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C(sp 3 )−H Arylation Promoted by a Heterogeneous Palladium‐N‐Heterocyclic Carbene Complex in Batch and Continuous Flow
Author(s) -
Ferlin Francesco,
Anastasiou Ioannis,
Salameh Nihad,
Miyakoshi Takeru,
Baudoin Olivier,
Vaccaro Luigi
Publication year - 2022
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202102736
Subject(s) - carbene , catalysis , palladium , chemistry , intramolecular force , iodide , polystyrene , ligand (biochemistry) , heterogeneous catalysis , combinatorial chemistry , continuous flow , organic chemistry , biochemistry , receptor , polymer , physics , mechanics
A heterogeneous reusable palladium(II)‐bis(N‐heterocyclic carbene) catalyst was prepared and shown to catalyze the intramolecular C(sp 3 )−H activation/cyclization of N ‐alkyl‐2‐bromoanilines furnishing indolines. This new catalytic system was based on a bis‐imidazolium ligand immobilized on a spaced cross‐linked polystyrene support. The iodide ligands on the catalyst played a central role in the efficiency of the process occurring through a “release and catch” mechanism. The heterogeneous nature of the catalyst was further exploited in the design of a continuous‐flow protocol that allowed a more efficient recovery and reuse of the catalyst, as well as a very fast and safe procedure.