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Flow‐Based, Cerium Oxide Enhanced, Low‐Level Palladium Sonogashira and Heck Coupling Reactions by Perovskite Catalysts
Author(s) -
Battilocchio Claudio,
Bhawal Benjamin N.,
Chorghade Rajeev,
Deadman Benjamin J.,
Hawkins Joel M.,
Ley Steven V.
Publication year - 2014
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201300049
Subject(s) - chemistry , sonogashira coupling , catalysis , cerium oxide , palladium , cerium , solvent , perovskite (structure) , inorganic chemistry , chemical engineering , polymer chemistry , organic chemistry , engineering
A flow chemistry procedure for Sonogashira and Heck cross‐coupling reactions using a low‐level palladium perovskite catalyst (LaFe 0.95 Pd 0.05 O 3 ) deposited on cerium oxide is reported. The catalyst was generated in situ at high temperature using a flow platform. The system could be applied to a wide range of functionalised substrates, allowing clean and fast delivery of the products within a few minutes (10–30 min), after scavenging with thiourea polymer (QP‐TU) and sulfonic acid resin (QP‐SA). The use of an in‐line evaporator/solvent switching device allowed us to recover the solvent and transport the material into the following stage. The catalyst could be continuously used for at least 24 h, without any noticeable decrease in the catalytic efficiency. In one example the system was scaled to deliver 10 mmol of product.