Selective Oxidation of Aromatic Olefins Catalyzed by Copper(II) Complex in Micellar Media

Article abstract of DOI:10.1007/s10562-017-2160-z

Abstract: The selective oxidation of aromatic olefins 1,2-dimethoxy-4-vinylbenzene (DEVB) and 2-methoxy-4-vinylphenol (MOVP) by H₂O₂ into 1-(3,4-dime-thoxyphenyl)ethanol (MVA) and 1-(4-hydroxy-3-methoxyphenyl)ethanol (HMOPE) catalyzed by copper(II) complex CuL (L = 6,8,15,17-tetramethyl-7,16-dihydrodibenzo-1,4,8,11-tetraazacyclotetradecine) were achieved in cationic surfactant cetyl trimethylammonium bromide (CTAB), anionic surfactant sodium dodecyl benzene sulfonate (SDBS) and nonionic surfactant Triton X-100 (TX-100) micellar media, respectively. Micelle showed great influence on both reaction rate and selectivity of product. Aromatic olefins could be oxidized into corresponding aromatic ketones in aqueous solution, but into secondary alcohols in micellar media. The combination of TEMPO and CuL/H₂O₂ resulted in relatively fast reaction rate and S > 96% selectivity of aromatic ketones. The reaction rate constants, k₁, k₂ and k₃ for three oxidation reactions pathways: olefin to ketone, olefin to alcohol and alcohol to ketone were obtained, respectively. The kinetic study indicated that the CuL catalyzed oxidation of olefins by H₂O₂ to alcohols was a relatively rapid and major reaction and ketone was generated by the direct oxidation of olefins, not by further oxidation of alcohol in micellar media. Graphical Abstract: [Figure not available: see fulltext.].

Full text of DOI:10.1007/s10562-017-2160-z

Catal Lett
DOI 10.1007/s10562-017-2160-z
Selective Oxidation of Aromatic Olefins Catalyzed by Copper(II)
Complex in Micellar Media
Xiao‑Hong Li1,2 · Chun Mi · Xiao‑Hong Liao · Xiang‑Guang Meng
1
1
1
Received: 5 June 2017 / Accepted: 30 July 2017
©
Springer Science+Business Media, LLC 2017
Abstract The selective oxidation of aromatic olefins
be oxidized into corresponding aromatic ketones in aque-
ous solution, but into secondary alcohols in micellar media.
The combination of TEMPO and CuL/H O resulted in rela-
1
4
,2-dimethoxy-4-vinylbenzene (DEVB) and 2-methoxy-
-vinylphenol (MOVP) by H O into 1-(3,4-dime-thoxy-
2
2
2
2
phenyl)ethanol (MVA) and 1-(4-hydroxy-3-methoxyphenyl)
ethanol (HMOPE) catalyzed by copper(II) complex CuL
tively fast reaction rate and S>96% selectivity of aromatic
ketones. The reaction rate constants, k , k and k for three
1
2
3
(
L = 6,8,15,17-tetramethyl-7,16-dihydrodibenzo-1,4,8,11-
oxidation reactions pathways: olefin to ketone, olefin to alco-
hol and alcohol to ketone were obtained, respectively. The
kinetic study indicated that the CuL catalyzed oxidation of
olefins by H O to alcohols was a relatively rapid and major
tetraazacyclotetradecine) were achieved in cationic sur-
factant cetyl trimethylammonium bromide (CTAB), anionic
surfactant sodium dodecyl benzene sulfonate (SDBS) and
nonionic surfactant Triton X-100 (TX-100) micellar media,
respectively. Micelle showed great influence on both reac-
tion rate and selectivity of product. Aromatic olefins could
2
2
reaction and ketone was generated by the direct oxidation of
olefins, not by further oxidation of alcohol in micellar media.
Electronic supplementary material The online version
of this article (doi:10.1007/s10562-017-2160-z) contains
supplementary material, which is available to authorized users.
*
Xiang-Guang Meng
mengxgchem@163.com
1
Key Laboratory of Green Chemistry and Technology,
Ministry of Education, College of Chemistry, Sichuan
University, Chengdu 610064, People’s Republic of China
2
School of Pharmaceutical Engineering, Guizhou Institute
of Technology, Guiyang 550003, People’s Republic of China
Vol.:(0
1
123456789)
3

X.-H. Li et al.
Graphical Abstract
Keywords Catalysis · Selective oxidation · Aromatic
epoxidations of alkenes catalyzed by (salen)Mn(III) in aque-
ous surfactant systems [31]. Broeke et al. reported the epoxi-
dation of 1-octene and propene with hydrogen peroxide in
micellar media [32]. Heijnen et al. used micelle-incorporated
porphyrin catalysts to catalyze linear terminal alkenes to
epoxy compound [33]. In recent study [34], we observed
a structurally similar copper(II) complex LCu can catalyze
the oxidation of terminal olefins by H O to aldehydes with
olefins · Micelle · Kinetics
1
Introduction
Functionalization of olefin is critical in organic synthesis
and pharmaceutical industries [1]. In recent years, there has
been some reports about oxidations of olefins. However,
most reports focus on the oxidations of olefins to epoxide
2
2
high selectivity (S>90%) in CH CN. In this work, for the
3
copper(II) complex CuL catalyzed systems, it was found
that micelles showed great effect on both reaction rate and
selectivity of product. Highly selective oxidations of aro-
matic olefins by H O to aromatic secondary alcohols were
[
2–7], aldehydes [8–10] and aromatic acids [11]. In the clas-
sical Wacker oxidation reaction, the terminal olefins were
transformed into aldehydes or methyl ketones by using Pd
2
2
achieved in micellar media.
as catalyst and O as oxidant [12–18]. But the yield and
2
selectivity are often low. The oxidant and the oxidative
species have important influence on oxidation reactions.
Benzoquinone, tert-butyl hydroperoxide, oxygen, iodosylb-
enzene and tetra-n-butylammonium hydrogen monopersul-
fate have been used as oxidants to oxidize olefin [19–22].
2 Experimental Section
2.1 Materials
2
,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO), a typical
N–O radical, is an excellent oxidant and was widely applied
in oxidation of organic compounds owing to the advantage
of reaction selectivity and mild conditions [23, 24]. How-
ever, study on oxidation of olefin by TEMPO was hardly
reported. In previous studies, we found that the “copper
complex associative radical CuL–·OOH” species could be
readily generated through the oxidation of copper complex
CuL by H O and displayed excellent oxidation ability for
CuCl ·2H O, 30% hydrogen peroxide, acetylacetone, o-phe-
2
2
nylenediamine, 3,4-dimethoxy acetophenone (DMOAP),
1-(3,4-dimethoxyphe-nyl)ethanol (MVA), TEMPO, sodium
dodecyl benzene sulfonate (SDBS), cetyl trimethylammo-
nium bromide (CTAB), Triton X100 (TX-100) were all
analytical grade and purchased from commercial sources.
1-(4-hydroxy-3-methoxyphenyl)ethanone (HMOPEN) and
1-(4-hydroxy-3-methoxyphenyl)ethanol (HMOPE) were
synthesized according to literatures [20, 21]. All other
chemicals and solvents used were analytical grade with to
some extent purification.
2
2
aromatic compounds [25, 26]. Surfactant and its micelle can
alter reaction rate, mechanism, region- and stereochemistry
[
27–30]. Recently Ballistreri et al. studied enantioselective
1
3

Selective Oxidation of Aromatic Olefins Catalyzed by Copper(II) Complex in Micellar Media
2
.2 Instruments and Methods
3 Results and Discussion
Ultraviolet–visible absorbance measurements were per-
formed with a spectrophotometer (Hitachi U-2910, Japan).
Elemental analyses were implemented with an elemental
analyzer (MOD 1106, Carlo Erba Company of Italy). The
3.1 Catalytic Oxidation of Olefins
In this work, the oxidation of aromatic olefins 1a and 2a by
H O to secondary alcohols and ketone in the presence of
2
2
−
1
typical reaction solution containing 0.01 mol L olefin,
CuL, TEMPO–CuL or TEMPO were investigated at 40 °C,
respectively (Scheme 1). The concentrations of alcohols,
ketones and olefins in reaction solution were quantitatively
detected by GC and HPLC (Fig. S2). The olefins 1a, 2a
were oxidized by H O to corresponding secondary alco-
−
1
−1
0
.004 mol L copper(II) complex and 0.2 mol L H O
2 2
was sealed and reacted at pH 2 and 40 °C. The concentra-
tions of reaction reactants and products in the reaction
solution were quantitatively detected by HPLC and GC.
The reaction solution was analyzed by GC (FULI 9790,
China), GC–MS (Agilent 5973 Network 6890 N, Japan)
and HPLC (waters 1525, USA) with a UV–vis detector
2
2
hols MVA, HMOPE catalyzed by CuL complex in CTAB,
SDBS, TX-100 and aqueous solution, respectively (Table 1).
From Table 1, it is noted that high selectivity (S>90%) of
secondary alcohols 1c and 2c could be achieved when the
oxidation reaction carried out in micellar media. Compared
with in micellar media, only 6.1 and 6.9% of selectivity of
1c and 2c could be found in aqueous solution, respectively,
which indicated that the CuL complex displayed excellent
catalytic ability for the oxidation of 1a, 2a to secondary
alcohols in the micellar media. 2,2,6,6-tetramethylpiperidine
1-oxyl (TEMPO), a typical N–O radical, was widely applied
in oxidation of organic compounds owing to the advantage
of reaction selectivity and mild conditions. In order to inves-
tigate the effect of TEMPO, we introduce TEMPO to this
reaction. It should be noted that the reaction rate was obvi-
ously accelerated and selectivity also changed when TEMPO
participated in the oxidation reaction (Table 2). As can be
seen from Table 2, the 100% conversion of substrates and
over 95% selectivity of ketones could be observed when both
CuL complex and TEMPO existed (Table 2, entries 5–8).
Especially, it can be seen that the olefins can be oxidized
into ketones with 100% selectivity in CuL-TEMPO associ-
ated system in aqueous solution (Table 2, entry 5). As seen
in Tables 1 and 2, micelle medium can change the reaction
rate as well as the selectivity of product. The aromatic sec-
ondary alcohols were the chief products (S> 90%) in the
CuL–H O system in micellar media (Table 1, entries 2–4).
(
detected at λ = 254 nm).
2
.3 Preparation of Copper(II) Complex
The ligand 6,8,15,17-tetramethyl-7,16-dihydrodibenzo-
1
,4,8,11-tetraazacyclotetrade-cine (L) and copper(II)
complex CuL was prepared, purified and characterized
as described in the literature [22]. Analysis: Anal. calcd.
for C H N Cu: C, 64.76; H, 5.93 N, 13.73%; found:
2
2
24
4
C, 64.81; H, 5.90; N, 13.75%; ICP-AES analysis for Cu:
1
5.56 wt%. The chemical structure of copper(II) complex
was outlined in Fig. 1S in supporting information.
2
.4 Synthesis of Substrates DEVB and MOVP
1
,2-dimethoxy-4-vinylbenzene (DEVB) was synthesized
as follows: DMOAP (1.76 g) was added to absolute metha-
nol (20 mL), then sodium borohydride (0.88 g) was added
slowly into the mixture and the solution was stirred for
4
h under ice water bath. Then the reaction solution was
refluxed for 10 h. The suspension gradually became a clear
solution, then it was adjusted to pH 3.0 with hydrochlo-
ric acid. The solvent was removed by vacuum distillation
then the reaction mixture was poured into iced water (20
mL) and extracted with 1,2-dichloroethane. The extract
was eluted with the mixture of ethyl acetate and n-hexane
in 1:1 (v/v) and then distilled to obtain the product DEVB.
It was determined by elemental analysis and GC/MS.
m/z: 164, 149, 121, 103, 91, 77, 65, 51, Anal. Calcd. for
C H O : C, 73.15; H, 7.37%; found: C, 73.17; H, 7.36%.
2
2
However, when TEMPO was used as oxidant, lots of aro-
matic ketone generated in micellar solution (Table 2, entries
2–4). Further, it can be observed that when this reaction
was carried out in aqueous solution, the main product was
aromatic ketone (Table 1, entry 1; Table 2 entries 1 and 5).
This implies that the oxo species could play important role
in the oxidation reaction. Catalyst CuL, as a cheap transition
metal complex, can activate hydrogen peroxide to generated
“associated radical CuL–·OOH”, which was described in
our previous studies [25, 26]. TEMPO can oxidize alcohol
to ketone. Further we found the complex CuL can catalyze
the reduction state TEMPOH to oxidation form TEMPO in
the presence of H O . Therefore in the presence of TEMPO,
1
0
12
2
The compound of 2-methoxy-4-vinylphenol (MOVP)
was similar to the method of DEVB synthesis. It was deter-
mined by elemental analyses. Anal. Calcd. for C H O : C,
9
10
2
7
1.98; H, 6.71%; found: C, 72.02; H, 6.70%.
2
2
CuL catalyzes the reduced TEMPOH back to TEMPO, this
greatly accelerated the conversion from alcohol to ketone,
1
3

X.-H. Li et al.
DEVB
MVA
DMOAP
(
a )
1
0
8
6
4
2
0
1
MOVP
1
0
8
6
4
2
0
(a2)
HMOPE
HMOPEN
0
2
4
6
8
10
0
2
4
6
8
10
t/h
t/h
1
0
8
6
4
2
0
1
0
8
6
4
2
0
(
b )
MOVP
HMOPE
HMOPEN
(
b )
2
1
DEVB
MVA
DMOAP
0
2
4
6
8
10
0
2
4
6
8
10
t
/h
t/h
1
0
8
6
4
2
0
10
8
(
c )
(
c )
2
MOVP
HMOPE
HMOPEN
1
DEVB
MVA
DMOAP
6
4
2
0
0
2
4
6
8
10
0
2
4
6
8
10
t/
h
t/h
−
1
−1
Fig. 1 The variations of concentration c of olefins, ketones and
alcohols versus time t, a and a in CTAB micellar media: b and
c (olefin)=0.01 mol L , c(H O )=0.2 mol L , c(CuL)=0.004
0 2 2
−1
mol L , solid line theoretical fitting curves based on the Eqs. (5) to
1
2
1
b
in SDBS micellar media: c and c in TX-100 micellar media,
(7) in supporting information
2
1
2
so that the final mainly product was ketone. The experimen-
tal results also indicate indirectly that the oxo species of
CuL–·OOH possesses different oxidative properties from
TEMPO radical. In order to clarify the reaction pathway,
we carried out the oxidation of MVA and HMOPE under
the same reaction conditions, and found that the rates of
oxidation of MVA to DMOAP and HMOPE to HMOPEN
were very slow. The conversion MVA to DMOAP was <3%
and that of HMOPE to HMOPEN was <4.6% after 12 h in
micellar media. This indicated that the generated aromatic
ketone might not be caused mainly by the oxidation of aro-
matic alcohol. Thus two parallel reaction pathways were
1
3

Selective Oxidation of Aromatic Olefins Catalyzed by Copper(II) Complex in Micellar Media
CH3
HO
CH3
O
O
OH
k3
CuL
+
k2
OCH3
H2O2
OCH3
H3CO
OCH3
OCH3
R
R
R
R
R
OCH3
O
R = OCH3 1a
1b
2b
1c
2c
R
k1
R = OH
2a
R=OH, OCH3
OCH3
R
Scheme 1 Catalytic oxidation of aromatic olefins to secondary alco-
hols and ketone
Scheme 2 The reaction pathways proposed for aromatic olefins oxi-
dation
suggested: aromatic olefins could be oxidized to not only
ketones but also alcohols. The possible reaction pathways
were suggested as illustrate in Scheme 2.
seen in Fig. 4S in supporting information. This indicated that
they were also first-order with respect to the concentrations
of alcohols. The k calculated from the one step oxidation
3
3
.2 Reaction Kinetics
reaction were listed in Table 1S in supporting information
and it can be seen that the values of k were approximately
3
To understand the mechanism of CuL-catalyzed olefins oxi-
dation reaction, the reaction kinetics was investigated. In
this work, we employed excessive concentration of H O
consistent with those of the overall reactions in Table 3.
From the calculated rate constants k , k and k of oxidations
1
2
3
of DEVB and MOVP with H O catalyzed by CuL complex,
2
2
2
2
over that of olefins or that of alcohols to carry out the reac-
tion in CTAB, SDBS and TX-100 micelles, respectively. The
variations of the measured concentrations of olefins, ketones
and alcohols with reaction time were showed in Fig. 1.
According to the proposed reaction pathways (Scheme 2),
Eqs. (1)–(10) can be deduced in supporting information.
From Eqs. (4) to (7) in supporting information, the reaction
it is noted that k was small, and k was much greater than
3 2
k in micellar medium. This means that the oxidation of ole-
1
fins to alcohols with H O catalyzed by CuL was relatively
2
2
fast and it was a predominant reaction pathway in kinetics
in micellar medium. This indicated that the Scheme 2 was
reasonable. For the power orders α, β and γ, the values were
approximately equal to 1, this meant that the reactions of
olefin to alcohol, olefin to ketone and alcohol to ketone were
all first order with respect to the concentration of H O .
∗
ꢀ
ꢀ
ꢀ
rate constants k , k , k and k can be obtained by fitting the
1
2
3
experimental data in Fig. 1. From Fig. 1, it can be seen that
the theoretical curves were in good agreement with experi-
mental data. The multiple correlation coefficients were all
more than 0.98. Thus from Eqs. (8) to (10) in supporting
information, the values of k , k , k , α, β and γ were obtained
2
2
4 Conclusions
1
2
3
by fitting the straight lines of lnk′ versus lnc (Figs. 3S to 5S
In summary, the oxidation reactions of aromatic ole-
fins DEVB and MOVP in CuL–H O , TEMPO,
P
in supporting information). The calculated results were listed
in Table 3. To better understand the comprehensive reaction
kinetics, we carried out alone the “one step” oxidation reac-
tions of alcohols (MVA, HMOPE) with H O in CuL cata-
2
2
TEMPO–CuL–H O systems were investigated in detail. A
2
2
novel method that highly selective oxidation of aromatic ole-
fins with H O into aromatic secondary alcohols catalyzed
2
2
2
2
lyzed system. It was found that ln(c (alcohol)/c (alcohol))
by CuL in micellar medium, was developed. This is the first
0
t
versus reaction time t were all straight lines (r> 0.99), as
example for the oxidation of aromatic olefin to aromatic
Table 1 Oxidation of styrene
Entry
Medium
Time/h
Conv. (%) of
Sel. (%) of
derivatives 1a and 2a by H O
2
2
catalyzed by CuL complex in
1a
2a
1b
1c
6.1
91.7
91.4
91.9
2b
2c
6.9
90.4
93.4
91.1
various systems
1
2
3
4
H O
18
12
12
12
80
78
81
72
83
80
88
82
93.8
7.1
7.6
6.8
92.9
8.2
6.5
7.8
2
CTAB
SDBS
TX-100
c (1a or 2a)=5×10 mol L , c(H O )=0.02 mol L , c(CuL)=5×10 mol L−1, c(CTAB)=0.01
−
4
−1
−1
−1
−3
−5
0
2
2
−1
−1
mol L , c(SDBS)=0.012 mol L , c(TX-100)=3.3×10 mol L , pH 2.0, 40 °C
1
3

X.-H. Li et al.
Table 2 Oxidation of styrene
derivatives 1a and 2a in the
presence of TEMPO in various
systems
Entry
Reaction system
Medium
Time/h
Conv. (%) of
Sel. (%) of
1a
2a
1b
1c
2b
2c
1
2
3
4
5
6
7
8
TEMPO
TEMPO
TEMPO
TEMPO
TEMPO–CuL/H O
TEMPO–CuL/H O
H O
18
12
12
12
7.5
4
86
100
92
88
100
91
97.7
45
2.3
55
55.4
58.8
0
<1
<2
3.8
97.1
48
2.1
52
53.4
57.5
0
<1
<2
3.1
2
CTAB
SDBS
TX-100
43.8
41.2
100
>99
>98
96.2
46.3
42.2
100
>99
>98
96.8
85
88
H O
100
100
100
100
100
100
100
100
2
2
2
2
2
2
CTAB
SDBS
TX-100
2
TEMPO–CuL/H O
TEMPO–CuL/H O
3
4
2
2
−
4
−1
−1
−3
−5
c (1a or 2a)=5×10 mol L , c(H O )=0.02 mol L , c (TEMPO)=2×10 M, c(CuL)=5×10
0
2
2
0
−1
−1
−1
−3
−1
mol L , c(CTAB)=0.01 mol L , c(SDBS)=0.012 mol L , c(TX-100)=3.3×10 mol L , pH 2.0,
4
0 °C
Table 3 The calculated
k1 (M−β·h−1
k2 (M−α·h−1
103k (M−γ·h−1
Solvent
)
)
)
α
β
γ
3
reaction rate constants k , k , k
3
1
2
and the powers orders α, β, γ for
DEVB
MOVP
CTAB
SDBS
TX-100
CTAB
SDBS
TX-100
0.081
0.11
0.075
0.10
0.13
0.085
0.51
0.57
0.47
0.57
0.60
0.48
0.80
1.12
0.75
0.85
1.36
0.81
1.12
1.07
1.05
1.08
1.11
1.08
1.09
1.12
1.04
1.12
1.06
1.06
1.15
1.10
1.14
1.14
1.06
1.15
the oxidation of olefins by H O
2
2
catalyzed by CuL complex at
pH 2.0 and 40 °C
secondary alcohol catalyzed by transit metal complex in
high selectivity (S>90%) under mild conditions in micel-
lar medium. The complex CuL can catalyze the reduction
form TEMPOH to oxidation form TEMPO in the presence of
H O . The combination of TEMPO and CuL–H O resulted
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catalyzed system, oxidation of olefins by H O to alcohols
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