Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Brønsted Acid
Prasad Kathe, Alexandru Căciuleanu, Andreas Berkefeld, Ivana Fleischer
Abstract
We disclose a nickel/Brønsted acid-catalyzed tandem process consisting of double bond isomerization of allyl ethers and amines and subsequent intramolecular reaction with nucleophiles. The process is accomplished by [(Me3P)4NiH]N(SO2CF3)2 in the presence of triflic acid. The methodology provides rapid access to tetrahydropyran-fused indoles and other oxacyclic scaffolds under very low catalyst loadings.
Topics & Concepts
ChemistryIsomerizationCatalysisTandemTriflic acidBrønsted–Lowry acid–base theoryIntramolecular forceOlefin fiberNucleophileNickelHydrideCombinatorial chemistryDouble bondCascade reactionMedicinal chemistryOrganic chemistryHydrogenComposite materialMaterials scienceSynthetic Organic Chemistry MethodsAsymmetric Synthesis and CatalysisCatalytic C–H Functionalization Methods