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Microwave‐Promoted Palladium(II)‐Catalyzed CP Bond Formation by Using Arylboronic Acids or Aryltrifluoroborates
Author(s) -
Andaloussi Mounir,
Lindh Jonas,
Sävmarker Jonas,
J. R. Sjöberg Per,
Larhed Mats
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901473
Subject(s) - chemistry , palladium , chemoselectivity , catalysis , aryl , ligand (biochemistry) , phosphonate , denticity , cationic polymerization , medicinal chemistry , organic chemistry , biochemistry , alkyl , receptor , crystal structure
The first Pd II ‐catalyzed P arylation has been performed by using palladium acetate, the rigid bidentate ligand dmphen (dmphen=2,9‐dimethyl‐1,10‐phenanthroline), and without the addition of base or acid. Couplings of arylboronic acids or aryl trifluoroborates with H‐phosphonate dialkyl esters were conducted in 30 min with controlled microwave (MW) heating under non‐inert conditions. Aryl phosphites were also synthesized at room temperature with atmospheric air as the sole reoxidant. The arylated phosphonates were isolated in 44–90 % yields. The excellent chemoselectivity of the method was illustrated in the synthesis of a Mycobacterium tuberculosis glutamine synthetase (MTB‐GS) inhibitor. Online ESIMS was used to detect cationic palladium species in ongoing reactions directly, and a catalytic cycle has been proposed based on these results.