Tandem Olefin Isomerization/Cyclization Catalyzed by Complex Nickel Hydride and Brønsted Acid

J Org Chem. 2020 Dec 4;85(23):15183-15196. doi: 10.1021/acs.joc.0c02033. Epub 2020 Nov 11.

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.