Microwave-promoted palladium(II)-catalyzed C-P bond formation by using arylboronic acids or aryltrifluoroborates.
2009 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 47, 13069-13074 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
Weinheim: Wiley-VCH Verlag GmbH , 2009. Vol. 15, no 47, 13069-13074 p.
Boronic acids, microwave chemistry, palladium, P arylation, trifluoroborates
Research subject Analytical Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-113919DOI: 10.1002/chem.200901473ISI: 000273697100021PubMedID: 19856344OAI: oai:DiVA.org:uu-113919DiVA: diva2:292144