-catalyzed asymmetric conjugate reduction, are utilized in the Pd-catalyzed arylation of various aryl bromides. This new method provides a simple route to α-...
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History
- Published In Issue November 14, 2003
- Received August 11, 2003
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