New Ligands for a General Palladium‐Catalyzed Amination of Aryl and Heteroaryl Chlorides
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- 15 June 2004
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 10 (12) , 2983-2990
- https://doi.org/10.1002/chem.200306026
Abstract
The synthesis and application of monodentate N-substituted heteroarylphosphines is described. In general, the ligands are conveniently prepared by selective metallation at the 2-position of the respective N-substituted heterocycle (pyrrole, indole) by using n-butyllithium/tetramethylethylenediamine (TMEDA) followed by quenching with dialkyl- or diarylchlorophosphines. Of the different ligands prepared, the new dialkyl-2-(N-arylindolyl)phosphines (cataCXium® P) perform excellently in the palladium-catalyzed amination of aryl and heteroaryl chlorides. Coupling of both activated and deactivated chloroarenes proceeds under mild conditions (room temperature to 60 °C). By using optimized conditions remarkable catalyst productivity (total turnover number, TON, up to 8000) and activity (turnover frequency, TOF=14 000 h−1 at 75 % conversion) are observed.Keywords
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