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ChemComm
Table 4 Self-esterification of primary aliphatic alcohols over ABNO@
PMO-IL-Br under metal-free conditions
Notes and references
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Entry
R
t (h)
Conv.a (%)
1
2
3
4
5
6
7
8
PhCH2CH2
CH3(CH2)2
CH3(CH2)3
CH3(CH2)6
CH3(CH2)7
CH3(CH2)8
PhCH2CH2
PhCH2CH2
20
15
15
15
15
20
20
20
75
91
80
87
85
83
(95)b
94c
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a
Conditions. 1.5–2 mol% of catalyst in the presence of molecular
oxygen, 5 mol% HCl as an additive and 16 mol% TBN in 0.3 mL
toluene as a solvent. All products were detected using NMR spectro-
b
scopy. The progress of the reactions was monitored by GC. Using
Keto-ABNO (2 mol%), yields in parenthesis refer to the corresponding
aldehyde. Using SABNO (2 mol%), yield refer to the corresponding
c
aldehyde.
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see Scheme S1 in the ESI†). Attempts to synthesis self-esterification
products either using homogenous keto-ABNO or SABNO under
optimized conditions were unsuccessful (aldehydes are the sole
products). This result highlights the importance of near molecular
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imidazolium bromide network affords
a catalyst showing
enhanced catalytic activity in the metal-free aerobic oxidation of
numerous primary benzylic and secondary alcohols. Activity is
much higher than that of IL-free SABNO and PMO-IL function-
alized with TEMPO excellent catalysts, and even slightly higher
than homogenous keto-ABNO. The same ABNO@PMO-IL-Br solid
catalyst allows to perform the one-pot oxidative esterification of
non-activated aliphatic alcohols under mild reaction conditions.
The catalyst could be recycled in three consecutive reactions run in
the oxidation of benzyl alcohol with only a slight decrease in
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The authors acknowledge IASBS Research Councils, and
Iranian National Science Foundation (INSF) to grant the
research (No. 99022450), the Alexander von Humboldt Founda-
tion (B. K.), NanoQuebec and NSER Council of Canada (H. V.)
for support of this work.
Conflicts of interest
The authors have no conflicts of interest to declare.
Chem. Commun.
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