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Cyclodextrin Cavity‐Induced Mechanistic Switch in Copper‐Catalyzed Hydroboration
Author(s) -
Zhang Pinglu,
Meijide Suárez Jorge,
Driant Thomas,
Derat Etienne,
Zhang Yongmin,
Ménand Mickaël,
Roland Sylvain,
Sollogoub Matthieu
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705303
Subject(s) - hydroboration , cyclodextrin , regioselectivity , chemistry , selectivity , catalysis , copper , carbene , combinatorial chemistry , stereochemistry , organic chemistry
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.