Use of ferrocenic ligands associated to palladium for catalysed direct arylation of heteroarenes with aryl bromides or aryl chlorides

During this thesis, we studied the palladium-catalysed direct arylation of heteroarenes with aryl halides. Compared to the other more classical cross-couplings such as Suzuki, Negishi or Stille reactions, direct arylation is more attractive from both economical and ecological points of view. First, we demonstrated that ortho- and especially di-ortho-substituted aryl bromides can react nicely, with as little as 0.05 mol% catalyst loading. Many products were impossible to obtain with more classical reaction conditions. Then, we demonstrated that aryl chlorides can react at C2 or C5 positions of furans, thiophenes, pyrrole and thiazole, by using only 0,5 mol% of Pd(OAc)2 associate to a ferrocenyl ligand. Many different electron-poor aryl chlorides, usually non or poorly reactive, gave some very good results. Finally we demonstrated that, by using similar reaction conditions, the reaction can also occurred at C3 or C4 position of isoxazoles, benzofurans, indoles or pyrazoles.

Data and Resources

Additional Info

Field Value
Source https://theses.hal.science/tel-00793693
Author Roy, David
Maintainer CCSD
Last Updated May 14, 2026, 05:13 (UTC)
Created May 14, 2026, 05:13 (UTC)
Identifier NNT: 2012REN1S073
Language fr
Rights https://about.hal.science/hal-authorisation-v1/
contributor Institut des Sciences Chimiques de Rennes (ISCR) ; Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes) ; Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS)
creator Roy, David
date 2012-10-25T00:00:00
harvest_object_id 33786dda-e4c9-4535-9595-d3b3399babf5
harvest_source_id 3374d638-d20b-4672-ba96-a23232d55657
harvest_source_title test moissonnage SELUNE
metadata_modified 2025-08-12T00:00:00
set_spec type:THESE