Catalytic Staudinger-Vilarrasa reaction for the direct ligation of carboxylic acids and azides.
2,2'-Dipyridyl diselenide (PySeSePy) is the catalyst or activator of choice for the direct reaction of carboxylic acids with azides and trimethylphosphine at room temperature. The mechanism of the process, which is not an aza-Wittig reaction, has been elucidated.
Burés
Jordi
J
Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, 08028 Barcelona, Catalonia, Spain.
Martín
Manuel
M
Urpí
Fèlix
F
Vilarrasa
Jaume
J
D015082:2,2'-Dipyridyl / Q000031:analogs & derivatives* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D016566:Organoselenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D001386:Azides; D002264:Carboxylic Acids; D016566:Organoselenium Compounds; D015082:2,2'-Dipyridyl; C012945:2,2'-dipyridyl diselenide