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Application of Cyclodextrin-N-heterocyclic Carbene Complexes in Catalysis

Abstract : Cyclodextrin (CD)-N-heterocyclic carbene (NHC)-copper complexes, (α/β-ICyD)BnCuCl, previously developed by our group, were used as catalysts in carboboration of alkynes. The (α/β-ICyD)BnCuCl both gave the linear (L) (E)-vinyl boron isomers with high regioselectivity in the copper-catalyzed methyl boration of terminal alkynes. Furthermore, the intramolecular carboboration reaction with terminal alkynes functionalized by alkyl halides, (α/β-ICyD)BnCuCl both led to exocyclic vinyl boronate species as the major isomer, and an unexpected endocyclic (Z)-isomer was also observed.We have developed two novel bis(azolium)-precursors, with one azolium moiety inside the cavity of α-CD, and another one outside the cavity. These two azolium moieties are connected by an ethynyl or phenyl linker. Taking advantage of the steric hindrance of the α-CD cavity, a series of mono-, homo- and heterobimetallic complexes were developed, including AgI, CuI, AuI, AuIII, and PdII species. The electrochemical properties of corresponding Cu and Au complexes were investigated by cyclic voltammetry. And the electronic absorption properties of all complexes and precursors were studied by ultraviolet−visible (UV-Vis) spectroscopy.
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Submitted on : Tuesday, July 19, 2022 - 1:36:37 PM
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  • HAL Id : tel-03727569, version 1


Zhonghang Wen. Application of Cyclodextrin-N-heterocyclic Carbene Complexes in Catalysis. Organic chemistry. Sorbonne Université, 2021. English. ⟨NNT : 2021SORUS428⟩. ⟨tel-03727569⟩



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