Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters

Article abstract of DOI:10.1002/ejoc.201701411

An Fe(NO₃)₃·9H₂O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.

Full text of DOI:10.1002/ejoc.201701411

A Journal of
Accepted Article
Title: Iron Nitrate-Catalyzed Oxidative Esterification of Aldehydes and
Alcohols with NHPI: Efficient Synthesis of N-hydroxyimide Esters
Authors: Yuanyuan Xie, Xiaohe Xu, Jian Sun, Yuyan Lin, Pingping Li,
Jingya Cheng, Xiaoying Jiang, and Renren Bai
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201701411
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10.1002/ejoc.201701411
European Journal of Organic Chemistry
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Iron Nitrate-Catalyzed Oxidative Esterification of Aldehydes and
Alcohols with NHPI: Efficient Synthesis of N-hydroxyimide Esters
Xiaohe Xu,[a] Jian Sun,[a] Yuyan Lin,[a] Jingya Cheng,[a] Pingping Li,[a] Xiaoying Jiang,[a] Renren Bai[a]
and Yuanyuan Xie*[a],[b]
Abstract: An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative
coupling reaction between N-hydroxyphthalimide (NHPI) or N-
hydroxysuccinimide (NHSI) and aldehydes or alcohols in the air has
been described. This transformation provided an efficient approach
to prepare N-hydroxyimide ester derivatives with wide substrate
scope in moderate to excellent yields.
substrates are still required for the synthesis of N-hydroxyamide
esters.
Introduction
Ester groups are important functional groups in organic
chemistry and they can be found in natural products, medicinally
relevant molecules, synthetic materials, and polymers.[1]
Therefore, many methods have been developed for their
efficient constructions.[2] N-Hydroxyimide ester, an important
class of esters, is an active intermediate in preparing amides,
esters, O-substituted hydroxylamine and in the formation of Csp2
− Csp2 bonds by cross-coupling.[3] Although N-hydroxyimide
esters are frequently used intermediates, few approaches have
been developed for their preparation. Traditionally, N-
hydroxyamide esters were synthesized via direct coupling of
carboxylic acids with N-hydroxyimides in the presence of N,N'-
dicyclohexylcarbodiimide,[4] which suffers from several
drawbacks such as poor atom efficiency and difficult purification
process. The cross-dehydrogenative coupling approach is
attractive because it is atom-economic without the requirement
of the prefunctionalization of the substrates.[5] Recently, several
groups have reported N-hydroxyamide ester formation from
aldehydes via oxidative cross-dehydrogenative coupling either in
the presence of a metal catalyst or under metal-free conditions.[6]
These reported cross dehydrogenative coupling reactions
between N-hydroxyphthalimide and aldehydes were normally
applicable to aromatic aldehydes. The CDC reaction between
NHPI and alkyl aldehydes, enaldehydes or alcohols still remains
a major challenge. In 2013, Yu and co-workers developed a NaI
catalyzed cross-coupling reaction of alcohols with NHPI in the
presence of TBHP and KOH (Scheme 1).[7] Although the above-
mentioned elegant methods appear to be general and efficient,
they still suffer from some drawbacks, such as the stoichiometric
oxidants and heavy-metal catalysts. Hence, milder, more
environmentally benign synthetic methods with a wider scope of
Scheme 1. Various approaches for synthesis of N-hydroxyamide esters
Iron is the second most abundant metal in the earth.[8]
Compared with other metals, iron is relatively non-toxic,
inexpensive and environmentally friendly. Thus a variety of
organic transformations were carried out under iron-based
catalyst systems.[9] Recently, iron (III) nitrate nonahydrate
[Fe(NO3)3·9H2O] has been used as a nitration reagent, as well
as a widely used catalyst to catalyze the oxidation of benzyl
alcohols and oxidative coupling of NHPI with olefins.[10] Thermal
decomposition of Fe(NO3)3·9H2O is well-known to generate
nitrogen dioxide (NO2)[11] which is a radical species. In the
presence of NO2, NHPI can be oxidized to PINO, which may
initiate radical oxidative reactions.[12] Herein, we disclosed an
example of Fe(NO3)3·9H2O catalyzed intermolecular C–O cross-
coupling reaction of aldehydes or alcohols with NHPI.
Results and Discussion
In our initial study, propionaldehyde 1a and NHPI 2a were
chosen as the model substrates to investigate the cross-
dehydrogenative coupling reaction in CH3CN at room
temperature in the presence of Fe(NO3)3·9H2O under the air for
1 h, and the desired N-hydroxyamide ester 3aa was obtained in
13% yield (entry 1, Table 1). Intriguingly, elevated temperature
gave the desired product in a much better yield (entry 2). When
the temperature was increased up to 80 oC, the starting
materials NHPI was totally converted into the desired product
(entry 3). Other catalysts such as Cu(NO3)2·3H2O,
Mg(NO3)2·6H2O and AgNO3 were also tested, but they were less
active and gave 3aa in 72%, 59% and 50% yields, respectively
[a]
[b]
Collaborative Innovation Center of Yangtze River Delta Region
Green Pharmaceuticals
Zhejiang University of Technology
Hangzhou, PR China
College of Pharmaceutical Sciences
Zhejiang University of Technology
Hangzhou, PR China
E-mail: xyycz@zjut.edu.cn.
Supporting information for this article is given via a link at the end of
the document.((Please delete this text if not appropriate))
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Fe(NO3)3·9H2O was not added. [g] The reaction was performed under N2
atmosphere. n.d. = Not detected
(entries 4-6). The reaction did not afford the coupling product
when other iron salts such as FeCl3·6H2O and FeSO4·7H2O
-
were used (entries 7-8), which indicated the importance of NO3
With the optimized reaction conditions in hand, we then
investigated the scope of aldehyde substrates. As shown in
Table 2, a series of aldehydes were found to smoothly react with
NHPI, giving the corresponding products in good to excellent
yields. Aliphatic aldehydes like propionaldehyde, butyraldehyde
and pentanaldehyde delivered the related products 3aa, 3ab
and 3ac in 82%, 78% and 82% yields, respectively. Increasing in
linear chain showed little influence on the reaction efficiency,
gaving products 3ad-3af in 80-83%. Due to the steric effect, the
reaction efficiency of branched aliphatic aldehydes was
decreased. For example, when isobutyraldehyde was also used
as the substrate, the cross-dehydrogenative coupling product
3ag was obtained in only 69% yield (3ag vs 3aa, 3ab). Other
branched aliphatic aldehydes such as 3,3-dimethylbutanal,
pivalaldehyde and 2-methylpentanal displayed lower yields and
products 3ah, 3ai and 3aj were obtained in 77%, 72% and 76%,
respectively. The enaldehydes were identified to be suitable
substrates, providing esters 3ak-3am in 45-76% yields. This
work provides the first example of a direct transformation from
an alkyl enaldehydes and NHPI to the corresponding N-
hydroxyimide esters. The optimized conditions were also
compatible with benzyl aldehydes and 2-naphthaldehyde,
providing the desired products 3an-3aq in 93-96% yields.
Additionally, the heterocyclic aldehydes including thiophene-2-
carbaldehyde and furfural were survived. For instance, 1,3-
dioxoisoindolin-2-yl thiophene-2-carboxylate 3ar was produced
in 86% yield, and 1,3-dioxoisoindolin-2-yl furan-2-carboxylate
3as was formed in 33% yield.
in the reaction. However, the reaction did not occur in the
presence of NaNO2 (entry 9). As reported, NO2 can be
generated from NaNO2 under acidic conditions[13]. Considering
this transformations, 3aa was obtained in 55% when 3eq.
CH3COOH was added into the reaction mixture (entry 9).
Additionally, the effect of different solvents including EtOAc,
acetone, toluene and DMF were also investigated, and CH3CN
was showed to be the optimal solvent (entries 10-13).
Decreasing the Fe(NO3)3·9H2O dosage reduced the yield. When
the reaction time was prolonged to 4 h, the yield of 3aa was
increased to 76%, however, further prolonged the reaction time
and the yield of 3aa was unchanged (entry 14). Moreover, the
reaction did not take place in the absence of Fe(NO3)3·9H2O
(entry 15), when the reaction was performed under N2
atmosphere, the yield of 3aa was only 23% (entry 16).. The
results proved that both catalysts and oxidants (air) are crucial
for this transformation. Hence, the optimal conditions determined
were 1a (1.0 mmol) with 2a (0.5 mmol) in the presence of
Fe(NO3)3·9H2O (0.1 mmol) in CH3CN at 80 °C under air to afford
the desired product in 82% yield (entry 3).
Table 1. Optimization of the reaction conditions[a]
T. [oC]
r.t.
60
80
80
80
80
80
80
80
77
56
80
80
80
80
80
Slovent
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
EtOAc
Yield [%][b]
Table 2. Scope of the reaction of aldehydes with NHPI [a,b]
Entry
1
Catalyst
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
Cu(NO3)2·3H2O
Mg(NO3)2·6H2O
AgNO3
13
68
2
3
82
4
72
5
59
6
50
7
FeCl3·6H2O
n.d.
n.d.
trace [55][c]
46
8
FeSO4·7H2O
NaNO2
9
10
11
12
13
14[d]
15[f]
16[g]
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
Fe(NO3)3·9H2O
--
acetone
toluene
DMF
35
13
30
CH3CN
CH3CN
CH3CN
65 [76]e
n.d.
23
Fe(NO3)3·9H2O
[a] Unless otherwise mentioned, the reactions were performed with 1a (1.0
mmol), 2a (0.5 mmol), catalyst (20 mol%.), solvent (6.0 mL) under air for 1 h.
[b] Isolated yields based on 2a. [c] CH3COOH (3.0 equiv.) was added. [d] 10
mol% Fe(NO3)3·9H2O was used. [e] The reaction time was
4 h. [f]
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[a] All the reactions were performed with
1 (1 mmol), 2a (0.5 mmol),
hydroxyimide ester 3ao was not found under standard
conditions.
Fe(NO3)3·9H2O (0.1 mmol), CH3CN (6.0 mL) at 80 °C under air for 1 h. [b]
Isolated yields based on 2a.
Table 4. Scope of the reaction of alcohols with NHPI [a,b]
We then investigated the reaction of aldehydes with N-
hydroxysuccinimide (2b, NHSI) under optimized reaction
conditions. The results were displayed in Table 3. Aldehydes
with electron-withdrawing groups performed well, giving the
desired products 3ba-3bd in 50-81% yields. Other substituents
on the benzene ring of the aldehyde such as methoxyl, methyl,
ester group were all well-tolerated and the corresponding
products 3be-3bi were obtained in good to excellent isolated
yields. However, aliphatic aldehydes were turned out to be poor
substrates for this transformation.
Table 3. Scope of the reaction of aldehydes with NHSI [a,b]
[a] All the reactions were performed with
1 (1 mmol), 2b (0.5 mmol),
Fe(NO3)3·9H2O (0.1 mmol), CH3CN (6.0 mL) at 80 °C under air for 4 h unless
otherwise mentioned. [b] Isolated yields based on 2a. [c] The reaction was
performed for 24 h.
[a] All the reactions were performed with
1 (1 mmol), 2b (0.5 mmol),
Fe(NO3)3·9H2O (0.1 mmol), CH3CN (6.0 mL) at 80 °C under air for 1 h. [b]
Isolated yields based on 2b
Encouraged by the above mentioned discoveries, we further
investigated the possibility of using alcohols as the coupling
partner for NHPI since alcohols can be readily oxidized into
aldehydes by NHPI and Fe(NO3)3·9H2O. As shown in Table 4,
benzyl alcohols with various substituents, including electron-
withdrawing groups such as F, Cl, Br, CN, Ph and COOMe,
electron-donating groups such as OCH3 and CH3 could be
converted to the desired products in moderate to excellent yields.
Naphthalen-1-ylmethanol and 3-phenylprop-2-en-1-ol also
furnished the desired products 3aaa and 3ak in 59% and 20%
yields, respectively. Aliphatic alohols (4d-4f, 4b) were
investigated under the optimized conditions and resulted in the
corresponding products 3ad−3af, 3aab albeit in moderate yields
(58−68%)
Scheme 2. Control experiments
Based on the results of above experiments and according to
With the methods established, several control experiments
were carried out to probe the reaction mechanism (Scheme 2).
Under standard conditions, p-methoxybenzyl alcohol was
oxidized to p-methoxybenzaldehyde in 85% yield in 1 h (Scheme
2, a). When the reaction was performed under HNO3 condition,
the desired product 3ao was obtained in 46% yield (Scheme 2,
b).The esterification of 4-methoxybenzaldehyde (1o) with NHPI
(2a) was conducted in the presence of TEMPO under the
standard reaction conditions and only trace product 3ao was
obtained (Scheme 2, c). The model reaction was also
completely inhibited by another radical scavenger, 2,6-di-tert-
butyl-4-methylphenol (BHT) (Scheme 2, c). In order to verify
whether p-methoxybenzoic acid was formed in situ as an active
intermediate, p-methoxybenzoic acid was applied to the cross-
coupling reaction with NHPI (Scheme 2, d), and the N-
previous reports,[6,10-12]
a plausible reaction pathway was
illustrated in Scheme 3. Initially, ferric nitrate was hydrolyzed to
HNO3, and then thermal decomposition of HNO3 generates NO2.
In the gas phase of the reaction mixture, the presence of NO2
was confirmed by its characteristic reddish-brown color. In the
presence of NO2, NHPI could afford PINO radical, which induces
the homolysis of the C–H bond of the aldehyde to afford the acyl
radical B [14]. Finally, recombination of the acyl radical B and
PINO radical forms the N-hydroxyimide ester 3ao. On the other
hand, HNO2 decomposes into HNO3 and NO. In the presence of
O2, NO was oxidized to NO2 and NO2 was recycled.
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26.7, 22.0, 13.6 ppm. IR (KBr): v 3521, 3045, 2960, 2932, 1788, 1743,
1670, 1467, 1364, 1186, 1128, 1064, 878, 696, 518 cm-1. HRMS (ESI)
calcd for [M+Na]+ C13H13NNaO4, m/z 270.0737, found 270.0734.
1,3-dioxoisoindolin-2-yl hexanoate (3ad): Oil. 1H NMR (600 MHz,
CDCl3) δ = 7.91-7.90 (m, 2H), 7.81-7.80 (m, 2H), 2.68 (t, J = 7.2 Hz, 2 H),
1.84-1.79 (m, 2 H), 1.48-1.35 (m, 4 H), 0.95 (t, J = 7.2 Hz, 3 H) ppm. 13
C
NMR (125 MHz, CDCl3) δ = 169.7, 162.0, 134.7, 129.0, 123.9, 31.0, 24.4,
22.2, 13.8 ppm. IR (KBr): v 3059, 3031, 2957, 2931, 1789, 1744, 1467,
1363, 1186, 1311, 1066, 966, 878, 786, 697, 518 cm-1. HRMS (ESI)
calcd for [M+Na]+ C14H15NNaO4, m/z 284.0893, found 284.0888.
1,3-dioxoisoindolin-2-yl heptanoate (3ae): Oil. 1H NMR (600 MHz,
CDCl3) δ = 7.89-7.87 (m, 2 H), 7.80-7.78 (m, 2 H), 2.67 (t, J =7.2 Hz, 2 H),
1.81-1.76 (m, 2 H), 1.47-1.43 (m, 2 H), 1.35-1.33 (m, 4 H), 0.91 (t, J =7.2
Hz, 3 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 169.7, 162.0, 134.7, 128.9,
123.9, 31.3, 31.0, 28.5, 24.6, 22.4, 14.0 ppm. IR (KBr): v 3448, 3043,
3025, 2954, 2869, 1788, 1740, 1638, 1377, 1139, 1081, 877, 699, 521
cm-1. HRMS (ESI) calcd for [M+Na]+ C15H17NNaO4, m/z 298.1050, found
298.1041.
Scheme 3. Plausible mechanism
Conclusions
1,3-dioxoisoindolin-2-yl octanoate (3af): Oil. 1H NMR (600 MHz,
CDCl3) δ = 7.90-7.86 (m, 2 H), 7.80-7.77 (m, 2 H), 2.67-2.65 m, 2 H),
1.801-1.76 (m, 2 H), 1.43 (s, 2 H), 1.33-1.30 (m, 6 H), 0.90 (t, J =3.6 Hz,
3 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 169.7, 162.0, 134.7, 129.0,
123.9, 31.6, 31.0, 28.8, 24.7, 22.6, 14.1 ppm. IR (KBr): v 3065, 2958,
2928, 1789, 1745, 1467, 1364, 1185, 1072, 969, 878, 697, 518 cm-1.
HRMS (ESI) calcd for [M+Na]+ C16H19NNaO4, m/z 312.1206, found
312.1202.
In conclusion, we have described an efficient method for the
synthesis of N-hydroxyimide esters. The notable features of this
reaction are a broad substrate scope, environmentally benign
conditions. Using inexpensive, non-toxic catalyst and green
oxidant (air) as the oxidant makes this protocol to be an
attractive strategy in synthetic chemistry. This is also the first
report that simultaneous employed aldehydes and alcohols
(including alkyl aldehydes, enaldehydes and alcohols) as the
coupling partners for NHPI to afford the corresponding esters.
Further studies on the coupling of other compounds with N-
hydroxyimides are under investigation.
o
1,3-dioxoisoindolin-2-yl isobutyrate (3ag): white solid, m.p. 60-61 C.
1H NMR (600 MHz, CDCl3) δ = 7.89-7.88 (m, 2 H), 7.79-7.78 (m, 2 H),
2.99-2.94 (m, 1 H),1.38 (d, J =7.2 Hz, 6 H) ppm. 13C NMR (125 MHz,
CDCl3) δ = 173.1, 162.0, 134.7, 129.0, 123.9, 31.8, 18.8 ppm. IR (KBr): v
3447, 3084, 2985, 2925, 1782, 1740, 1466, 1187, 1053, 967, 876, 694,
520 cm-1. HRMS (ESI) calcd for [M+Na]+ C12H11NNaO4, m/z 256.0580,
found 256.0575.
Experimental Section
1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate (3ah): white solid, m.p.
General procedure for synthesis of 3aa: Propionaldehyde 1a (1.0
mmol), NHPI (0.5 mmol, 1.0 equiv.) and Fe(NO3)3·9H2O (0.1 mmol) were
dissolved in CH3CN (6.0 mL) and the mixture was stirred for 1 h at 80
ºC under air until NHPI was completely consumption. Then, the solvent
were removed under reduced pressure. The residue was washed with
saturated NaHCO3 and then extracted with EtOAc (2 × 20 mL). The
combined organic layers was dried over anhydrous Na2SO4 and
concentrated. The residue was purified by column chromatography on
silica gel (petroleum ether/EtOAc = 10:1) to afford the desired product
3aa as a white solid; yield: 90 mg (82%); m.p.88–90 oC.[6c] 1H NMR (600
MHz, CDCl3) δ = 7.90-7.88 (m, 2 H), 7.81-7.79 (m, 2 H), 2.46 (q, J = 7.8
Hz, 2 H), 1.32 (t, J = 7.2 Hz, 3 H) ppm. 13C NMR (125MHz, CDCl3) δ =
170.4, 162.0, 134.8, 128.9, 124.0, 24.5, 8.7 ppm. IR (KBr): v 3433, 3097,
2981, 2936, 1755, 1736, 1610, 1185, 1137, 1104, 1059, 1000, 876, 699,
520 cm-1. HRMS (ESI) calcd for [M+Na]+ C11H9NNaO4, m/z 242.0424,
found 242.0423.
o
92-93 C. 1H NMR (600 MHz, CDCl3) δ = 7.89-7.87 (m, 2 H), 7.79-7.78
(m, 2 H), 2.53 (s, 2 H), 1.17 (s, 9 H) ppm. 13C NMR (125 MHz, CDCl3) δ =
167.9, 162.1, 134.7, 129.0, 123.9, 44.6, 31.3, 29.5 ppm. IR (KBr): v 3428,
3072, 2963, 2926, 1782, 1736, 1468, 1370, 1286, 1182, 1090, 970, 878,
702, 519 cm-1. HRMS (ESI) calcd for [M+Na]+ C14H15NNaO4, m/z
284.0893, found 284.0892.
1
1,3-dioxoisoindolin-2-yl pivalate (3ai): Oil. H NMR (600 MHz, CDCl3)
δ = 7.89-7.87 (m, 2 H), 7.79-7.77 (m, 2 H), 1.44 (s, 9 H) ppm. 13C NMR
(125 MHz, CDCl3) δ = 174.4, 162.1, 134.7, 129.1, 123.9, 38.4, 27.0 ppm.
IR (KBr): v 3521, 3066, 3031, 2977, 2936, 1758, 1744, 1481, 1370, 1186,
1062, 1023, 965, 878, 696, 518 cm-1. HRMS (ESI) calcd for [M+Na]+
C13H13NNaO4, m/z 270.0737, found 270.0731.
1,3-dioxoisoindolin-2-yl 2-methylpentanoate (3aj): Oil. 1H NMR (600
MHz, CDCl3) δ = 7.89-7.87 (m, 2 H), 7.79-7.78 (m, 2 H), 2.88-2.82 (m, 1
H), 1.86-1.80 (m, 1 H), 1.61-1.57 (m, 1 H), 1.53-1.48 (m, 2 H), 1.35 (d, J
= 6.6 Hz, 3 H), 0.98 (t, J = 7.2 Hz, 3 H) ppm. 13C NMR (125 MHz, CDCl3)
δ = 172.8, 162.1, 134.7, 129.0, 123.9, 36.9, 35.8, 20.1, 16.9, 13.9 ppm.
IR (KBr): v 3431, 3097, 2958, 1768, 1743, 1635, 1377, 1141, 1102, 1045,
978, 877, 699, 518 cm-1. HRMS (ESI) calcd for [M+Na]+ C14H15NNaO4,
m/z 284.0893, found 284.0885.
1,3-dioxoisoindolin-2-yl butyrate (3ab): Oil.[6c] 1H NMR (600 MHz,
CDCl3) δ = 7.90-7.87 (m, 2 H), 7.81-7.78 (m, 2 H), 2.66 (t, J = 7.2 Hz, 2
H), 1.86-1.80 (m, 2 H), 1.08 (t, J = 7.2 Hz, 3 H) ppm. 13C NMR (125 MHz,
CDCl3) δ = 169.5, 162.0, 134.7, 128.9, 123.9, 32.8, 18.3, 13.4 ppm. IR
(KBr): v 3521, 3068, 2969, 2937, 1788, 1743, 1609, 1467, 1367, 1186,
1127, 1062, 969, 877, 787, 696, 518 cm-1. HRMS (ESI) calcd for [M+Na]+
C12H11NNaO4, m/z 256.0580, found 254.0591.
1,3-dioxoisoindolin-2-yl cinnamate (3ak): White solid, m.p. 143-145 °C.
[6c]
1H NMR (600 MHz, CDCl3) δ = 7.99 (d, J = 16.2 Hz, 1 H), 7.95-7.93
1,3-dioxoisoindolin-2-yl pentanoate (3ac): Oil. 1H NMR (600 MHz,
CDCl3) δ = 7.89-7.87 (m, 2 H), 7.79-7.78 (m, 2 H), 2.67 (t, J = 7.8 Hz, 2
H), 1.80-1.75 (m, 2 H), 1.51-1.45 (m, 2 H), 0.97 (t, J = 7.2 Hz, 3 H) ppm.
13C NMR (125 MHz, CDCl3) δ = 169.6, 162.0, 134.7, 129.0, 123.9, 30.7,
(m, 2 H), 7.84-7.82 (m, 2 H), 7.62 (d, J = 6.6 Hz, 2 H), 7.51-7.45 (m, 3 H),
6.69 (d, J = 16.2, 1 H) ppm. 13C NMR (125 MHz, CDCl3) δ 163.0, 162.1,
150.0, 134.8, 133.6, 131.6, 129.1, 129.0, 128.7, 124.0, 111.7 ppm. IR
(KBr): v 3438, 3036, 2926, 1744, 1630, 1384, 1139, 980, 927, 876, 620,
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10.1002/ejoc.201701411
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532 cm-1. HRMS (ESI) calcd for [M+Na]+ C17H11NNaO4, m/z 316.0580,
found 316.0582.
1 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 161.8, 154.5, 148.8, 139.9,
134.9, 128.9, 124.1, 122.2, 112.7 ppm. IR (KBr): v 3444, 3038, 2955,
2924, 1742, 1646, 1466, 1286, 1155, 1081, 1038, 875, 766, 698, 532,
518 cm-1. HRMS (ESI) calcd for [M+Na]+ C13H7NNaO5, m/z 280.0216,
found 280.0230.
1,3-dioxoisoindolin-2-yl-3-(4-methoxyphenyl)acrylate (3al): Brown
solid, m.p. 135-137 °C. 1H NMR (600 MHz, CDCl3) δ = 7.95-7.93 (m, 3 H),
7.83-7.81 (m, 2 H), 7.57 (d, J = 9.0 Hz, 2 H), 6.97 (d, J = 9.0 Hz, 2 H),
6.54 (d, J = 16.2 Hz, 1 H), 3.89 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3)
δ = 163.3, 162.5, 162.2, 149.7, 134.7, 130.6, 129.1, 126.4, 124.0, 114.6,
108.8, 55.5 ppm. IR (KBr): v 3448, 3046, 2929, 1778, 1744, 1635, 1363,
1145, 987, 947, 878, 626, 528 cm-1. HRMS (ESI) calcd for [M+Na]+
C18H13NNaO5, m/z 346.0690, found 346.0686.
1,3-dioxoisoindolin-2-yl benzoate (3at): White solid, m.p. 168-
170 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.22 (d, J = 7.8 Hz, 2 H), 7.96-
7.93 (m, 2 H), 7.85-7.83 (m, 2 H), 7.72 (t, J = 7.8 Hz, 1 H), 7.56 (t, J = 7.8
Hz, 2 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 162.8, 162.1, 134.9, 134.8,
130.7, 129.0, 128.9, 125.3, 124.0 ppm. IR (KBr): v 3438, 3040, 3018,
2917, 1773, 1734, 1640, 1237, 1140, 1021, 1007, 875, 697, 520 cm-1.
HRMS (ESI) calcd for [M+Na]+ C15H9NNaO4, m/z 290.0424, found
290.0424.
1,3-dioxoisoindolin-2-yl 3-methylbut-2-enoate (3am): White solid,
118-119 oC. 1H NMR (600 MHz, CDCl3) δ = 7.90-7.88 (m, 2 H), 7.79-7.78
(m, 2 H), 6.00 (t, J = 1.2 Hz, 1 H), 2.23 (d, J = 1.2 Hz, 3 H), 2.05 (d, J =
0.6 Hz, 3 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 165.5, 162.4, 161.8,
134.7, 129.1, 123.9, 110.0, 27.9, 21.1 ppm. IR (KBr): v 3521, 3034, 2960,
1786, 1743, 1614, 1467, 1367, 1186, 1135, 1065, 966, 878, 696, 518 cm-
1. HRMS (ESI) calcd for [M+Na]+ C13H11NNaO4, m/z 268.0580, found
268.0586.
1,3-dioxoisoindolin-2-yl 4-fluorobenzoate (3au): White solid, m.p. 189-
192 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.25-8.22 (m, 2 H), 7.94-7.93
(m, 2 H), 7.83-7.82 (m, 2 H), 7.24-7.21 (m, 2H) ppm. 13C NMR (125 MHz,
CDCl3) δ = 166.9 (1JC-F = 213.4 Hz), 162.0, 161.9, 134.9, 133.5 (3JC-F
=
8.1Hz), 129.0, 124.1, 121.6, (4JC-F = 2.5 Hz), 116.3 (2JC-F = 18.5 Hz) ppm.
IR (KBr): v 3436, 3053, 3024, 2920, 1773, 1736, 1602, 1239, 1189, 1033,
1009, 875, 700, 520 cm-1. HRMS (ESI) calcd for [M+Na]+ C15H8FNNaO4,
m/z 308.0330, found 308.0316.
1,3-dioxoisoindolin-2-yl 4-nitrobenzoate (3an): White solid, m.p. 198-
200 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 8.39 (s, 4 H), 7.97-7.94 (m, 2
H), 7.87-7.84 (m, 2 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 161.7, 161.3,
151.6, 135.1, 131.9, 130.8, 128.8, 124.2, 124.0 ppm. IR (KBr): v 3434,
3050, 2926, 1769, 1741, 1608, 1239, 1136, 1053, 1010, 875, 710, 520
cm-1. HRMS (ESI) calcd for [M+Na]+ C15H8N2NaO4, m/z 335.0275, found
335.0272.
1,3-dioxoisoindolin-2-yl-3-bromobenzoate (3av): White solid, m.p.
169-171 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.33 (t, J = 1.8 Hz, 1 H),
8.14-8.12 (m, 1 H), 7.95-7.92 (m, 2 H), 7.84-7.82 (m, 3 H), 7.43 (t, J = 8.4
Hz, 1 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 161.8, 161.7, 137.9, 134.9,
133.4, 130.5, 129.2, 128.9, 127.2, 124.1, 122.9 ppm. IR (KBr): v 3448,
3094, 3037, 2925, 1774, 1736, 1644, 1185, 1136, 1024, 874, 851, 728,
517 cm-1. HRMS (ESI) calcd for [M+Na]+ C15H8BrNNaO4, m/z 367.9529,
found 367.9508.
1,3-dioxoisoindolin-2-yl 4-methoxybenzoate (3ao): White solid, m.p.
160-162 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.17 (d, J = 8.4 Hz, 2 H),
7.94-7.93 (m, 2 H), 7.83-7.82 (m, 2 H), 7.02 (d, J = 8.4 Hz, 2 H), 3.92 (s,
3 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 164.9, 162.4, 162.2, 134.7,
132.9, 129.0, 124.0, 117.3, 114.2, 55.6 ppm. IR (KBr): v 3441, 3024,
2986, 1738, 1605, 1248, 1117, 922, 875, 710, 521 cm-1. HRMS (ESI)
calcd for [M+Na]+ C16H11NNaO5, m/z 320.0529, found 320.0529.
1,3-dioxoisoindolin-2-yl-2-chlorobenzoate (3aw): White solid, m.p.
165-167 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.22 (dd, J = 6.6, 1.2 Hz, 1
H), 7.96-7.94 (m, 2 H), 7.85-7.83 (m, 2 H), 7.61-7.57 (m, 2 H), 7.46-7.44
(m, 1 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 161.9, 161.2, 134.9, 134.6,
132.5, 131.7, 129.0, 126.9, 124.8, 124.1, 123.6 ppm. IR (KBr): v 3419,
3068, 2958, 1777, 1751, 1638, 1588, 1229, 1185, 1137, 1075, 996, 875,
694, 518 cm-1. HRMS (ESI) calcd for [M+Na]+ C15H8ClNNaO4, m/z
324.0034, found 324.0050.
1,3-dioxoisoindolin-2-yl 4-methylbenzoate (3ap): White solid, m.p.
164-165 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.10 (d, J = 7.8 Hz, 2 H),
7.95-7.93 (m, 2 H), 7.84-7.82 (m, 2 H), 7.35 (d, J = 8.4 Hz, 2 H), 2.48 (s,
3H) ppm. 13C NMR (125 MHz, CDCl3) δ = 162.8, 162.2, 146.1, 134.8,
130.7, 129.6, 129.1, 124.0, 122.4, 21.9. IR (KBr): v 3438, 3037, 2932,
1758, 1740, 1607, 1251, 1180, 1119, 1000, 875, 740, 701, 520 cm-1.
HRMS (ESI) calcd for [M+Na]+ C16H11NNaO4, m/z 304.0580, found
304.0585.
1,3-dioxoisoindolin-2-yl-4-cyanobenzoate (3ax): White solid, m.p.
218-220 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.33 (d, J = 8.4 Hz, 2 H),
7.98-7.96 (m, 2 H), 7.89-7.86 (m, 4 H) ppm. 13C NMR (125 MHz, CDCl3)
δ = 161.7, 161.5, 135.0, 132.6, 131.1, 129.2, 128.8, 124.2, 118.3, 117.4
ppm. IR (KBr): v 3438, 3043, 3020, 2928, 2235, 1776, 1744, 1602, 1229,
1169, 1053, 1000, 876, 696, 518 cm-1. HRMS (ESI) calcd for [M+Na]+
C16H8N2NaO4, m/z 315.0381, found 315.0388.
1,3-dioxoisoindolin-2-yl 2-naphthoate (3aq): Yellow solid, m.p. 195-
197 °C. 1H NMR (600 MHz, CDCl3) δ = 8.84 (s, 1 H), 8.16 (dd, J = 7.2,
1.2 Hz, 1 H), 8.02 (d, J = 8.4 Hz, 1 H), 7.99-7.94 (m, 4 H), 7.85-7.84 (m,
2H), 7.71-7.68 (m, 1 H), 7.64-7.61 (m, 1 H) ppm. 13C NMR (125 MHz,
CDCl3) δ = 163.0, 162.2, 136.3, 134.8, 133.0, 132.3, 129.7, 129.4, 129.1,
128.8, 128.0, 127.2, 125.2, 124.1, 122.4 ppm. IR (KBr): v 3445, 3046,
2923, 1770, 1735, 1628, 1177, 1126, 1044, 875, 757, 697, 519 cm-1.
HRMS (ESI) calcd for [M+Na]+ C19H11NNaO4, m/z 320.0566, found
320.0580.
1,3-dioxoisoindolin-2-yl biphenyl-4-carboxylate (3ay): White solid,
m.p. 208-210 °C. 1H NMR (600 MHz, CDCl3) δ = 8.29 (d, J = 8.4 Hz, 2 H),
7.98-7.95 (m, 2 H), 7.85-7.84 (m, 2 H), 7.79 (d, J = 8.4 Hz, 2 H), 7.69-
7.68 (m, 2 H), 7.53 (t, J = 7.2 Hz, 2 H), 7.47-7.45 (m, 2 H) ppm. 13C NMR
(125 MHz, CDCl3) δ = 162.8, 162.1, 147.7, 139.5, 134.8, 131.2, 129.1,
128.7, 127.5, 127.4, 124.1, 123.9 ppm. IR (KBr): v 3418, 3069, 3021,
2923, 1775, 1744, 1607, 1376, 1254, 1187, 1141, 1035, 1001, 876, 740,
694, 518 cm-1. HRMS (ESI) calcd for [M+Na]+ C21H13NNaO4, m/z
366.0737, found 366.0734.
1,3-dioxoisoindolin-2-yl thiophene-2-carboxylate (3ar): White solid,
m.p. 145-147 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 8.09 (d, J = 4.2, 1 H),
7.94-7.92 (m, 2 H), 7.83-7.81 (m, 2H), 8.00 (d, J = 4.8 Hz, 1 H), 7.23 (t, J
= 4.2 Hz, 1 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 162.0, 158.3, 136.7,
135.7, 134.9, 128.9, 128.4, 127.0, 124.1 ppm. IR (KBr): v 3442, 3043,
3023, 2926, 1777, 1740, 1639, 1410, 1247, 1187, 1134, 992, 724, 695,
518 cm-1. HRMS (ESI) calcd for [M+Na]+ C13H7NNaO4S, m/z 295.9988,
found 295.9995.
1,3-dioxoisoindolin-2-yl methyl terephthalate (3az): White solid, m.p.
180-182 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.29 (d, J = 8.4 Hz, 2 H),
8.21 (d, J = 8.4 Hz, 2 H), 7.97-7.94 (m, 2 H), 7.86-7.84 (m, 2 H), 4.00 (s,
3 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 165.8, 162.2, 161.9, 135.6,
134.9, 130.6, 129.9, 129.0, 128.9, 124.1, 52.7 ppm. IR (KBr): v 3422,
3094, 2961, 1772, 1739, 1637, 1280, 1237, 1138, 1103, 1043, 1010, 875,
696, 519 cm-1. HRMS (ESI) calcd for [M+Na]+ C17H11NNaO6, m/z
348.0468, found 348.0479.
1,3-dioxoisoindolin-2-yl furan-2-carboxylate (3as): White solid, m.p.
148-150 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 7.95-7.93 (m, 2 H), 7.85-
7.82 (m, 2 H), 7.78-7.77 (s, 1 H), 7.56 (d, J = 3.6 Hz, 1 H), 6.67-6.66 (m,
This article is protected by copyright. All rights reserved.

10.1002/ejoc.201701411
European Journal of Organic Chemistry
FULL PAPER
1,3-dioxoisoindolin-2-yl-1-naphthoate (3aaa): White solid, m.p. 181-
183 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.87 (d, J = 8.4 Hz, 1 H), 8.57
(dd, J = 6.6, 0.6 Hz, 1H), 8.19 (d, J = 7.8 Hz, 1H), 7.99-7.95 (m, 3 H),
7.85-7.84 (m, 2 H), 7.70-7.68 (m, 1 H), 7.63-7.60 (m, 2H) ppm. 13C NMR
(125 MHz, CDCl3) δ = 163.1, 162.3, 135.6, 134.8, 133.8, 131.9, 131.5,
129.1, 128.8, 128.7, 126.8, 125.4, 124.5, 124.1, 121.7 ppm. IR (KBr): v
3434, 3046, 2917, 1772, 1743, 1365, 1136, 1096, 978, 773, 695, 520 cm-
1. HRMS (ESI) calcd for [M+Na]+ C20H27NNaO4, m/z 340.0580, found
340.0569.
2,5-dioxopyrrolidin-1-yl-2-methoxybenzoate (3bg): White solid, m.p.
174-176 °C .[6c] 1H NMR (600 MHz, CDCl3) δ = 8.08 (dd, J = 6.0, 1.8 Hz, 1
H), 7.64-7.61 (m, 1 H), 7.06 (t, J = 7.8 Hz, 2 H), 3.95 (s, 3 H), 2.92 (s, 4 H)
ppm. 13C NMR (125 MHz, CDCl3) δ = 169.5, 160.7, 160.3, 136.0, 132.7,
120.3, 114.0, 112.2, 56.1, 25.7 ppm. IR (KBr): v 3434, 3074, 3029, 2983,
1768, 1740, 1470, 1231, 1100, 1076, 997, 898, 747, 700, 530 cm-1.
HRMS (ESI) calcd for [M+Na]+ C12H11NNaO5, m/z 272.0529, found
272.0539.
2,5-dioxopyrrolidin-1-yl 4-methylbenzoate (3bh): White solid, m.p.
173-175 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.04 (d, J = 8.4 Hz, 2 H),
7.33 (d, J = 8.4 Hz, 2 H), 2.91 (s, 4 H), 2.46 (s, 3 H) ppm. 13C NMR (125
MHz, CDCl3) δ = 169.4, 161.9, 146.1, 130.6, 129.6, 122.3, 25.7, 21.9
ppm. IR (KBr): v 3444, 3094, 3039, 2983, 1771, 1743, 1577, 1436, 1200,
1089, 1046, 1000, 878, 749, 696, 529 cm-1. HRMS (ESI) calcd for
[M+Na]+ C12H11NNaO4, m/z 256.0580, found 250.0590.
1,3-dioxoisoindolin-2-yl dodecanoate (3aab): Oil. 1H NMR (600 MHz,
CDCl3) δ = 7.89-7.88 (m, 2 H), 7.80-7.78 (m, 2 H), 2.66 (t, J =7.2 Hz, 2 H),
1.81-1.76 (m, 2 H), 1.47-1.42 (m, 2 H), 1.34-1.27 (m, 14 H), 0.88 (t, J
=7.2 Hz, 3H) ppm. 13C NMR (125 MHz, CDCl3) δ = 169.7, 162.0, 134.7,
129.0, 123.9, 31.9, 31.0, 29.58, 29.57, 29.4, 29.3, 29.1, 28.8, 24.7, 22.7,
14.1 ppm. IR (KBr): v 3427, 3091, 3062, 2954, 2920, 1789, 1744, 1375,
1185, 1143, 962, 880, 696, 521 cm-1. HRMS (ESI) calcd for [M+Na]+
C20H27NNaO4, m/z 368.1832, found 368.1815.
2,5-dioxopyrrolidin-1-yl methyl terephthalate (3bi): White solid, m.p.
173-174 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.22 (d, J = 7.2 Hz, 2 H),
8.19 (d, J = 7.2 Hz, 2 H), 3.99 (s, 3 H), 2.94 (s, 4 H) ppm. 13C NMR (125
MHz, CDCl3) δ 169.1, 165.8, 161.2, 135.6, 130.6, 129.9, 128.9, 52.7,
25.7 ppm. IR (KBr): v 3435, 3008, 2951, 1732, 1710, 1288, 1235, 1207,
1110, 1067, 1001, 845, 720, 529 cm-1. HRMS (ESI) calcd for [M+Na]+
C13H11NNaO6, m/z 300.0479, found 300.0490.
2,5-dioxopyrrolidin-1-yl 4-fluorobenzoate (3ba): White solid, m.p. 106-
108 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 8.20-8.17 (m, 2 H), 7.21 (t, J =
8.4 Hz, 2 H), 2.93 (s, 4 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 169.3,
166.9 (1JC-F = 213.5 Hz), 161.0, 133.4 (3JC-F = 8.1 Hz), 121.4 (4JC-F = 2.5
Hz), 116.3 (2JC-F = 18.5 Hz), 25.7 ppm. v 3430, 3074, 3023, 2964, 1778,
1730, 1598, 1400, 1085, 1056, 990, 846, 747, 530 cm-1. HRMS (ESI)
calcd for [M+Na]+ C11H8FNNaO4, m/z 260.0330, found 260.0320.
Acknowledgements
2,5-dioxopyrrolidin-1-yl 4-chlorobenzoate (3bb): White solid, m.p.
205-207 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 8.09 (d, J = 8.4 Hz, 2 H),
7.56 (d, J = 8.4 Hz, 2 H), 2.93 (s, 4 H) ppm. 13C NMR (125 MHz, CDCl3)
δ = 169.2, 161.2, 141.7, 131.9, 129.4, 123.6, 25.7 ppm. IR (KBr): v 3442,
3080, 3070, 2967, 1770, 1744, 1567, 1211, 1070, 1060, 991, 848, 730,
520 cm-1. HRMS (ESI) calcd for [M+Na]+ C11H8ClNNaO4, m/z 276.0034,
found 276.0018.
We are grateful to the National Natural Science Foundation of
China (No. 21576239) for financial support. We thank Dr. Qi
Shuai at Zhejiang University of Technology for helpful
discussions.
Keywords: Fe(NO3)3·9H2O • Cross-Dehydrogenative Coupling •
N-hydroxyimide Esters • Aldehydes • Alcohols
2,5-dioxopyrrolidin-1-yl 4-bromobenzoate (3bc): White solid, m.p.
206-208 °C.[6f] 1H NMR (600 MHz, CDCl3) δ = 8.01 (d, J = 8.4 Hz, 2 H),
7.69 (d, J = 8.4 Hz, 2 H), 2.93 (s, 4 H) ppm. 13C NMR (125 MHz, CDCl3)
δ = 169.1, 161.3, 132.4, 131.9, 130.5, 124.0, 25.7. IR (KBr): v 3432, 3084,
3069, 2974, 1773, 1727, 1588, 1406, 1211, 1080, 1066, 991, 848, 740,
531 cm-1. HRMS (ESI) calcd for [M+Na]+ C11H8BrNNaO4, m/z 319.9529,
found 319.9515.
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2005.
2,5-dioxopyrrolidin-1-yl 4-nitrobenzoate (3bd): White solid, m.p. 200-
203 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 8.40 (d, J = 9.0 Hz, 2 H), 8.35
(d, J = 9.0 Hz, 2 H), 2.97 (s, 4 H) ppm. 13C NMR (125 MHz, CDCl3) δ =
168.8, 160.3, 151.5, 131.8, 130.6, 124.0, 25.7 ppm. IR (KBr): v 3445,
3094, 3062, 2983, 1771, 1726, 1588, 1210, 1080, 1066, 991, 847, 740,
530 cm-1. HRMS (ESI) calcd for [M+Na]+ C11H8NNaO6, m/z 287.0380,
found 287.0392.
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2,5-dioxopyrrolidin-1-yl 4-methoxybenzoate (3be): White solid, m.p.
149-151 °C.[6b] 1H NMR (600 MHz, CDCl3) δ = 8.11 (d, J = 9.0 Hz, 2 H),
7.00 (d, J = 9.0 Hz, 2 H), 3.91 (s, 3 H), 2.91 (s, 4 H) ppm. 13C NMR (125
MHz, CDCl3) δ = 169.6, 164.9, 161.5, 132.9, 117.1, 114.2, 55.6, 25.7
ppm. IR (KBr): v 3445, 3081, 2974, 2932, 1766, 1736, 1602, 1514, 1428,
1217, 1183, 1074, 984, 848, 757, 595, 517 cm-1. HRMS (ESI) calcd for
[M+Na]+ C12H11NNaO5, m/z 272.0529, found 272.0532.
2,5-dioxopyrrolidin-1-yl 3-methoxybenzoate (3bf): White solid, m.p.
102-104 °C.[6c] 1H NMR (600 MHz, CDCl3) δ = 7.76 (dd, J = 7.2, 0.6 Hz, 1
H), 7.62 (t, J = 1.2 Hz, 1 H), 7.43 (t, J = 8.4 Hz, 1 H), 7.24-7.22 (m, 1 H),
3.87 (s, 3 H), 2.93 (s, 4 H) ppm. 13C NMR (125 MHz, CDCl3) δ = 169.4,
161.8, 159.7, 130.0, 126.2, 123.0, 121.7, 114.6, 55.6, 25.7 ppm. IR (KBr):
v 3445, 3094, 3049, 2963, 1770, 1744, 1570, 1426, 1201, 1089, 1076,
991, 858, 740, 696, 529 cm-1. HRMS (ESI) calcd for [M+Na]+
C12H11NNaO5, m/z 272.0529, found 272.0516.
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Entry for the Table of Contents (Please choose one layout)
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Xiaohe Xu, Jian Sun, Yuyan Lin, Jingya
Cheng, Pingping Li, Xiaoying Jiang ，
Renren Bai and Yuanyuan Xie*
Page No. – Page No.
Iron
Esterification of Aldehydes and
Alcohols with NHPI: Efficient
Synthesis of N-hydroxyimide Esters
Nitrate-Catalyzed
Oxidative
An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between
N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or
alcohols in air has been described.
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