The chemistry of carbene-borane and carbene-silane complexes – NHCX

Our research uses the tools and methods of organic chemistry, photochemistry and polymer chemistry

not applicable at that stage

This project seeks to introduce non toxic reagents for organic and polymer synthesis that are derived from abundant sources

3 publications
1) «[3+2]-Dipolar cycloaddition reactions of an N-heterocyclic carbene boryl azide« Merling, E.; Lamm, V.; Geib, S. J.; Lacôte, E.; Curran D. P. Org. Lett. 2012, 14, 2690-2693;

2) «Polarity Reversal Catalysis in Radical Reductions of Halides by N-Heterocyclic Carbene Boranes« Pan, X.; Lacôte, E.; Lalevée, J.; Curran, D. P. J. Am. Chem. Soc. 2012, 134, 5669-5674.

3) «Reactions of boron-substituted N-heterocyclic carbene boranes with triflic acid. Isolation of a new dihydroxyborenium cation« Solovyev, A.; Geib, S. J.; Lacôte, E.; Curran, D. P. Organometallics 2012, 31, 54-56.

The objective of the present proposal is to significantly expand the chemistry of carbene-main group element complexes toward generating new reagents and catalysts for organic chemistry.

• We will strengthen our understanding of NHC-boron chemistry. It offers still unsolved challenges, such as the hydroboration. Likewise, the ionic and organometallic chemistries have only been cursorily studied and a deeper examination is warranted. Research will also focus on other classes of carbene and carbene-analogs that could be employed to complex boron.

• There are scattered reports on NHC-Silicon chemistry. However again, no general analysis of this reactivity has been offered. We wish to approach this issue much more deeply. We surmise that the one periodic table-column shift, combined with the possibility for Si to go hypervalent might allow catalytic organic processes.

• Finally, silaboranes are derivatives which combine both elements. It is important to examine their reactivity toward carbenes, and determine whether the single reactivities of both elements can be also combined to generate new reactions.