D
M. Adib, R. Pashazadeh
Letter
Synlett
of 1a, the corresponding anhydride 2d was observed as the
major product (eq. IV). We also found that, in this oxidation
transformation, benzyl benzoate 8 could not be oxidized
with TBHP to afford the desired product 2a under the stan-
dard conditions (eq. V).8a
References and Notes
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OH
O
OOH
TBPB, PhCl
80 °C, 2.5 h
O
(I)
2
2a, 90%
+
+
Ph
1a
Ph
O
(2.2 equiv)
3, trace
.
O
OH
O
N
t-BuOOH (2.2 equiv)
+H C
(II)
+
2
2a, 0%
+
N
2
TBPB, PhCl
80 °C, 2.5 h
Ph
O
Ph
5, 93%
1a
4, (2.2 equiv)
CO2H
OH
t-BuOOH (2.2 equiv)
(III)
+
2a, 35% + 2ad, 0%
Ph
TBPB, PhCl
80 °C, 2.5 h
1a
6
7
CHO
OH
t-BuOOH (2.2 equiv)
(IV)
(V)
2a, trace 2ad, trace 2d, 76%
+ +
+
Ph
Ph
TBPB, PhCl
80 °C, 2.5 h
1a
O
t-BuOOH (2.2 equiv)
2a, 0%
O
Ph
TBPB, PhCl
80 °C, 2.5 h
8
Scheme 4 Control experiments
In conclusion, we have developed a CDC reaction for the
preparation of symmetrical carboxylic anhydrides. This re-
action was performed using the TBHP/n-Bu4PBr system to
oxidize and catalyze self-coupling of aryl methanols and
construct C–O and C=O bonds in the carboxylic anhydride
skeleton. TBHP acted as the oxidant and oxygen source to
construct the C–O and C=O bonds. The attractive features of
this protocol are the use of aryl methanols in place of alde-
hydes and carboxylic acid derivatives, simple operation,
moderate temperature, broad substrate scope, no require-
ment for transition-metal catalysts, and high yields of the
products. To the best of our knowledge, this is the first re-
port on the synthesis of carboxylic anhydrides using aryl
methanols as starting materials.
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Funding Information
This research was supported by the Research Council of University of
Tehran.
U)(nvieytrsi
of
Tehran
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Supporting Information
Supporting information for this article is available online at
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p
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ortiInfogrmoaitn
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–E