Regioselective formal hydroamination of styrenes with 1-phenyl-1H-tetrazole-5-thiol.

ABSTRACT

1-Phenyl-1H-tetrazole-5-thiol 1 (PT-thiol) is employed in a unique Markovnikov-selective formal hydroamination of styrenyl compounds in the presence of catalytic amounts of Ga(OTf)3. This gives rise to the formation of tetrazolothione moieties in an atom-economical manner. Mechanistically, we have determined that this transformation may occur by kinetically favored hydrothiolation, followed by rearrangement to the observed hydroamination products.