Capturing the Monomeric (L)CuH in NHC‐Capped Cyclodextrin: Cavity‐Controlled Chemoselective Hydrosilylation of α,β‐Unsaturated Ketones
(2020) Angewandte Chemie (International Edition) — Vol. 59, n° 19, p. 7591-7597 (2020)
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Sollogoub, Matthieu 
- Abstract
- The encapsulation of copper inside a cyclodextrin capped with an N ‐heterocyclic carbene (ICyD) allowed both to catch the elusive monomeric (L)CuH and a cavity‐controlled chemoselective copper‐catalyzed hydrosilylation of α,β‐unsaturated ketones. Remarkably, (α‐ICyD)CuCl promoted the 1,2‐addition exclusively, while (β‐ICyD)CuCl produced the fully reduced product. The chemoselectivity is controlled by the size of the cavity and weak interactions between the substrate and internal C−H bonds of the cyclodextrin.
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Citations
Xu, G., Leloux, S., Zhang, P., Meijide Suárez, J., Zhang, Y., Derat, E., Ménand, M., Bistri‐Aslanoff, O., Roland, S., Leyssens, T., Riant, O., & Sollogoub, M. (2020). Capturing the Monomeric (L)CuH in NHC‐Capped Cyclodextrin: Cavity‐Controlled Chemoselective Hydrosilylation of α,β‐Unsaturated Ketones. Angewandte Chemie (International Edition), 59(19), 7591-7597. https://doi.org/10.1002/anie.202001733 (Original work published 2020)