Copper(II) acetate-mediated cross-coupling of phenylboronic acids with aryloximes: Synthesis of O-aryloximes

Article abstract of DOI:10.1080/00397910802590910

A novel method for the synthesis of O-aryloxime is described. It consisted of the coupling reaction between phenylboronic acids and aryloximes in the presence of catalytic quantities of copper(II) acetate. This reaction takes place in the presence of pyri

Full text of DOI:10.1080/00397910802590910

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Copper(II) Acetate–Mediated
Cross-Coupling of
Phenylboronic Acids with
Aryloximes: Synthesis of O-
Aryloximes
Xing-Hua Feng a , Guo-Zhen Zhang a , Cheng-Qun
Chen a , Ming-Yu Yang a , Xiao-Yun Xu a & Guo-Sheng
Huang a
a State Key Laboratory of Applied Organic Chemistry,
Lanzhou University, Lanzhou, China
Published online: 15 Apr 2009.
To cite this article: Xing-Hua Feng , Guo-Zhen Zhang , Cheng-Qun Chen , Ming-Yu
Yang , Xiao-Yun Xu & Guo-Sheng Huang (2009) Copper(II) Acetate–Mediated Cross-
Coupling of Phenylboronic Acids with Aryloximes: Synthesis of O-Aryloximes, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 39:10, 1768-1780
To link to this article: http://dx.doi.org/10.1080/00397910802590910
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Synthetic Communications1, 39: 1768–1780, 2009
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910802590910
Copper(II) Acetate–Mediated Cross-Coupling
of Phenylboronic Acids with Aryloximes:
Synthesis of O-Aryloximes
Xing-Hua Feng, Guo-Zhen Zhang, Cheng-Qun Chen,
Ming-Yu Yang, Xiao-Yun Xu, and Guo-Sheng Huang
State Key Laboratory of Applied Organic Chemistry, Lanzhou University,
Lanzhou, China
Abstract: A novel method for the synthesis of O-aryloxime is described. It con-
sisted of the coupling reaction between phenylboronic acids and aryloximes in
the presence of catalytic quantities of copper(II) acetate. This reaction takes
place in the presence of pyridine under a mild condition (DCE, Rt, 24–36 h)
with moderate yield. It represents a good alternative to known methods for
O-aryloxime synthesis.
Keywords: Aryloxime, copper(II) acetate, O-arylation, O-aryloxime, phenylboron-
ic acids
During the past few years, much attention has been devoted to the
synthesis of O-aryloximes because of their potential applications in med-
icinal and bioorganic chemistry.[1] Known methods for the synthesis of
O-aryloxime ethers include the reaction of the sodium salt of oxime with
fluorobenzene derivatives,[2] aldehydes=ketones with o-phenylhydroxyla-
mine,[3] or oximes with aryl nitrates=diazonium salts.[4] However, these
procedures lack generality, and the reaction often reacted at harsh condi-
tions. Recently, De and coworkers investigated a method for synthesis of
Received July 4, 2008.
Address correspondence to Guo-Sheng Huang, State Key Laboratory of
Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, China.
E-mail: hgs2368@163.com
1768

Coupling of Phenylboronic Acids with Aryloximes
1769
Scheme 1. Cross-coupling of aryloximes with phenylboronic acids.
O-aryloximes using CuI-mediated cross-coupling of aryl halides with oxi-
mes.[5] However, in most of the cases, only iodobenzene gave a good yield.
Previous work by Chan,[6] Cundy,[7] and Evans[8] and their coworkers
has revealed the efficacy of copper(II) acetate in the mediation of the
cross-coupling of aryl boronic acids and phenols or amines to give biaryl
ethers[9] and aryl alkylamines[10] or the like.[11,12] Inspired by these works,
we developed a similar procedure for the synthesis of O-aryloximes,
which consisted of the coupling reaction between commercially available
arylboronic acids derivatives and aryloximes. Herein we report the
success of this approach as shown in Scheme 1.
Our initial study began with the reaction of 2 equiv. of phenylboronic
acids, 1 equiv. of acetophenone oxime (0.25 mmol), and 3 equiv. of Et3N
with 1 equiv. of Cu(OAc)2 as the catalyst in CH2Cl2 at room temperature
under atmosphere for 24–48 h. The desired product 3a was isolated in a
35% yield (Table 1, entry 1). The effect of the different base on the reac-
tion was examined. It could be seen from Table 1 that pyridine gave the
best result, superior to dimethylaminopyridine (DMAP), Cs2CO3, and
Et3N (entries 1–4). This revealed that pyridine was by far the best base
for the reaction.[11a]
According to our investigation, the optimal ratio of 1a and 2a is 1=2.5
(entry 8, Table 1), which gives the highest yield. Reducing the ratio of 2a
and 1a gives less yield (table 1, entry 7), but greater quantities of phenyl-
boronic acid has little further benefit on the reaction (entry 9, Table 1).
Further optimization of the reaction conditions revealed that 1,2-
dichloroethane (DCE) was more effective solvent than dichloromethane
(DCM). Furthermore, we found that a catalytic amount (20% mmol)
of Cu(OAc)2 is adequate for the reaction, and increasing this amount
does not improve the reaction yield.
Under the optimized reaction conditions previously, the breadth
and scope for the reaction were investigated. As shown in Table 2,
compounds 1a, 1b, as well as 4-methoxybenzaldehyde oxime (1c) ben-
zo[d][1,3]dioxole-5-carbaldehyde oxime (1d), produced the corresponding
oxime ethers in good yields when react with phenylboronic acid (Table 2,
entries 1, 6, 9, 11, 12). Compared to aryloxime, acetophenone oxime (1a)
and 1-(4-methoxyphenyl)ethanone oxime (1b) gave good yields. When

1770
X.-H. Feng et al.
Table 1. Optimization of the base for the cross-coupling of acetophenone oxime
1a with phenylboronic acid 2a
Entrya
Catalyst
Base
Et3N
Base equiv.
1a=2a
Yield (%)b
1
2
3
4
5
6
7
8
9
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
Cu(OAc)2
3
3
3
3
1
3
5
3
3
1=2
1=2
1=2
1=2
1=2
1=2
1=2
1=2.5
1=3
35
Trace
30
Trace
43
63
62
76
75
K2CO3
Cs2CO3
DMAP
Pyridine
Pyridine
Pyridine
Pyridine
Pyridine
a
˚
Reaction conditions: 0.25 mmol acetophenone oxime, 150 mg of 4-A molecu-
lar sieves (freshly activated), 1 equiv. Cu(OAc)2, and the base in CH2Cl2, at room
temperature for 24–36 h under an air atmosphere.
bIsolated yield of 3a.
phenylboronic acid or p-tolylboronic acids are used, the corresponding
coupling products are obtained in good yields (Table 2, entries 1, 4, 7).
However, when p-fluorophenylboronic acid is employed, the yield is
decreased notably (Table 2, entries 4, 10).[10e] In general, the reaction is
affected by steric hindrance of the reaction center (Table 2, entry 5). Ary-
loximes with electron-withdrawing groups or electron-donating groups
undergo the reaction smoothly. In all cases, the boronic acid was con-
sumed during the reaction, and a small quantity of diphenyl ether was
observed as an unwanted side product.[13] To investigate the reasons
for the formation of diphenyl ether, a control experiment was carried
out under the same conditions with no aryloximes. Interestingly, no
diphenyl ether was observed under this condition. It seems that the ary-
loximes played a key role in the formation of diphenyl ethers.
In summary, we have developed a novel and mild methodology for
the synthesis of O-aryloxime. The reaction of phenylboronic acids with
aryloxime in the presence of catalytic quantities of copper(II) acetate
affords moderate to good yields of O-aryloximes. It represents a good
alternative to known methods for O-aryloxime synthesis.

1771

1772

1773

1774

Coupling of Phenylboronic Acids with Aryloximes
REPRESENTATIVE PRODUCTS
1775
Acetophenone O-Phenyl Oxime (3a): General Procedure for the
Preparation of O-Aryloxime
A mixture of acetophenone oxime (34 mg, 0.25mmol), phenylboronic acid
˚
(76mg, 0.625 mmol), Cu(OAc)2 (9 mg, 0.05mmol), freshly actived 4-A
molecular sieves (MS) (150 mg), and anhydrous pyridine (0.75 mmol) was
run in DCE (2 mL) under atmosphere at room temperature. During this
time, the color changed from blue to dark green. When the reaction was
considered complete, the mixture was extracted with EtOAc. The combined
organic extracts were washed with water and saturated brine. The organic
layers were dried over MgSO4 and filtered. Solvents were evaporated under
reduced pressure. The residue was purified by chromatography on silica gel
to afford acetophenone O-phenyl oxime (3a) as colorless oil (42 mg, 81%).
IR (KBr): 1592, 1489, 1216, 921, 755, 691 cmꢀ1. 1H NMR (300 MHz,
CDCl3) d: 7.79–7.76 (m, 2H), 7.42–7.27 (m, 7H), 7.03 (t, 2H), 2.45 (s, 3H,
-CH3); 13C NMR (75 MHz, CDCl3) d: 159.5, 157.7, 135.9, 129.7, 129.2,
128.5, 126.4, 122.1, 114.7, 13.3; MS (EI): m=z ¼ 211 [Mþ], 169, 118
(fission of the N-O bond), 77, 51. Anal. calcd. for C14H13NO: C, 79.59;
H, 6.20. Found: C, 79.36; H, 6.18.
Acetophenone O-3-Nitrophenyl Oxime (3b)
Yellow oil. IR (KBr): 1528, 1349, 1224 cmꢀ1 1H NMR (300 MHz,
.
CDCl3) d: 8.19–8.17 (1H), 7.91–7.88 (1H), 7.80–7.77 (m, 2H), 7.60–
7.578 (ddd, 1H), 7.50–7.45 (m, 4H), 2.49 (s, 3H, -CH3). 13C NMR
(75 MHz, CDCl3) d: 159.9, 159.4, 149.0, 135.1, 130.2, 129.7, 128.6,
126.6, 120.9, 116.8, 109.9, 13.6. MS (EI): m=z ¼ 256 [Mþ], 118 (fission
of the N-O bond), 221, 77. Anal. calcd. for C14H12N2O3: C, 65.62; H,
4.72; N, 10.93. Found: C, 65.56; H, 4.86; N, 10.69.
Acetophenone O-4-Tolyl Oxime (3c)
Colorless oil. IR (KBr): 2924, 1503, 1216, 911, 734 cmꢀ1 1H NMR
.
(300 MHz, CDCl3) d: 7.79–7.73 (m, 3H), 7.40–7.38 (m, 3H), 7.21–7.10
(m, 4H) 2.401 (s, 3H, -CH3), 2.31 (s, 3H, -CH3). 13C NMR (75 MHz,
CDCl3) d: 157.5, 157.3, 136.0, 131.4, 129.6, 129.5, 128.4, 126.4, 114.6,
20.6, 13.3. MS (EI): m=z ¼ 225 [Mþ], 118 (fission of the N-O bond), 77,
51. Anal. calcd. for C15H15NO: C, 79.97; H, 6.71; N, 6.22. Found: C,
79.99; H, 6.54; N, 6.52.

1776
X.-H. Feng et al.
Acetophenone O-4-Chlorophenyl Oxime (3d)
White solid. Mp 53–56ꢁC. IR (KBr): 1483, 1220, 918, 823, 759, 689 cmꢀ1
.
1H NMR (300 MHz, CDCl3) d: 7.78–7.74 (m, 2H), 7.44–7.41 (m, 3H),
7.30–7.21 (m, 4H), 2.44 (s, 3H, -CH3). 13C NMR (75 MHz, CDCl3) d:
158.2, 158.1, 135.6, 129.8, 129.1, 128.5, 126.8, 126.4, 115.9, 13.4. MS
(EI): m=z ¼ 245 [Mþ], 118 (fission of the N-O bond), 77, 51. Anal. calcd.
for C14H12ClNO: C, 68.44; H, 4.92; Cl, 14.43; N, 5.70, Found: C, 68.76;
H, 4.53; Cl, 14.58; N, 5.98.
1-(4-Methoxyphenyl)ethanone O-Phenyl Oxime (3f)
Colorless solid. Mp 32–34ꢁC. IR (KBr): 1592, 1487, 1252, 1217, 916,
753 cmꢀ1 1H NMR (300 MHz, CDCl3) d: 7.73 (2H), 7.35–7.24 (m,
.
4H), 7.01 (1H), 6.92 (2H), 3.83 (s, 3H), 2.41 (s, 3H). 13C NMR
(75 MHz, CDCl3) d: 160.9, 159.6, 157.2, 129.2, 128.4, 127.8, 121.9,
114.7, 113.8, 55.3, 13.1. MS (EI): m=z ¼ 241[Mþ], 148 (fission of the N-
O bond), 77. Anal. calcd. for C15H15NO2: C, 74.67; H, 6.27; N, 5.81.
Found: C, 74.28; 6.05; N, 5.46.
1-(4-Methoxyphenyl)ethanone O-p-Tolyl Oxime (3g)
1
IR (KBr): 1593, 1488, 1253, 1217, 916, 752 cmꢀ1. H NMR (300 MHz,
CDCl3) d: 7.74–7.71 (m, 2H), 7.26–7.10 (m, 4H), 6.94–6.91 (m, 2H),
3.84 (s, 3H, -OCH3), 2.40 (s, 3H), 2.31 (s, 3H). 13C NMR (75 MHz,
CDCl3) d: 160.9, 159.6, 157.2, 129.2, 128.4, 127.8, 121.9, 114.9, 113.8,
55.3, 20.6, 13.2. MS (EI): m=z ¼ 255 [Mþ], 148 (fission of the N-O bond),
77. Anal. calcd. for C16H17NO2: C, 75.27; H, 6.71; N, 5.49. Found: C,
75.05, H, 6.24; N, 5.67.
4-Methoxybenzaldehyde O-Phenyl Oxime (3h)
Colorless oil. IR (KBr): 2933, 1604, 1593, 1512, 1487, 1255, 1219, 931,
1
752, 691 cmꢀ1. H NMR (300 MHz, CDCl3) d: 8.36 (s, 1H), 7.68–7.65
(m, 2H), 7.34–7.25 (m, 4H), 7.09–7.02 (m, 1H), 6.96–6.93 (m, 2H). 13C
NMR (75 MHz, CDCl3) d: 161.4, 159.4, 151.1, 129.2, 129.1, 123.9,
122.0, 114.3, 114.2, 55.3. MS (EI): m=z ¼ 227 [Mþ], 169, 134 (fission of
the N-O bond), 77, 51. Anal. calcd. for C14H13NO2: C, 73.99; H, 5.77;
N, 6.16, Found: C, 73.64; H, 5.89; N, 6.27.

Coupling of Phenylboronic Acids with Aryloximes
1777
4-Methoxybenzaldehyde O-4-Chlorophenyl Oxime (3i)
ꢀ1
ꢁ
Waxy solid. Mp 46–48 C. IR (KBr): 1605, 1483, 1258, 1029, 827 cm
.
1H NMR (300 MHz, CDCl3) d: 8.34 (s, 1H), 7.66–7.64 (d, J ¼ 8.7 Hz,
2H), 7.269–7.263 (d, J ¼ 8.7 Hz, 2H), 7.19–7.17 (d, J ¼ 9.6 Hz, 2H),
6.96–6.93 (d, J ¼ 9.0 Hz, 2H), 3.85 (s, 3H, OCH3). 13C NMR (75 MHz,
CDCl3) d: 161.6, 158.0, 151.6, 129.2, 129.1, 126.7, 123.6, 115.6, 114.3,
55.3. MS (EI): m=z ¼ 261[Mþ], 134 (fission of the N-O bond), 77. Anal.
calcd. for C14H12ClNO2: C, 64.25; H, 4.62; Cl, 13.55; N, 5.35. Found:
C, 64.68; H, 4.25; Cl, 13.67; N, 5.67.
Benzo[d][1,3]dioxole-5-carbaldehyde O-Phenyl Oxime (3j)
Colorless oil. IR (neat): 2918, 1592, 1487, 1255, 1217, 1039, 936, 753 cmꢀ1
.
1H NMR (300 MHz, CDCl3) d: 8.32 (s, 1H), 7.37–7.32 (m, 3H), 7.27–7.24
(m, 2H), 7.10–7.02 (m, 2H), 6.86–6.83 (m, 1H), 6.03 (s, 2H). 13C NMR
(75 MHz, CDCl3) d: 159.3, 151.1, 149.8, 148.2, 129.2, 125.6, 123.8,
122.1, 114.3, 108.3, 105.9, 101.5. MS (EI): m=z ¼ 241 [Mþ], 148 (fission
of the N-O bond), 121, 94. Anal. calcd. for C14H11NO3: C, 69.70; H,
4.60; N, 5.81. Found: C, 69.48; H, 4.84; N, 5.68.
Benzophenone O-Phenyl Oxime (3k)
1
Colorless oil. IR (KBr): 3058, 1592, 1487, 1214, 929, 753, 694 cmꢀ1. H
NMR (300 MHz, CDCl3) d: 7.61–7.58 (m, 2H), 7.47–7.22 (m, 12H), 7.01
(t, 1H). 13C NMR (75 MHz, CDCl3) d: 159.9, 159.5, 135.9, 132.8, 129.9,
129.3, 129.2, 128.4, 128.3, 128.0, 122.2, 114.8. MS (EI): m=z ¼ 273[Mþ]
180 (fission of the N-O bond), 77, 65, 51, 39. Anal. calcd. for
C19H15NO: C, 83.49; H, 5.53; N, 5.12. Found: C, 83.35; H, 5.38; N, 5.16.
4-Nitrobenzaldehyde O-Phenyl Oxime (3l)
Light yellow solid. IR (KBr): 1583, 1517, 1485, 1343, 1215, 944, 849, 152,
1
689 cmꢀ1. H NMR (300 MHz, CDCl3) d: 8.48 (s, 1H), 8.30–8.28 (d,
J ¼ 8.7 HZ), 7.90–7.88 (d, J ¼ 8.7 Hz), 7.39–7.34 (t, 2H), 7.28–7.26 (d,
J ¼ 8.1 Hz, 2H), 7.12–7.10 (t, 1H). 13C NMR (75 MHz, CDCl3) d:
158.9, 149.2, 137.5, 129.5, 128.2, 124.1, 123.0, 114.6, 109.7. MS (EI):
m=z ¼ 242 [Mþ], 149 (fission of the N-O bond), 94, 76, 65, 50, 39. Anal.
calcd. for C13H10N2O3: C, 64.46; H, 4.16; N, 11.56. Found: C, 64.40;
H, 4.24; N, 11.41.

1778
X.-H. Feng et al.
ACKNOWLEDGMENT
We gratefully thank the State Key Laboratory of Applied Organic Chem-
istry for financial support.
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