Pd-Catalyzed Cross-Coupling of Highly Sterically Congested Enol Carbamates with Grignard Reagents via C–O Bond Activation
Zicong Chen, Chau Ming So
Abstract
The palladium-catalyzed cross-coupling reaction of enol carbamates to construct highly sterically congested alkenyl compounds is presented for the first time. This protocol demonstrates the potential of using thermally stable and highly atom-economic enol electrophiles as building blocks in bulky alkene synthesis. This reaction accommodates a broad substrate scope with excellent Z/E isomer ratios, which also provides a new synthetic pathway for accessing Tamoxifen.
Topics & Concepts
ChemistryEnolSteric effectsElectrophileAlkeneCatalysisCombinatorial chemistrySubstrate (aquarium)Coupling reactionPalladiumMedicinal chemistryStereochemistryOrganic chemistryOceanographyGeologyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCarbon dioxide utilization in catalysis