Cyclodextrin Cavity‐Induced Mechanistic Switch in Copper‐Catalyzed Hydroboration. (2nd August 2017)

• Record Type: Journal Article
• Authors: Zhang, Pinglu; Meijide Suárez, Jorge; Driant, Thomas; Derat, Etienne; Zhang, Yongmin; Ménand, Mickaël; Roland, Sylvain; Sollogoub, Matthieu
• Is Part Of: Angewandte Chemie. Volume 129:Number 36(2017)
• Page Start: 10961
• Page End: 10965
• Publication Date: 2017-08-02
• Subjects: Katalyse -- Kupfer -- Cyclodextrine -- Regioselektivität -- Supramolekulare Chemie; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201705303
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: N ‐heterocyclic carbene‐capped cyclodextrin (ICyD) ligands, α‐ICyD and β‐ICyD derived from α‐ and β‐cyclodextrin, respectively give opposite regioselectivities in a copper‐catalyzed hydroboration. The site‐selectivity results from two different mechanisms: the conventional parallel one and a new orthogonal mechanism. The shape of the cavity was shown not only to induce a regioselectivity switch but also a mechanistic switch. The scope of interest of the encapsulation of a reactive center is therefore broadened by this study.