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Combining Ru-Catalyzed C-H Functionalization with Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of 3-Allyl-3-aryl Oxindole Derivatives from Aryl α-Diazoamides.
- Kosuke Yamamoto, Zafar Qureshi, J. Tsoung, Guillaume Pisella, M. Lautens
- Chemistry, BiologyOrganic Letters
- 15 September 2016
The novel dual-metal-catalyzed reaction provides a variety of 3-allyl-3-aryl oxindoles from the corresponding α-diazoamides in up to 99% yield with up to 85% ee.
Copper-Catalyzed Oxyvinylation of Diazo Compounds.
A copper(I)-catalyzed vinylation of diazo compounds with vinylbenziodoxolone reagents (VBX) as partners is reported. The transformation tolerates diverse functionalities on both reagents delivering…
Copper-Catalyzed Oxyalkynylation of C-S Bonds in Thiiranes and Thiethanes with Hypervalent Iodine Reagents.
The oxyalkynylation of thiiranes and thietanes is reported using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group with high atom efficiency.
Vinylbenziodoxol(on)es: Synthetic Methods and Applications
Three-Component Reaction for the Synthesis of Highly Functionalized Propargyl Ethers.
A copper-catalyzed three-component reaction of diazo compounds, alcohols and ethynyl benziodoxole (EBX) reagents for the synthesis of propargyl ethers is reported, leading to highly functionalized and structurally diverse products under mild conditions.
Copper-Catalyzed Insertion of Diazo Compounds into Vinyl Hypervalent Iodine Reagents to Generate Allylic Esters
An unprecedented copper(I)-catalyzed vinylation of (donor)-acceptor diazo compounds with VinylBenziodoXolone reagents (VBX) as partners is reported, delivering the corresponding benzoylated allylic alcohol products in good to excellent yields.
Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines.
The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by a simple Cu(I) salt is described, which allows the synthesis of propargylic amines with broad functional group tolerance.
Low-Temperature Intramolecular [4+2] Cycloaddition of Allenes with Arenes for the Synthesis of Diene Ligands.
A one-pot oxyalkynylation/cycloaddition reaction proceeding under mild conditions and providing complex polycyclic architectures with high efficiency, atom and step economy and a first rationalization of the low activation energy for the cycloadditions based on counter-intuitive favorable dispersive interactions in the transition state.
New Vinylation and Alkynylation Strategies with Hypervalent Iodine Reagents and Diazo Compounds
- Guillaume Pisella