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Optimized Immobilization Strategy for Dirhodium(II) Carboxylate Catalysts for C−H Functionalization and Their Implementation in a Packed Bed Flow Reactor
Author(s) -
Hatridge Taylor A.,
Liu Wenbin,
Yoo ChunJae,
Davies Huw M. L.,
Jones Christopher W.
Publication year - 2020
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.202005381
Subject(s) - catalysis , packed bed , chemistry , heterogeneous catalysis , surface modification , stereoselectivity , chemical engineering , homogeneous , flow chemistry , combinatorial chemistry , chromatography , organic chemistry , thermodynamics , physics , engineering
Abstract Herein we demonstrate a packed bed flow reactor capable of achieving highly regio‐ and stereoselective C−H functionalization reactions using a newly developed Rh 2 ( S ‐2‐Cl‐5‐CF 3 TPCP) 4 catalyst. To optimize the immobilized dirhodium catalyst employed in the flow reactor, we systematically study both (i) the effects of ligand immobilization position, demonstrating the critical factor that the catalyst‐support attachment location can have on the catalyst performance, and (ii) silica support mesopore length, demonstrating that decreasing diffusional limitations leads to increased accessibility of the active site and higher catalyst turnover frequency. We employ the immobilized dirhodium catalyst in a simple packed bed flow reactor achieving comparable yields and levels of enantioselectivity to the homogeneous catalyst employed in batch and maintain this performance over ten catalyst recycles.