13330-42-2Relevant academic research and scientific papers
Nucleophilic acyl substitutions of anhydrides with protic nucleophiles catalyzed by amphoteric, oxomolybdenum species
Chen, Chien-Tien,Kuo, Jen-Huang,Pawar, Vijay D.,Munot, Yogesh S.,Weng, Shieu-Shien,Ku, Cheng-Hsiu,Liu, Cheng-Yuan
, p. 1188 - 1197 (2005)
(Chemical Equation Presented) Among six different group VIb oxometallic species examined, dioxomolybdenum dichloride and oxomolybdenum tetrachloride were the most efficient catalysts to facilitate nucleophilic acyl substitution (NAS) of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. In contrast to the well-recognized redox chemical behaviors associated with oxomolybdenum(VI) species, the catalytic NAS was unprecedented and tolerates virtually all kinds of functional groups. By using benzoic anhydride as a mediator for in situ generation of an incipient mixed anhydride-MoO2Cl2 adduct with a given functional alkanoic acid, one can achieve oleate, dipeptide, diphenylmethyl, N-Fmoc-α-amino, pyruvic, and tert-butylthio ester, N-tert-butylamide, and trityl methacrylate syntheses with appropriate protic nucleophiles. The amphoteric character of the Mo=O unit in oxomolybdenum chlorides was found to be responsible for the catalytic NAS profile as supported by a control NAS reaction of using an authentic adduct-MoOCl2(O2-CBu t)2 between pivalic anhydride and MoO2Cl 2 as the catalyst.
Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate
Chen, Chien-Tien,Chang, I-Hsin,Lin, Jin-Sheng,Liu, Chin-Jing,Chou, Y-Chen,Kuo, Jen-Huang,Li, Chun-Hsin,Barhate,Hon, Sang-Wen,Li, Tai-Wei,Chao, Shi-Deh,Liu, Chia-Cheng,Li, Ying-Chieh
, p. 3729 - 3732 (2007/10/03)
Figure presented Among four vanadyl species examined, vanadyl triflate was the most efficient catalyst to facilitate nucleophilic acyl substitution of anhydrides with a myriad array of alcohols, amines, and thiols in high yields and high chemoselectivity. By using mixed-anhydride technique, one can achieve oleate and peptide syntheses. In marked contrast to common metal Inflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
