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Preparation of Arylphosphonates by Palladium(0)‐Catalyzed Cross‐Coupling in the Presence of Acetate Additives: Synthetic and Mechanistic Studies
Author(s) -
Kalek Marcin,
Jezowska Martina,
Stawinski Jacek
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900590
Subject(s) - chemistry , electrophile , trifluoromethanesulfonate , aryl , denticity , catalysis , palladium , combinatorial chemistry , phosphonate , coupling reaction , organic chemistry , alkyl , crystal structure
An efficient protocol for the synthesis of arylphosphonate diesters via a palladium‐catalyzed cross‐coupling of H‐phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross‐coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.