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Issue 96, 2017
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Reaction monitoring reveals poisoning mechanism of Pd2(dba)3 and guides catalyst selection

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Abstract

We have discovered that the dba ligand in the commonly used Pd2(dba)3·CHCl3 cross-coupling pre-catalyst is susceptible to bis-arylation when used in the presence of aryl iodides. The in situ formed dbaAr2 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.

Graphical abstract: Reaction monitoring reveals poisoning mechanism of Pd2(dba)3 and guides catalyst selection

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Supplementary files

Article information


Submitted
17 Oct 2017
Accepted
06 Nov 2017
First published
16 Nov 2017

Chem. Commun., 2017,53, 12890-12893
Article type
Communication

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

C. Colletto, J. Burés and I. Larrosa, Chem. Commun., 2017, 53, 12890
DOI: 10.1039/C7CC08018B

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