Palladium-Catalyzed α-Vinylation of Carbonyl Compounds
- 22 September 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (21) , 4343-4346
- https://doi.org/10.1021/ol7019839
Abstract
A mild, general, catalytic system for the alpha-vinylation of carbonyl compounds has been developed. By employing [Pd(P(t)Bu(3))Br](2) as catalyst and LHMDS as base, vinyl bromides, vinyl triflates, and vinyl tosylates couple with 3-methyloxindole in satisfactory yields. The same catalytic system is extended to the alpha-vinylation of ketones and esters.Keywords
This publication has 33 references indexed in Scilit:
- Efficient Palladium-Catalysed Enamide Synthesis from Enol Triflates and Enol TosylatesSynthesis, 2005
- Palladium-Catalyzed Synthesis of N-Vinyl Pyrroles and IndolesThe Journal of Organic Chemistry, 2005
- Palladium-Catalyzed α-Arylation of Carbonyl Compounds and NitrilesAccounts of Chemical Research, 2003
- Efficient Synthesis of α-Aryl Esters by Room-Temperature Palladium-Catalyzed Coupling of Aryl Halides with Ester EnolatesJournal of the American Chemical Society, 2002
- Palladium-Catalyzed Intramolecular α-Arylation of α-Amino Acid EstersThe Journal of Organic Chemistry, 2001
- Simple indole alkaloids and those with a nonrearranged monoterpenoid unitNatural Product Reports, 2001
- Palladium-Catalyzed α-Arylation of Esters and Protected Amino AcidsJournal of the American Chemical Society, 2001
- Improved Catalysts for the Palladium-Catalyzed Synthesis of Oxindoles by Amide α-Arylation. Rate Acceleration, Use of Aryl Chloride Substrates, and a New Carbene Ligand for Asymmetric TransformationsThe Journal of Organic Chemistry, 2001
- Palladium-Catalyzed α-Arylation of KetonesJournal of the American Chemical Society, 1997
- Palladium‐Catalyzed Regioselective Mono‐ and Diarylation Reactions of 2‐Phenylphenols and Naphthols with Aryl HalidesAngewandte Chemie International Edition in English, 1997