Baylis–Hillman adducts in rhodium-catalyzed 1,4-additions: unusual reactivity
- 5 April 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- Vol. 35 (9) , 1108-1109
- https://doi.org/10.1039/b402928c
Abstract
In the presence of a rhodium catalyst, unactivated Baylis–Hillman adducts reacted with arylboronic acids to afford trisubstituted alkenes with good yields. This highly efficient reaction (aerobic conditions, low temperature) is believed to proceeds via an unexpected mechanism involving 1,4-addition/β-hydroxy elimination steps and not π-allyl type rhodium intermediates.Keywords
This publication has 35 references indexed in Scilit:
- Tandem 1,4‐Addition/Enantioselective Protonation Catalyzed by Rhodium Complexes: Efficient Access to α‐Amino AcidsAngewandte Chemie International Edition in English, 2004
- Efficient Access to Alanine Derivatives by 1,4‐Additions of Potassium Trifluoro(organo)boratesEuropean Journal of Organic Chemistry, 2003
- Novel Synthesis of Benzenepolycarboxylates by Ruthenium-Catalyzed Cross-Benzannulation of Acetylenedicarboxylates with Allylic CompoundsOrganometallics, 2002
- A Novel Palladium Catalyst for Cross-Coupling of Allyl Acetates with Arylboronic AcidsEuropean Journal of Organic Chemistry, 2002
- Ruthenium-Catalyzed Cyclopropanation of Norbornene with Propargyl AlcoholBulletin of the Chemical Society of Japan, 1999
- RuCl2(PPh3)3Catalyzed Isomerization of the Baylis-Hillman AdductsSynthetic Communications, 1999
- Applications of the Baylis–Hillman reaction 2: a simple stereoselective synthesis of (E)- and (Z)-trisubstituted alkenesJournal of the Chemical Society, Chemical Communications, 1994
- Synthesis of Optically Active Substituted Dihydrofurans and Dihydropyrroles via Palladium (II)-Promoted Diastereoselective Dehydroxylative HeterocyclizationSynlett, 1992
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Palladium(II)-catalyzed exchange and isomerization reactions. 13. Palladium(II) chloride catalyzed exchange and isomerization of 2-(methyl-d3)-4-methyl-3-penten-2-ol and its ethyl ether in methanolOrganometallics, 1991