Highly efficient oxidative cleavage of carbon-carbon double bond over meso-tetraphenyl cobalt porphyrin catalyst in the presence of molecular oxygen

Article abstract of DOI:10.1002/cjoc.201200621

Highly efficient and selective carbon-carbon double bond aerobic cleavage of olefins catalyzed by metalloporphyrins was investigated, and carbonyl compounds and epoxide were produced as the main products. CoTPP (cobalt meso-tetraphenyl porphyrin) showed excellent activity for the oxidative cleavage of carbon-carbon double bond by using styrene as model compound, in which the TOF (turnover frequency) and selectivity toward benzaldehyde was obtained with 2×10⁴ h^-1 and 86%, respectively.

Full text of DOI:10.1002/cjoc.201200621

FULL PAPER
DOI: 10.1002/cjoc.201200621
Highly Efficient Oxidative Cleavage of Carbon-Carbon Double
Bond over meso-Tetraphenyl Cobalt Porphyrin Catalyst in
the Presence of Molecular Oxygen†
Zhou, Xiantai(周贤太)
Ji, Hongbing*(纪红兵)
School of Chemistry and Chemical Engineering, Key Laboratory of Low-Carbon Chemistry & Energy
Conservation of Guangdong Province, Sun Yat-sen University, Guangzhou, Guangdong 510275, China
Highly efficient and selective carbon-carbon double bond aerobic cleavage of olefins catalyzed by metallopor-
phyrins was investigated, and carbonyl compounds and epoxide were produced as the main products. CoTPP (co-
balt meso-tetraphenyl porphyrin) showed excellent activity for the oxidative cleavage of carbon-carbon double bond
by using styrene as model compound, in which the TOF (turnover frequency) and selectivity toward benzaldehyde
was obtained with 2 104 h－1 and 86%, respectively.
×
Keywords oxidative cleavage, metalloporphyrins, molecular oxygen, carbon-carbon double bond
Introduction
glycol) modified metalloporphyrins were used as cata-
lyst for the oxidative cleavage of alkenes with sodium
periodate as oxidant.[9] The oxidation of styrene in the
presence of aldehydes and anion metalloporphyrins was
reported by Haber group. By using Co-T(p-SO3H)PP
porphyrin (CoTPPS) as homogeneous catalyst, the TOF
Oxidative cleavage of carbon-carbon double bond to
form carbonyl compounds is an important functional
group transformation. Ozonolysis, in general, is used for
this transformation. However, ozone is explosive and
the special equipment is necessary to fulfill such trans-
formation. From economic and environmental view-
points, catalytic oxidation processes with molecular
oxygen or air are extremely valuable and particularly
attractive. Accordingly, variety of transition or noble
metal based catalysts (mainly cobalt,[1] vanadium,[2]
copper,[3] ruthenium[4] and palladium[5]) have been in-
tensively investigated for aerobic oxidative cleavage of
C＝C bond so far. These catalysts present good cata-
lytic activities, but often suffer from not so good yields
of carbonyl compounds as products. Therefore, the de-
velopment of alternative protocols to increase the selec-
tivity of oxidative cleavage product is of great signifi-
cance.
and selectivity of benzaldehyde were 57 h－ and 66%,
1
respectively.[10]
We ever noticed the cytochrome P-450 model cata-
lysts was efficient for the aerobic oxidative cleavage of
C＝C bond of cinnamaldehyde to benzaldehyde under
ambient conditions.[11] In continuation of our ongoing
research on the metalloporphyrins-based oxidations and
gaining insight into the reaction of aerobic oxidative
cleavage of C＝C bond, we report herein the efficient
oxidative cleavage of alkenes under mild conditions by
using styrene as model substrate (Scheme 1). Compar-
ing with CoTPPS catalyst, cobalt porphyrin (CoTPP)
proved to be a more effective catalyst with extremely
－
1
high TOF (2×104 h ) and excellent selectivity of ben-
In recent years, metalloporphyrins have been used as
cytochrome P-450 models and have been found to be
highly efficient homogeneous or heterogeneous cata-
lysts for the oxidation reactions of organic compounds.[6]
Although great efforts have been made to develop the
various metalloporphyrins-catalyzed oxidations,[7] few
reports could be found for the oxidative cleavage of
carbon-carbon double bond in the presence of metal-
loporphyrins. Guo et al.[8] ever reported the aerobic
oxidative cleavage of styrene catalyzed metallopor-
phyrins in high pressure and temperature. Poly(ethylene
zaldehyde (86%).
Experimental
Materials and instruments
All chemical reagents were of analytical grade and
obtained without further purification unless indicated.
Pyrrole and isobutyraldehyde were redistilled before use.
Metalloporphyrins catalysts were prepared according to
the previous procedures.[12] The structures of catalysts
were confirmed by elementary analysis, IR spectra and
*
E-mail: jihb@mail.sysu.edu.cn; Tel.: 0086-020-84113658; Fax: 0086-020-84113654
Received July 1, 2012; accepted August 27, 2012.
Dedicated to the 80th Anniversary of Chinese Chemical Society.
†
Chin. J. Chem. 2012, 30, 2103—2108
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Zhou & Ji
FULL PAPER
Scheme 1 Aerobic oxidation of styrene catalyzed by metallo-
porphyrins
Table 1 Oxidative cleavage of styrene catalyzed by various
metalloporphyrins catalysts in the presence of molecular oxygena
Selectivity/%
Metalloporphyrins (a-d)
Entry Catalyst
Conv./%
Benzotrifluoride, isobutyraldehyde, O2 (1 atm), 80 oC
O
1
2
1
2
3
4
5
6
FeTPPCl
MnTPPCl
RuTPPCl
CoTPP
＞99
＞99
82
59
54
57
86
88
85
41
46
43
14
12
15
O
+
2
1
＞99
＞99
＞99
CoTNPP
CoTCPP
－
a Catalyst (1×10 mmol), styrene (1 mmol), benzotrifluoride (5
mL), isobutyraldehyde (3 mmol), O2 (bubbling), 80 ℃, 5 h.
5
N
N
N
N
M
catalytic activity for the cleavage oxidation of styrene.
The selectivity toward benzaldehyde and epoxide of the
system depends on the type of metal in macrocyclic
rings (Entries 1—4). The present results clearly show
that cobalt porphyrins are considerably more selective
than manganese, iron and ruthenium porphyrins cata-
lysts for the oxidative cleavage of C＝C bond. This
phenomenon may be connected with the fact that the
intermediates generated from cobalt complexes are
more stable than that from other metal complexes.[13] It
was well reported that electron-withdrawing substitu-
ents on the porphyrin ring had positive effect on the
activity for the hydroxylation, in which the substituent
could deplete electron density at the metal center.[14]
Therefore, cobalt porphyrin with ortho-position elec-
tron-withdrawing substituents (tetra-(o-nitrophenyl)
cobalt porphyrin, tetra-(o-chlorphenyl) porphyrin cobalt
porphyrin, abbreviated as CoTNPP and CoTCPP re-
spectively) were used for the oxidative cleavage of C＝
C bond by molecular oxygen in the presence of isobu-
tyraldehyde. Unfortunately, no significant enhancement
of the selectivity was observed in the catalytic system
(Entries 5 and 6), indicating that the mechanism of the
oxidative cleavage of C＝C bond was different from
that of C-H hydroxylation. Therefore, simple cobalt
porphyrin (CoTPP), the most selective among the stud-
ied catalysts, was chosen for further investigations.
Central metal ions M: (a) Fe; (b) Mn; (c) Ru; (d) Co
UV-Vis spectra.
UV-Vis spectra were recorded on a Shimadzu
UV-2450 UV-Vis spectrophotometer. FT-IR spectra
were obtained on a Bruker 550 spectrometer. Elemental
analysis data were obtained on Vario EL III.
General procedure for the oxidative cleavage of C＝
C bond
A 20 mL Schlenck tube equipped with a condensing
unit was charged with styrene (1 mmol), metallopor-
phyrins catalyst (1×10－ mmol), benzotrifluoride (5
5
mL), isobutyraldehyde (3 mmol), naphthalene (inert
internal standard, 0.8 mmol) and then the mixture was
stirred at 80 ℃. Dioxygen was bubbled through the
solution. The consumption of the starting styrene and
formation of products were monitored by GC (Shima-
dzu GC-2010 plus) or GC-MS (Shimadzu GCMS-
QP2010). The product yields were based on the amount
of alcohols consumed in the reactions. All reactions
were conducted within the experimental error±5%.
Results and Discussion
Effect of the amount of catalyst on the oxidative
cleavage of C＝C bond
Catalytic performance of metalloporphyrins for the
oxidative cleavage of C＝C bond
Table 2 shows the influence of catalyst amount on
the oxidative cleavage of styrene in the presence of mo-
lecular oxygen and isobutyraldehyde.
For the initial studies on the catalytic activity of
metalloporphyrins in the oxidative cleavage of carbon-
carbon double bond with dioxygen, styrene was used as
a model substrate to assess their catalytic properties in
this reaction. Iron, manganese, cobalt and ruthenium
were the most frequently used metals in oxidation reac-
tions and those metals were chosen to synthesize simply
structural metalloporphyins. The oxidation of styrene
catalyzed by these catalysts produced benzaldehyde and
epoxide as the main products. The catalytic results are
given in Table 1.
As shown in Table 2, almost no reaction was ob-
served in the blank experiment even the reaction time
was prolonged to 8 h (Entry 8). The conversion of sty-
rene was considerably enhanced when the cobalt por-
phyrin catalyst was used. That cobalt porphyrin was
crucial in the reaction could be demonstrated from the
fact that the conversion of styrene could reach up to
85% even the amount of catalyst was only 5.0×10－
6
mmol (Entry 7). As depicted clearly in Table 2, the re-
action rate increased with the increasing catalyst con-
From Table 1, metalloporphyrins showed excellent
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Chin. J. Chem. 2012, 30, 2103—2108

Oxidative Cleavage of Carbon-Carbon Double Bond over meso-Tetraphenyl Cobalt Porphyrin Catalyst
Table 2 Effect of the amount of catalyst on the oxidative cleav-
mally influenced by reaction temperature, but the selec-
tivity of products was closely related with the reaction
temperature. It seems that low temperature was favor-
able for the epoxidation of styrene, while high reaction
temperature was favorable for the oxidative cleavage of
C＝C bond. When the temperature was 40 ℃, the yield
of epoxide was 89%, and the yield of benzaldehyde was
only 11%. The selectivity of benzaldehyde increased
with increasing reaction temperature. The yield of ben-
zaldehyde reached as high as 86% when the reaction
was carried out at 80 ℃. The results indicated that the
epoxidation was conducted more likely at lower tem-
perature and the cleavage of C＝C competed more fa-
vorably against epoxidation at higher temperature.
Higher temperature might be favorable for the radical
chain reaction (one electron transferred), leading to the
formation of benzaldehyde.
age of styrenea
Selectivity/%
Amount of
catalyst/mmol
1
Entry
TOF/h－
Conv./%
1
2
1
2
3
4
5
6
7
8b
1.0×10－
5.0×10－
3.0×10－
1.0×10－
5.0×10－
1.0×10－
5.0×10－
0.2×103 ＞99
0.4×103 ＞99
0.67×103 ＞99
0.2×104 ＞99
0.4×104 ＞99
2.0×104 ＞99
3.4×104 85
53
51
56
58
69
86
62
32
47
49
44
42
31
14
38
68
3
4
4
4
5
5
6
0
—
5
a Styrene (1 mmol), catalyst (CoTPP), benzotrifluoride (5 mL),
b
isobutyraldehyde (3 mmol), O2 (bubbling), 80 ℃, 5 h. Reaction
time was 8 h.
However, a further increase of temperature to 90 ℃
exhibited a decreasing selectivity of benzaldehyde. It
was due to that the over-oxidation products (benzoic
acid, 32%) were obtained at this temperature. As seen in
Figure 1, the temperature of 80 ℃ was found optimal
for the maximum selectivity of benzaldehyde.
tents. Styrene was converted completely when the molar
ratio of the catalyst to substrate was 1/1×105 (Entry 6),
in which the selectivity toward benzaldehyde was 86%.
At the catalytic amount, the catalytic efficiency was
extremely high and the TOF of CoTPP could reach up
－
1
to 2×104 h .
The products distributions were influenced by the
amount of catalyst. Further increasing the amount of the
catalyst could not enhance the yield of benzaldehyde.
On the contrary, the increasing catalyst content is fa-
vorable for the formation of epoxystyrene. This phe-
nomenon could be attributed to the two parallel reaction
pathways leading to the formation of benzaldehyde and
epoxystyrene.
Effect of the solvent on the oxidative cleavage of C＝
C bond
It is well-known that the solvent plays an important
and sometimes decisive role in the catalytic behavior of
a catalyst. Therefore, the effect of solvents on reactivity
and selectivity was studied in the current catalytic sys-
tem.
Toluene is often applied to radical reactions because
of its reluctance to undergo radical addition, which also
indicates the benzaldehyde could be generated via a
radical chain reaction. But it is well known that toluene
is easily oxidized under oxygen atmosphere. Using
toluene as a solvent in the reaction is not adequate.
As shown in Table 3, it seemed that solvent with
large dielectric constant such as acetonitrile and isopro-
panol was not suitable for the oxidative cleavage of sty-
rene (Entries 3—6). Benzotrifluoride was more favor-
able for the selectivity of benzaldehyde in the oxidative
Effect of the temperature on the oxidative cleavage
of C＝C bond
The effect of reaction temperature on the conversion
of styrene, and the selectivity to benzaldehyde for the
oxidative cleavage of styrene catalyzed by CoTPP cata-
lyst was studied; the results were shown in Figure 1.
Table 3 Effect of the solvent on the oxidative cleavage of sty-
renea
Selectivity/%
Entry Solvent
Conv./%
1
2
1
2
3
4
5
Benzotrifluoride
＞99
＞99
91
86
52
46
18
21
16
14
48
54
82
79
84
Cyclohexane
Acetonitrile
Isopropanol
Ethanol
Figure 1 Effect of temperature on the conversion of styrene
80
(
(
), selectivity of benzaldehyde (
), selectivity of epoxide
). Reaction conditions: CoTPP (1×10－ mmol), styrene (1
5
82
mmol), isobutyraldehyde (3 mmol), benzotrifluoride (5 mL), O2
(bubbling), 5 h.
6
a
Methanol
75
－
5
CoTPP (1×10 mmol), styrene (1 mmol), solvent (5 mL),
isobutyraldehyde (3 mmol), O2 (bubbling), 80 ℃, 5 h.
From Figure 1, the conversion of styrene was mini-
Chin. J. Chem. 2012, 30, 2103—2108
© 2012 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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Zhou & Ji
FULL PAPER
Table 4 Oxidation of various substrates by molecular oxygen in
cleavage reaction (Entry 1). The three fluorine atoms of
benzotrifluoride results in better solvation effect, which
could be favorable for the generation of acylperoxy
radical.[12] Almost equal selectivity towards benzalde-
hyde and epoxide was obtained when cyclohexane was
applied as solvent in the catalytic system (Entry 2). Al-
though cyclohexane is a commonly used model sub-
strate for metalloporphyrin catalyzed oxidations,[15] no
oxidized products such as cyclohexanol or cyclohexa-
none from cyclohexane was determined for this cata-
lytic system. Lower conversion of styrene and higher
selectivity toward epoxystyrene was obtained in the
isopropanol media (Entry 4). Similar phenomenon was
observed when isopropanol was replaced by other alco-
hol solvents such as ethanol and methanol (Entries 5, 6).
the presence of CoTPPa
Entry Substrate
Time/h Conv./% Yield/%
1
5
5
5
＞99
98
86
69
85
2
Cl
3
＞99
O
4
4
4
4
6
＞99
＞99
＞99
＞99
68
65
12
58
5
Oxidative cleavage of various substrates catalyzed by
CoTPP
To evaluate the scope of the catalytic system, vari-
ous substrates were subjected to the reaction system
catalyzed by CoTPP. The results are summarized in Ta-
ble 4.
6b
7b
OH
O
As shown in Table 4, most substrates with car-
bon-carbon double bond could be smoothly converted to
the corresponding carbonyl compounds by oxidative
cleavage reaction in this catalytic system. For the sty-
rene derivatives, the oxidative cleavage of C＝C bond is
influenced by the electronic property of substrates, in
which the electron-withdrawing group seems unfavor-
able to the formation of product (Entry 3). The influence
of steric effects can be illustrated from the oxidative
cleavage of C ＝ C bond of α-methylstyrene and
β-methylstyrene. Although the substrates could be con-
verted completely in this catalytic system within 4 h, the
selectivity of benzaldehyde was only 68% and 65%
(Entries 4, 5). The steric influence is especially demon-
strated from the oxidation of trans-stilbene (Entry 6).
When the cinnamyl alcohol and cinnamaldehyde
were engaged as substrates in the catalytic system, al-
most similar selectivity of oxidative cleavage product
was obtained, in which the yields of benzaldehyde were
58% and 55%, respectively (Entries 7, 8). Similarly, in
the oxidative cleavage of linear chains e.g. trans-2-
octene, the reaction system exhibits high catalytic per-
formance with 92% yield of hexanal (Entry 9).
8b
9
6
5
＞99
＞99
55
92
a CoTPP (1×10－5 mmol), substrate (1 mmol), benzotrifluoride (5
b
mL), isobutyraldehyde (3 mmol), O2 (bubbling), 80 ℃. The
surplus product was epoxide.
Figure 2 Profile of oxidation of styrene catalyzed by CoTPP in
Plausible mechanism for the oxidative cleavage of
styrene
the presence of molecular oxygen and isobutyraldehyde. Styrene
(1 mmol), CoTPP (1×10－ mmol), benzotrifluoride (5 mL), iso-
5
The profile of the oxidative cleavage of styrene in
the presence of CoTPP, molecular oxygen and isobu-
tyraldehyde is shown in Figure 2.
As shown in Figure 2, the conversion of styrene as
well as the yields of benzaldehyde and epoxide in-
creased slowly within the first 2 hours period. After re-
acting for 2 h, the conversion of styrene and the yield of
benzaldehyde increased sharply while that of epoxide
increased slightly. It seemed that the oxidative cleavage
of styrene occurred first with induction period, and then
butyraldehyde (3 mmol), O2, 80 ℃, 5 h.
followed by sharp acceleration till completion, which
agreeed with the feature of radical-involved reaction. In
order to verify the free radical mechanism for the cata-
lytic system, a free radical inhibitor, 2,6-di-tert-butyl-
phenol (1 mmol) was added. It has been found that the
running oxidative cleavage of styrene could be subse-
quently quenched.
For substrates with carbon-carbon double bond, this
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Chin. J. Chem. 2012, 30, 2103—2108

Oxidative Cleavage of Carbon-Carbon Double Bond over meso-Tetraphenyl Cobalt Porphyrin Catalyst
Scheme 3 Possible mechanism of the aerobic oxidative cleav-
reaction may proceed in two steps involving the first
step of epoxidation and a subsequent oxidation to pro-
duce carbonyl compounds.[16] To test this mechanism,
the reactions were carried out with two epoxides,
4-methoxy styrene epoxide and styrene epoxide. How-
ever, no carbonyl products were observed in either reac-
tion (Scheme 2). Also, as shown in Figure 2, the yield of
epoxide remained almost unchanged during the reaction.
Thus, the mechanism involving epoxides as the inter-
mediates could be excluded. Such facts could strongly
indicate that the benzaldehyde and epoxystyrene are
formed along two different parallel reaction pathways.
In the aerobic epoxidation of olefins catalyzed by man-
ganese porphyrins at room temperature as reported pre-
viously,[17] high-valent metal intermediate was con-
firmed by in situ EPR and UV-vis spectrum. The oxi-
dized porphyrin metal-oxo species is known to transfer
oxygen to olefins forming epoxides.[18]
age of styrene catalyzed by cobalt porphyrin in the presence of
isobutyraldehyde
PorCoIII
RCHO
O
RCOO
PorCoII
O
O2
.
.
RC
PorCoII
Ph
B
A
.
O
O
－CoIIPor
RCO
－CH CH
－Ph
2
O
RCO
O
(a)
O2
.
O
RCOOH
O
O
PorCoIV=O
CH
RCO
－CH
O
2
Ph
(b)
PorCoII
Ph
PorCoIII
O
+
PorCoII
PhCHO + HCHO + RCOOH
Ph
Scheme 2 Aerobic oxidation of epoxides catalyzed by cobalt
porphyrins
active than manganese, iron and ruthenium porphyrins
catalysts for the oxidative cleavage of C＝C bond. By
using styrene as model compound, the TOF of CoTPP
and selectivity of benzaldehyde were obtained with 2×
O
O
O
CoTPP
Isobutyraldehyde (3 equiv.)
O
O
O
Benzotrifluoride, 80 oC, O2, 10 h
－
1
104 h and 86%, respectively. Different factors influ-
encing the oxidative cleavage of C＝C bond, such as
catalyst amount, temperature, and solvent, have been
investigated. Low catalyst content, higher temperature
and nonpolar solvent could be favorable for the oxida-
tive cleavage of C＝C bond.
<1%
In the oxidation of styrene, isobutyric acid (the
product of the oxidation of isobutyraldehyde) could be
obtained quantitatively, which indicated the reaction
was sacrificed with isobutyraldehyde. And, the oxida-
tion of styrene with dioxygen did not proceed in the
absence of isobutyraldehyde or cobalt porphyrin. The
chain reaction could be initiated by the interaction of
isobutyraldehyde with cobalt porphyrin. As described
by Haber et al.,[10] the mechanism could be illustrated as
shown in Scheme 3.
The pathway starts by the interaction of isobutyral-
dehyde with Co(III) porphyrin resulting in generation of
acyl radical. Next, acylperoxy radical is generated from
the reaction of acyl radical with molecular oxygen. A
complex radical (a) is formed by addition of acylperoxy
radical to styrene. This complex radical reacts with a
second molecule of oxygen to form another radical (b)
which picks up an electron from the porphyrin molecule
and is decomposed into benzaldehyde, isobutyric acid
and formaldehyde (pathway A). In pathway B, forma-
tion of epoxide is assumed by active high-valent Co
porphyrin intermediates, which are formed by the reac-
tion of the peroxyacid with the cobalt porphyrin.
Acknowledgements
The authors thank the National Natural Science
Foundation of China (Nos. 20976203 and No.
21036009), Higher-level Talent Project for Guangdong
Provincial Universities and the Fundamental Research
Funds for the Central Universities for providing finan-
cial support to this project.
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