(3 + 2)-Cycloaddition of Donor–Acceptor Cyclopropanes with Selenocyanate: Synthesis of Dihydroselenophenes and Selenophenes
Anu Jacob, Peter G. Jones, Daniel B. Werz
Abstract
We present a Lewis-acid-catalyzed (3 + 2)-cycloaddition of donor-acceptor cyclopropanes and selenocyanate (as its tetramethylammonium salt) for the synthesis of dihydroselenophenes. The transformation proceeded with moderate to excellent yields and showed a high functional group tolerance. Further oxidation using DDQ delivered selenophenes.
Topics & Concepts
ChemistryCycloadditionAcceptorTetramethylammoniumLewis acids and basesSalt (chemistry)Combinatorial chemistryStereochemistryMedicinal chemistryCatalysisOrganic chemistryIonCondensed matter physicsPhysicsCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsSulfur-Based Synthesis Techniques