A General Enantioselective C−H Arylation Using an Immobilized Recoverable Palladium Catalyst

Author:

Salameh Nihad12,Valentini Federica1,Baudoin Olivier2,Vaccaro Luigi1ORCID

Affiliation:

1. Laboratory of Green SOC, Dipartimento di Chimica, Biologia e Biotecnologie Università degli Studi di Perugia Via Elce di Sotto, 8 06124 Perugia Italy

2. Department of Chemistry University of Basel St. Johanns-Ring 19 CH-4056 Basel Switzerland

Abstract

AbstractWe herein report a general and efficient enantioselective C−H arylation of aryl bromides based on the use of BozPhos as the bisphosphine ligand and SP‐NHC‐PdII as recoverable heterogeneous catalyst. By exploiting the “release and catch” mechanism of action of the catalytic system, we used BozPhos as a broadly applicable chiral ligand, furnishing high enantioselectivities across all types of examined substrates containing methyl, cyclopropyl and aryl C−H bonds. For each reaction, the reaction scope was investigated, giving rise to 30 enantioenriched products, obtained with high yields and enantioselectivities, and minimal palladium leaching. The developed catalytic system provides a more sustainable solution compared to homogeneous systems for the synthesis of high added‐value chiral products through recycling of the precious metal.

Funder

Staatssekretariat für Bildung, Forschung und Innovation

Universität Basel

Publisher

Wiley

Subject

General Energy,General Materials Science,General Chemical Engineering,Environmental Chemistry

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