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An Immobilized‐Dirhodium Hollow‐Fiber Flow Reactor for Scalable and Sustainable C−H Functionalization in Continuous Flow
Author(s) -
Yoo ChunJae,
Rackl Daniel,
Liu Wenbin,
Hoyt Caroline B.,
Pimentel Brian,
Lively Ryan P.,
Davies Huw M. L.,
Jones Christopher W.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805528
Subject(s) - flow chemistry , diazo , surface modification , chemistry , microreactor , catalysis , regioselectivity , carbene , batch reactor , continuous reactor , cyclopropanation , combinatorial chemistry , chemical engineering , organic chemistry , engineering
A scalable flow reactor is demonstrated for enantioselective and regioselective rhodium carbene reactions (cyclopropanation and C−H functionalization) by developing cascade reaction methods employing a microfluidic flow reactor system containing immobilized dirhodium catalysts in conjunction with the flow synthesis of diazo compounds. This allows the utilization of the energetic diazo compounds in a safe manner and the recycling of the dirhodium catalysts multiple times. This approach is amenable to application in a bulk‐scale synthesis employing asymmetric C−H functionalization by stacking multiple fibers in one reactor module. The products from this sequential flow–flow reactor are compared with a conventional batch reactor or flow–batch reactor in terms of yield, regioselectivity, and enantioselectivity.