AI Article Synopsis
- The study demonstrates that encapsulating copper in a cyclodextrin with an N-heterocyclic carbene enhances its ability to capture monomeric (L)CuH and perform selective chemical reactions.
- The specific structure of the cyclodextrin (α or β) influences the type of reaction product formed: α-ICyD leads to a 1,2-addition, while β-ICyD results in a fully reduced product.
- The variation in chemoselectivity is attributed to the cyclodextrin's cavity size and the weaker interactions between the substrate and the internal C-H bonds of the cyclodextrin.
Article 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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| http://dx.doi.org/10.1002/anie.202001733 | DOI Listing |
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Capturing the Monomeric (L)CuH in NHC-Capped Cyclodextrin: Cavity-Controlled Chemoselective Hydrosilylation of α,β-Unsaturated Ketones.
Angew Chem Int Ed Engl
May 2020
Sorbonne Université, CNRS, Institut Parisien de Chimie Moléculaire (IPCM), UMR 8232, 4, place Jussieu, 75005, Paris, France.
Article Synopsis
- The study demonstrates that encapsulating copper in a cyclodextrin with an N-heterocyclic carbene enhances its ability to capture monomeric (L)CuH and perform selective chemical reactions.
- The specific structure of the cyclodextrin (α or β) influences the type of reaction product formed: α-ICyD leads to a 1,2-addition, while β-ICyD results in a fully reduced product.
- The variation in chemoselectivity is attributed to the cyclodextrin's cavity size and the weaker interactions between the substrate and the internal C-H bonds of the cyclodextrin.
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