Tungsten-Catalyzed Allylic Substitution with a Heteroatom Nucleophile: Reaction Development and Synthetic Applications
Yaoyao Xu, Muhammad Salman, Shahid Khan, Junjie Zhang, Ajmal Khan
Abstract
A tungsten-catalyzed allylic allylation of sodium sulfinate as the heteroatom nucleophile was developed. The reaction utilizes inexpensive and readily available (CH3CN)3W(CO)3 as a precatalyst and proceeds at 60 °C temperature in the presence of 2,2′-bipyridine and its derivatives as ligand. The synthetic utility of allylic sulfones as electrophile was further demonstrated through Suzuki–Miyaura cross-coupling as showcased by the formal synthesis of (±)-hinokiresinol.
Topics & Concepts
ChemistryAllylic rearrangementHeteroatomSubstitution reactionCatalysisTungstenSubstitution (logic)NucleophileNucleophilic substitutionCombinatorial chemistryOrganic chemistryMedicinal chemistryRing (chemistry)Computer scienceProgramming languageAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques