Catalyst-controlled divergent transformations of N-sulfonyl-1,2,3-triazoles into isoquinolin-3-ones and 2-aminoindanones

Abstract

Novel catalyst-controlled divergent intramolecular reactions of N-sulfonyl-1,2,3-triazoles with tethered-allylic alcohol have been developed. In the presence of the Pd(0) catalyst alone, 1-vinylated 1,4-dihydroisoquinolin-3-ones were formed, whereas 3-vinylated 2-aminoindanones were accessed under tandem, one-pot, Rh(II)/Pd(0) dual catalytic conditions. Based on deuterium-labelling experiments and isolation of the intermediate, a plausible reaction mechanism has been proposed.