Sodium cyanide-promoted copper-catalysed aerobic oxidative synthesis of esters from aldehydes

Article abstract of DOI:10.1002/aoc.3766

A simple and efficient copper-catalysed procedure for oxidative esterification of aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a clean oxidant, is described. A variety of aromatic aldehydes and structurally different alcohols and phenols reacted efficiently, and the product esters were obtained in good to excellent yields under normal atmospheric and solvent-free conditions.

Full text of DOI:10.1002/aoc.3766

Received: 28 November 2016
DOI 10.1002/aoc.3766
Revised: 16 January 2017
Accepted: 21 January 2017
F U L L PA P E R
Sodium cyanide‐promoted copper‐catalysed aerobic oxidative
synthesis of esters from aldehydes
Najmeh Nowrouzi
| Mohammad Abbasi | Maryam Bagheri
Department of Chemistry, Faculty of
Sciences, Persian Gulf University, Bushehr
75169, Iran
A simple and efficient copper‐catalysed procedure for oxidative esterification of
aldehydes with alcohols and phenols mediated by sodium cyanide, using air as a
clean oxidant, is described. A variety of aromatic aldehydes and structurally differ-
ent alcohols and phenols reacted efficiently, and the product esters were obtained in
good to excellent yields under normal atmospheric and solvent‐free conditions.
Correspondence
Najmeh Nowrouzi, Department of
Chemistry, Faculty of Sciences, Persian Gulf
University, Bushehr 75169, Iran.
Email: nowrouzi@pgu.ac.ir
KEYWORDS
aerobic oxidation, alcohol, aldehyde, copper, ester, phenol
1 | INTRODUCTION
attention and has become an economically attractive alterna-
tive to traditional ester synthesis. Direct oxidative transforma-
Esterification reaction is one of the most important reactions
in organic synthesis that have been widely used in the chem-
ical and pharmaceutical industries.[1] Conventionally, ester
groups are synthesized by Fischer esterification which is a
reversible reaction requiring acid catalyst[2] or by treatment
of an alcohol with activated carboxylic acid derivatives in
the presence of a stoichiometric amount of bases.[1] An alter-
native protocol involves transition‐metal‐catalysed coupling
reactions. The first Pd‐catalysed three‐component esterifica-
tion of aryl halides, alcohols and carbon monoxide was
described by Heck and co‐workers in 1974.[3] Since that
pioneering report, several groups have studied these transfor-
mations using various Pd catalysts.[4] However, these proce-
dures suffer from one or more disadvantages, such as the
need for P ligands, elevated reaction temperatures and high
pressure of toxic and harmful CO gas. Moreover, Pd is an
expensive metal, and thus the Pd‐based reactions are less
attractive industrially. Some of these systems are also limited
to using aryl iodides. In 2015, Iranpoor et al. reported the first
NiCl2 catalytic system for the alkoxycarbonylation of aryl
iodides in the presence of Cr(CO)6 as the solid source of car-
bon monoxide under air.[5] Though efficient, replacement of
aryl halides as the coupling partners, which are generally
environmental pollutants, is important. Therefore, there is
still great interest in finding new methods and alternative
coupling partners for the preparation of esters. Recently, the
oxidative esterification of aldehydes has received growing
tion of an aldehyde moiety to an ester has been accomplished
in a variety of ways.[6] Among these, coupling of aldehydes
with alcohols in the presence of stoichiometric amounts of
oxidants,[7] N‐heterocyclic carbine activation[8] or transi-
tion‐metal‐mediated processes[9] are powerful strategies for
this purpose. As an inexpensive, easily obtainable and envi-
ronmental friendly catalyst, copper has been increasingly
employed in many oxidative reactions.[10]
By taking these points into consideration and in continu-
ation of our ongoing research interest in transition‐metal‐
catalysed cross‐coupling reactions,[11] we now introduce a
one‐pot procedure for Cu‐catalysed preparation of esters from
aldehydes and alcohols. To the best of our knowledge, a Cu‐
catalysed aerobic oxidative synthesis of esters through C─H
activation of aldehydes has not been reported previously.
2 | RESULTS AND DISCUSSION
Initial studies were performed using the reaction of p‐
methylbenzaldehyde (1.0 mmol) with 2‐phenylethanol (1.2
mmol) as the model reaction, employing CuI (20 mol%) as
the catalyst and tert‐butyl hydroperoxide (TBHP; 2.0 mmol)
as oxidant in dimethylformamide (DMF) at 100°C under nor-
mal atmospheric conditions (Table 1, entry 1). In this case,
the reaction did not proceed and no product was detected. It
was further observed that increasing the catalyst loading up
Appl Organometal Chem. 2017;e3766.
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https://doi.org/10.1002/aoc.3766

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NOWROUZI ET AL.
TABLE 1 Effect of reaction parameters on Cu‐catalysed synthesis of phenethyl 4‐methylbenzoatea,b
Entry
Catalyst (mol%)
Oxidant (mmol)
Solvent/additive
DMF/—
Temp. (°C)
Yield (%)c
1
2d
3
CuI (20)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
TBHP (2.0)
—
100
100
100
100
100
100
100
100
Reflux
Reflux
100
100
120
120
120
120
120
—
58
20
40
20
50
Trace
—
—
—
67
65
91
—
88
88
45
CuI (20)
DMF/NaCN
DMF/NaCN
DMF/NaCN
DMF/NaCN
DMF/NaCN
DMSO/NaCN
Toluene/NaCN
MeCN/NaCN
THF/NaCN
Cu(OAc)2 (20)
CuCl (20)
CuCl2 (20)
Cu(PPh3)3I (20)
CuI (20)
4
5
6
7
8
CuI (20)
9
CuI (20)
10
11e
12
13
14f
15
16
17g
CuI (20)
CuI (20)
—/NaCN
CuI (20)
—/NaCN
CuI (20)
—
—/NaCN
CuI (20)
—
—/NaCN
CuI (20)
—
—/NaCN (1.0 mml)
—/NaCN (0.5 mmol)
—/NaCN (0.3 mmol)
CuI (20)
—
CuI (20)
—
aAll reactions were carried out using 1.0 mmol of p‐methylbenzaldehyde and 1.2 mmol of 2‐phenylethanol.
bAll reactions were worked up after 24 h.
cIsolated yield.
d2.0 mmol of NaCN was added.
eReaction was carried out under solvent‐free conditions.
fReaction was carried out under nitrogen atmosphere.
gProduct was isolated after 48 h.
to 50 mol% did not have any effect on the progress of the
reaction. Similarly, increasing the amount of TBHP failed
to give any improvement. Inspired by the oxidation of cyano-
hydrins with manganese dioxide of Corey et al.,[7] a similar
reaction in the presence of NaCN was studied. Surprisingly,
we found that by addition of 2.0 mmol of sodium cyanide
to the reaction mixture, the reaction proceeded and afforded
the desired product after 24 h, albeit in moderate yield
(Table 1, entry 2). This promising result encouraged us to
improve the yield of the product. Performing the reaction in
the presence of other Cu‐based catalysts such as Cu(OAc)2,
CuCl, CuCl2 and Cu(PPh3)3I showed that the appropriate
choice of catalyst was CuI (Table 1, entries 3–6). Screening
of solvents under identical conditions revealed that DMF
was the most effective solvent in this coupling reaction,
whereas other solvents such as dimethylsulfoxide (DMSO),
toluene, MeCN and tetrahydrofuran (THF) were less effec-
tive (Table 1, entries 7–10). Next, we carried out the reaction
under solvent‐free conditions at 100°C. Interestingly, this
process provided the coupling product in better yield
(Table 1, entry 11). Disposal of organic solvents is a major
problem for the chemical industry. Furthermore, organic sol-
vents are expensive, toxic and flammable and are not recycla-
ble for the most part. Therefore, the subsequent reactions
were performed under solvent‐free conditions. Moreover, it
was interesting to find that when the TBHP as oxidant was
omitted from the reaction mixture, essentially identical
results were obtained (Table 1, entry 12). This result sug-
gested that atmospheric oxygen played a significant role in
the reaction. Decrease in the amount of the catalyst showed
a longer reaction time along with a lower yield and increase
in the catalyst loading beyond 20 mol% did not increase the
product yield appreciably. Control experiments indicated that
no reaction took place in the absence of the catalyst. The
reaction temperature played an important role in this transfor-
mation. A clear improvement of the yields was observed
when the reaction temperature was raised from 100 to 120°C
(Table 1, entry 13). Further increase in the reaction tempera-
ture did not affect the reaction appreciably. As expected,
when the reaction was carried out under nitrogen atmosphere,
no product was detected (Table 1, entry 14). On the other
hand, the reaction yield of the model reaction was decreased

NOWROUZI ET AL.
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TABLE 2 Cu‐catalysed oxidative esterification of aldehydes with various alcoholsa
Entry
Aldehyde
Alcohol
Product
Time (h)
Yield (%)b
1
23
91[12]
2
3
24
48
88[13]
75[13]
4
5
6
25
18
20
90[13]
92[13]
88[13]
7
8
9
28
33
48
82[14]
86[14]
77[5]
10
11
25
17
93[14]
89[15]
12
13
14
—
48
32
35
—
85[5]
80[16]
(Continues)

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NOWROUZI ET AL.
TABLE 2 (Continued)
Entry
Aldehyde
Alcohol
Product
Time (h)
Yield (%)b
15
32
83[16]
16
17
20
24
24
91[16]
—
—
—
18c
—
aReaction conditions: aldehyde (1.0 mmol), alcohol (1.2 mmol), NaCN (0.5 mmol), CuI (20 mol%) at 120°C.
bIsolated yield.
cBenzaldehyde was obtained under the optimum conditions.
from 91to 75%byblowingair intothereaction mixture ata rate
of about 5 ml min−1 using an air pump probably due to the
escape of organic reactants and product molecules at 120°C.
After that, the required amount of cyanide ion was optimized.
The results of Table 1 show that decreasing the amount of
NaCN from 2.0 to 0.5 eq. caused no effect on yield and
reaction time, but lower amounts of cyanide ion not only
extended the reaction time, but also greatly reduced the
reaction yield (Table 1, entries 15–17). Therefore, the
optimized reaction conditions are as follows: reacting 1.0 mmol
of p‐methylbenzaldehyde with 1.2 mmol of 2‐phenylethanol
and 0.5 mmol of NaCN in the presence of 20 mol% of CuI at
120°C.
With the optimized conditions in hand, a broad range of
substituted aldehydes were subjected to esterification with
2‐phenylethanol and 1‐octanol. As evident from Table 2, all
reactions with aromatic aldehydes proceeded smoothly in
good to excellent yields, and various functional groups, such
as methyl, methoxy, nitro and bromo groups, on the phenyl
ring of aldehydes were tolerated, whereas aliphatic aldehydes
did not react under the reaction conditions (Table 2, entry
12). Next, this protocol was extended to different alcohols.
As evident from Table 2, this reaction is not limited to pri-
mary alcohols. 2‐Octanol as a secondary alcohol also
afforded the desired products in good to excellent yields
when it was treated with structurally diverse aldehydes under
the reaction conditions. The reaction with primary alcohols
was slightly faster in comparison with the reactions when
bulkier secondary ones were used (Table 2, entries 7 and
13). Tertiary alcohol did not undergo esterification (Table 2,
entry 17), probably due to steric effects. It is also noteworthy
that the esterification of benzylic alcohols did not occur
under the reaction conditions. In this case, oxidation worked
as a competing reaction giving benzaldehydes.
Despite extensive efforts in the synthesis of simple esters,
less attention has been paid to the synthesis of aryl benzoate
derivatives. Aryl benzoates are important compounds with
wide‐ranging applications in organic and bioorganic chemis-
try.[17,18] The traditional syntheses of these compounds
involve the reaction of phenols with activated carboxylic acid
derivatives,[19] transesterification[20] and Baeyer–Villiger
oxidation reactions.[21] These reactions often require strong
acidic or basic conditions, which limit the substrate scope.
Recently, efforts have been devoted towards the oxidative
coupling between aldehydes and phenols.[22] However, in
many cases, a carbonyl group at the ortho position of the phe-
nolic function is essential for successful performance of the
reaction.[23]
Encouraged by the results obtained in the transformation
of aldehydes to esters with alcohols, we decided to investi-
gate the applicability of performing this protocol using
phenols as coupling partners. Therefore, we ran the reaction
of p‐methylbenzaldehyde with phenol under the optimal
conditions of ester formation with alcohols. In this case, the
reaction gave phenyl 4‐methylbenzoate in only 30% yield
after 48 h. To improve the reaction yield we screened other
solvents, oxidants and amount of phenol or copper salt in
the model reaction, but they were found to be less effective.

NOWROUZI ET AL.
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TABLE 3 Cu‐catalysed synthesis of benzoate esters via oxidative coupling of aldehydes with phenolsa
Entry
Aldehyde
Phenol
Product
Time (h)
Yield (%)b
1
23
91[5]
2
3
26
31
88[18]
84[18]
4
5
6
20
15
23
91[18]
92[18]
85[15]
7
8
25
15
92[24]
90[15]
9
48
48
48
75[15]
79[22]
81[22]
10
11
12
31
93[25]
(Continues)

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NOWROUZI ET AL.
TABLE 3 (Continued)
Entry
Aldehyde
Phenol
Product
Time (h)
Yield (%)b
13
25
84[22]
14
15
28
18
88[26]
90[26]
16
48
73[27]
17
18
48
23
79[5]
89[18]
aReaction conditions: aldehyde (1.0 mmol), phenol (1.2 mmol), NaCN (0.5 mmol), CuI (20 mol%), NaOH (1.2 mmol) at 120°C.
bIsolated yield.
To our delight, a clear improvement of the yield was observed
when 1.2 mmol of NaOH as base was added to the reaction
mixture. Having these results in hand, we were able to extend
the applicability of this protocol for the oxidative coupling of
substituted benzaldehydes with a range of phenols (Table 3).
Various benzaldehydes, including those containing electron‐
withdrawing and electron‐releasing groups, were readily
converted to the corresponding products in excellent yields.
Substituted phenols were also tested in the reaction with
aldehydes and the desired aryl esters were efficiently formed.
Generally, the reaction of electron‐rich phenols with alde-
hydes was found to be completed in shorter time than that of
electron‐deficient phenols (e.g. Table 3, entries 6 and 8 ver-
sus 9 and 12). On the other hand, the electron‐rich aldehydes
provided the desired products slower than electron‐poor ones
(Table 3, entries 1–5). The steric hindrance of phenols had a
sharp effect on the reaction. For example, 93% esterified
product was isolated within 31 h when 4‐nitrophenol was
used as the substrate in reaction with 4‐nitrobenzaldehyde
(Table 3, entry 12), while 2‐nitrophenyl‐4‐nitrobenzoate
was obtained in 73% yield after 48 h, in the case of 2‐nitro-
phenol (Table 3, entry 16).
Based on our experimental data and the literature, we
propose the following catalytic cycle for aerobic oxidation
of aldehydes with alcohols (Scheme 1). Since the catalytic
activity is not evident in the absence of cyanide ion, in the first
step, formation of cyanohydrin from the reaction of aldehydes
with sodium cyanide is expected. Subsequently, the formed
SCHEME 1 Proposed mechanism for aerobic oxidative synthesis of
esters

NOWROUZI ET AL.
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cyanohydrin is converted to an acyl cyanide intermediate in
the presence of Cu(II) species (generated in situ from aerobic
oxidation of Cu(I)). Finally, the nucleophilic addition of
alcohols on acyl cyanide intermediate affords the desired ester
and Cu(I) catalyst which can be re‐oxidized to Cu(II) by air.
were identified by their spectral data and comparison
with authentic samples.
4.3 | Typical Reaction of p‐Methylbenzaldehyde,
2‐Phenylethanol and NaCN in Presence of CuI
under Nitrogen Atmosphere
3 | CONCLUSIONS
A 50 ml two‐neck flask containing p‐methylbenzaldehyde
(1.0 mmol), 2‐phenylethanol (1.2 mmol), NaCN (0.5 mmol,
0.024 g) and CuI (20 mol%, 0.038 g) was fitted with a gas
inlet and a magnetic stir bar. A condenser equipped with a
balloon was attached, and the apparatus was evacuated before
filling with nitrogen. The mixture was stirred at 120°C for 24
h. After that, the mixture was cooled to room temperature and
extracted with ethyl acetate (3 × 3 ml). The extract was
analysed by TLC. No product was detected. However, the
organic mixture was subjected to column chromatography
over silica gel using 10:1 n‐hexane–ethyl acetate as
eluent to separate unreacted p‐methylbenzaldehyde and 2‐
phenylethanol, separated in, respectively, 85 and 94% yields.
We described a cu‐catalysed aerobic oxidative esterification
of aldehydes with alcohols and phenols under solvent‐free
conditions mediated by sodium cyanide. oxygen as a clean
oxidant was used in this simple one‐pot process, producing
esters in good to excellent yields. although nacn is toxic,
the presented procedure obviates the employment of stoichio-
metric amounts of oxidants or environmental contaminant
aryl halides. the system was selective for primary and sec-
ondary alcohols and was not suitable for the use of tertiary
alcohols and benzylic alcohols as nucleophiles.
4 | EXPERIMENTAL
ACKNOWLEDGEMENT
4.1 | General Procedure for Cu‐Catalysed
Esterification of Aldehydes with Alcohols
We thank the Persian Gulf University Research Council for
support of this study.
To a 25 ml round‐bottom flask equipped with a magnetic stir-
rer bar and a condenser, an aldehyde (1.0 mmol), an alcohol
(1.2 mmol), NaCN (0.5 mmol, 0.024 g) and CuI (20 mol%,
0.038 g) were added. The reaction mixture was heated in an
oil bath at 120°C. The progress of the reaction was monitored
by TLC. After the completion of the reaction, the mixture was
cooled to room temperature and the product was extracted
with ethyl acetate (3 × 3 ml). The solvent was then evaporated
to leave the crude product, which was purified by column
chromatography over silica gel using n‐hexane as eluent to
afford the highly pure product. The products were identified
by their spectral data and comparison with authentic samples.
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How to cite this article: Nowrouzi N, Abbasi M,
Bagheri M. Sodium cyanide‐promoted copper‐
catalysed aerobic oxidative synthesis of esters from
aldehydes. Appl Organometal Chem. 2017;e3766.
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