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

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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.

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

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Supplementary files

Article information


Submitted
14 Apr 2020
Accepted
27 Apr 2020
First published
27 Apr 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

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

M. Fischer and M. Schmidtmann, Chem. Commun., 2020, Advance Article , DOI: 10.1039/D0CC02626C

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