Reaction monitoring reveals poisoning mechanism of Pd2(dba)3 and guides catalyst selection.

Author(s) Colletto, C.; Burés, J.; Larrosa, I.
Journal Chem Commun (Camb)
Date Published 2017 Nov 30
Abstract

We have discovered that the dba ligand in the commonly used Pd(dba)·CHCl cross-coupling pre-catalyst is susceptible to bis-arylation when used in the presence of aryl iodides. The in situ formed dbaAr ligands result in Pd-species with altered catalytic activity. In the case of study, the room temperature C3 arylation of benzo[b]thiophenes with aryl iodides, we have observed a marked catalyst deactivation when dba is arylated with electron-deficient aryl iodides, accounting for the poor yields obtained in the C3 arylation reactions with these aryl iodides. Based on these studies, we report a new catalytic system, employing a dba-free Pd catalyst, which allows for the first time the direct C3 arylation of benzo[b]thiophenes with electron-deficient aryl iodides at room temperature.

DOI 10.1039/c7cc08018b
ISSN 1364-548X
Citation Colletto C, Burés J, Larrosa I. Reaction monitoring reveals poisoning mechanism of Pd2(dba)3 and guides catalyst selection. Chem Commun (Camb). 2017;53(96):12890-12893.

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