Issue 96, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
17 Okt 2017
Accepted
06 Nov 2017
First published
16 Nov 2017

Chem. Commun., 2017,53, 12890-12893

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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