Allenyl Thianthrenium Salt: A Bench-Stable C<sub>3</sub> Synthon for Annulation and Cross-Coupling Reactions
Srija Tewari, Nicolai Klask, Tobias Ritter
Abstract
High Resolution Image Download MS PowerPoint Slide Herein, we report the first bench-stable and nonhygroscopic monosubstituted allenyl sulfonium salt (ATT) synthesized from thianthrene and propargyl alcohol. We demonstrate its use in annulation chemistry to synthesize heterocycles, such as 2-hydroxy morpholine, 2-methyl quinoxalines, and benzodioxepinone derivatives, with an exocyclic double bond. The reagent is the first allenyl sulfonium salt that can undergo palladium-catalyzed cross-coupling reactions to form a C(sp 2 )–C(sp 2 ) bond via Suzuki coupling and a C(sp 3 )–C(sp 2 ) bond formation via reductive coupling.
Topics & Concepts
ChemistrySynthonAnnulationSalt (chemistry)Coupling (piping)Coupling reactionComputational chemistryStereochemistryOrganic chemistryCatalysisEngineeringMechanical engineeringCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms