Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate.
[reaction--see text] 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 triflates, the amphoteric character of the V=O unit in vanadyl species was proven to be responsible for the catalytic profile in this process.
Chen
C T
CT
Department of Chemistry, National Taiwan Normal University, Taipei, Taiwan, ROC. chefv043@scc.ntnu.edu.tw
Kuo
J H
JH
Li
C H
CH
Barhate
N B
NB
Hon
S W
SW
Li
T W
TW
Chao
S D
SD
Liu
C C
CC
Li
Y C
YC
Chang
I H
IH
Lin
J S
JS
Liu
C J
CJ
Chou
Y C
YC