B(C6F5)3- and HB(C6F5)2-mediated transformations of isothiocyanates

Abstract

This contribution reports on the reactivity of isothiocyanates towards the boranes B(C₆F₅)₃ and HB(C₆F₅)₂. The reactions of alkyl-substituted isothiocyanates with B(C₆F₅)₃ were found to result in rearrangement reactions to yield stable thiocyanate–B(C₆F₅)₃ adducts. Treatment of isothiocyanates with HB(C₆F₅)₂ leads to 1,2-hydroboration and thus, B,N,C,S heterocycles are formed, which react further under non-inert conditions. Hydrolysis of the hydroboration products leads to a new access to thioformamides.