Efficient and General Synthesis of 5-(Alkoxycarbonyl)methylene-3-oxazolines by Palladium-Catalyzed Oxidative Carbonylation of Prop-2-ynylamides
Citations Over TimeTop 10% of 2002 papers
Abstract
A variety of prop-2-ynylamides have been carbonylated under oxidative conditions to give oxazolines, oxazolines with chelating groups, and bisoxazolines bearing an (alkoxycarbonyl)methylene chain at the 5 position in good yields. The cyclization-alkoxycarbonylation process was carried out in alcoholic media at 50-70 degrees C and under 24 bar pressure of 3:1 carbon monoxide/air in the presence of catalytic amounts of 10% Pd/C or PdI2 in conjunction with KI. Cyclization occurred by anti attack of an oxygen function on the palladium-coordinated triple bond, followed by stereospecific alkoxycarbonylation, strictly resulting in E-stereochemistry. The structures of representative oxazolines and bisoxazolines have been determined by X-ray diffraction analysis.
Related Papers
- → Preparation of organo palladium sols from palladium complexes in various alcohols(1994)32 cited
- → The constitution of cerium-palladium alloys containing 50–100% palladium(1967)48 cited
- → Allyl(β‐diketonato)palladium(II) complexes as precursors for palladium films(1994)36 cited
- → Reduction of palladium(II) monoglycinate complexes at rotating disc palladium electrode in acid media(2010)1 cited
- Rapid Determination of Palladium in Palladium-Nickel and Palladium-Cobalt Plating Bath(2003)