3 years ago

Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes

Reaction of Dihalodiboranes(4) with a N-Heterocyclic Silylene: Facile Construction of 1-Aryl-2-Silyl-1,2-Diboraindanes
Dominic Prieschl, Andrea Deißenberger, Sunewang Rixin Wang, Holger Braunschweig, Thomas Kupfer, Rian D. Dewhurst, Alexander Hofmann, Annika Gackstatter, Tobias Brückner, Torsten Thiess, Annalena Gärtner
Dihalodiboranes(4) react with a N-heterocyclic silylene (NHSi) to generate NHSi adducts of 1-aryl-2-silyl-1,2-diboraindanes, as was confirmed by X-ray crystallography, featuring the functionalization of both B−X (X=halogen) bonds and a sp3- or sp2-C−H bond under mild conditions. Coordination of a third NHSi to the proposed 1,1-diaryl-2,2-disilyldiborane(4) intermediates, generated by a twofold B−X insertion, may be crucial for the C−H borylation that leads to the final products. Notably, our results demonstrate the first C−H borylation with a strong B−F bond activated by silylene insertion. A domino reaction of dihalodiborane(4) with three equivalents of N-heterocyclic silylene (NHSi) readily generated a NHSi adduct of 1-aryl-2-silyl-1,2-diboraindane and a HX insertion product (see scheme). The first C−H borylation with a strong B−F bond activated by silylene insertion was demonstrated by the analogous reaction of a difluorodiborane(4).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702377

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