Easy access to phosphonothioates.
A new and particularly mild method for the formation of phosphorus-sulfur bonds has been achieved through base-catalyzed addition of thiocyanate to the corresponding H-phosphine oxide, phosphinate, or phosphonate. This reaction procedure offers many advantages: the use as starting material of a stable and not oxygen-sensitive phosphorus(v) species, particularly mild and nonaqueous reaction conditions and workup (a pivotal point for these sensitive phosphonothioates), and, through optimized access to thiocyanates, a wider scope of substrates. This method has been applied to achieve the synthesis of substrate analogues for the study of antibody-catalyzed hydrolysis of acetylcholinesterase inhibitor PhX (11).
Renard
Pierre-Yves
PY
Service des Molécules Marquées Bât. 547, 91191 Gif sur Yvette, France. pierre-yves.renard@cea.fr
Schwebel
Hervé
H
Vayron
Philippe
P
Josien
Ludovic
L
Valleix
Alain
A
Mioskowski
Charles
C
D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D063065:Organophosphonates / Q000138:chemical synthesis*; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis*; D013861:Thiocyanates / Q000737:chemistry
D002800:Cholinesterase Inhibitors; D004791:Enzyme Inhibitors; D063065:Organophosphonates; D009946:Organothiophosphorus Compounds; D013861:Thiocyanates