Rhodium-catalyzed regioselective decarboxylative hydroselenation and hydrothiolation of vinyl benzoxazinanones

Abstract

A rhodium(I)-catalyzed decarboxylative hydrochalcogenation of diverse vinyl benzoxazinanones is developed. The coupling of selenols or their surrogates with substrates provides allylic selenides with excellent linear- and E-selectivity, while the transformation of thiols delivers allylic sulfides with remarkable branch-selectivity. The broad substrate scope in combination with satisfactory functional group tolerance makes this protocol a new paradigm for regioselective hydrofunctionalization that involves reactive π-allylmetal species.