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Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
Chemistry. 2009 Dec 07; 15(47):13069-74.C

Abstract

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.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Andaloussi M
Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry, Uppsala University, BMC, Box-574, 751 23 Uppsala, Sweden.
Lindh J
No affiliation info available
Sävmarker J
No affiliation info available
Sjöberg PJ
No affiliation info available
Larhed M
No affiliation info available

MeSH

Boronic AcidsCatalysisEstersLigandsMicrowavesOrganometallic CompoundsPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19856344

Citation

Andaloussi, Mounir, et al. "Microwave-promoted palladium(II)-catalyzed C-P Bond Formation By Using Arylboronic Acids or Aryltrifluoroborates." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 15, no. 47, 2009, pp. 13069-74.
Andaloussi M, Lindh J, Sävmarker J, et al. Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates. Chemistry. 2009;15(47):13069-74.
Andaloussi, M., Lindh, J., Sävmarker, J., Sjöberg, P. J., & Larhed, M. (2009). Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates. Chemistry (Weinheim an Der Bergstrasse, Germany), 15(47), 13069-74. https://doi.org/10.1002/chem.200901473
Andaloussi M, et al. Microwave-promoted palladium(II)-catalyzed C-P Bond Formation By Using Arylboronic Acids or Aryltrifluoroborates. Chemistry. 2009 Dec 7;15(47):13069-74. PubMed PMID: 19856344.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates. AU - Andaloussi,Mounir, AU - Lindh,Jonas, AU - Sävmarker,Jonas, AU - Sjöberg,Per J R, AU - Larhed,Mats, PY - 2009/10/27/entrez PY - 2009/10/27/pubmed PY - 2010/1/30/medline SP - 13069 EP - 74 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 15 IS - 47 N2 - 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/19856344/Microwave_promoted_palladium_II__catalyzed_C_P_bond_formation_by_using_arylboronic_acids_or_aryltrifluoroborates_ L2 - https://doi.org/10.1002/chem.200901473 DB - PRIME DP - Unbound Medicine ER -