Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System

Diana Lamaa; Estelle Messe; Vincent Gandon; Mouad Alami; Abdallah Hamze

doi:10.1021/acs.orglett.9b03310

Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H₂O Recyclable Catalytic System

Org Lett. 2019 Nov 1;21(21):8708-8712. doi: 10.1021/acs.orglett.9b03310. Epub 2019 Oct 16.

Authors

Diana Lamaa¹, Estelle Messe¹, Vincent Gandon², Mouad Alami¹, Abdallah Hamze¹

Affiliations

¹ BioCIS UMR 8076 , Université Paris-Sud, CNRS, Université Paris-Saclay, Equipe Labellisée Ligue Contre Le Cancer, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie , rue J.-B. Clément , F-92296 Châtenay-Malabry , France.
² Institut de Chimie Moleculaire et des Matériaux d'Orsay (ICMMO), CNRS UMR 8182 , Université Paris-Sud, Université Paris-Saclay , Batiment 420 , 91405 Orsay Cedex , France.

PMID: 31618043
DOI: 10.1021/acs.orglett.9b03310

Abstract

A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO₃Na or Pd/MeDavephos-CF₃SO₃ in PEG/H₂O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.

Publication types

Research Support, Non-U.S. Gov't