Rhodium/bisphosphite catalytic system for hydroformylation of styrene and its derivatives

Article abstract of DOI:10.1002/aoc.3009

Different kinds of mono- and bidentate phosphite ligands were used in Rh-catalyzed hydroformylation of styrene to illustrate the influence of steric and electronic properties of ligands on catalytic performance. High activity (99.9%) and good regioselectivity (85.4%) to the linear aldehyde were achieved under optimum conditions in the presence of Rh/bisphosphite complex (bisphosphite: 2,2′-bis(dipyrrolylphosphinooxy)-1,1′-(±)- binaphthyl). This system makes it possible to prepare functionalized terminal aldehydes from readily available styrene or its derivatives through hydroformylation with high linear selectivity. Copyright

Full text of DOI:10.1002/aoc.3009

Full Paper
Received: 15 January 2013
Revised: 1 April 2013
Accepted: 13 April 2013
Published online in Wiley Online Library
(wileyonlinelibrary.com) DOI 10.1002/aoc.3009
Rhodium/bisphosphite catalytic system for
hydroformylation of styrene and its derivatives
a
b
a
a
a
Cong-ye Zheng , Min Mo , Hao-ran Liang , Xue-li Zheng , Hai-yan Fu ,
a
a
a
Mao-lin Yuan , Rui-xiang Li and Hua Chen *
Different kinds of mono- and bidentate phosphite ligands were used in Rh-catalyzed hydroformylation of styrene to illustrate
the influence of steric and electronic properties of ligands on catalytic performance. High activity (99.9%) and good
regioselectivity (85.4%) to the linear aldehyde were achieved under optimum conditions in the presence of Rh/bisphosphite
0
0
complex (bisphosphite: 2,2 -bis(dipyrrolylphosphinooxy)-1,1 -(ꢀ)-binaphthyl). This system makes it possible to prepare func-
tionalized terminal aldehydes from readily available styrene or its derivatives through hydroformylation with high linear se-
lectivity. Copyright © 2013 John Wiley & Sons, Ltd.
Supporting information may be found in the online version of this article.
Keywords: hydroformylation; styrene; rhodium complexes; bisphosphite
favorable for the dissociation of CO, and thereby accelerates catal-
Introduction
[
13]
ysis. Ligand (III) also has a highly Lewis acidic phosphorus atom
leading to the highest L/B ratio. It had been proved that the rho-
dium bisphosphine complexes bearing large bite angle and
containing more electron-withdrawing groups would further im-
prove the regioselectivity of linear aldehydes in the
Rhodium-catalyzed hydroformylation of olefins to corresponding
aldehydes has already been developed into one of the most im-
portant industrial processes at present.
a special hydroformylation substrate since its products, namely
branched and linear aldehydes, are quite useful. Firstly, based
on the fact that the branched aldehyde is more liable to be
yielded in the hydroformylation, styrene is usually regarded as a
model substrate for asymmetric hydroformylation. Secondly,
the linear aldehyde could be employed as an important interme-
diate in organic synthesis, such as the production of detergents,
[
1–3]
In particular, styrene is
[
14–16]
hydroformylation of olefins.
hydroformylation of styrene have been systematically investigated
The electronic effects in the
[
17]
by Vogt and co-workers, but the steric properties also played an
important role in styrene hydroformylation. Herein, we reported
the influence of steric properties through comparing ligands
containing different backbones. Several structurally similar
[
4]
[
5,6]
0
0
plasticizers and spices.
significant application potential caused researchers to investigate
the hydroformylation of styrene more thoroughly.
The fact that the linear aldehyde has
ligands – 2,2 -bis (dipyrrolylphosphinooxy)-1,1 -(ꢀ)-binaphthyl)
[18] [19]
0
2,2 -bis
BISBI
(ligand 1), BINAPO (ligand 2),
BINAP (ligand 3),
[
7–9]
[16]
0
Recently,
(dipyrrolyphosphinooxy)-1,1 -(ꢀ)-biphenyl (ligand 4),
[
20]
by using some specific ligands, linear aldehyde selectivity for
the hydroformylation of styrene has increased. For instance, Van
Leeuwen’s Xantphos derivatives (I) gave an L/B (molar ratio of
linear to branched aldehyde) ratio of 2.35 for styrene
(ligand 5)
–
and the corresponding monodentate
ligands dipyrrolyl(naphthalene-2-yloxy)phosphine (ligand 6),
[
16]
phenyldipyrrolyl phosphorus amidite (ligand 7)
and
triphenylphosphine (ligand 8) – were also been tested for com-
parison (Fig. 2).
[
7]
hydroformylation.
Sémeril and co-workers’ calixarene-based
[
8]
diphosphites (II) led an L/B ratio of up to 12.4. Zhang et al. devel-
oped a tetraphosphorus ligand (III) for styrene hydroformylation
with an L/B ratio of 22 (Fig. 1). It is generally accepted that a rho-
dium–bisphosphine complex bearing a wide bite angle can easily
form an ee configuration with the phosphorus atoms that occupy
two equatorial positions of a trigonal bipyramid, which is favorable
[
9]
Experimental
Reagents
[
10]
The solvent toluene was purified prior to use. The pressure ratio
of hydrogen (99.99%) and carbon monoxide (99.9%) was 1:1.
for the formation of the linear aldehyde (Scheme 1). Casey and
co-workers defined the ‘natural bite angle’ as the preferred chela-
tion angle, which was determined only by ligand backbone
constraints, but did not take metal valence angles into consider-
[11]
* Correspondence to: Hua Chen, Key Laboratory of Green Chemistry and Tech-
nology of Ministry of Education, College of Chemistry, Sichuan University,
Chengdu 610064, Sichuan, China. Email: scuhchen@163.com
ation. Therefore, the good results made by Xantphos derivatives
I) and calixarene-based diphosphites (II) might be related to the
(
rigid backbone. Tolman found that pyrrolyl substituents on the
phosphorus atom could form highly Lewis acidic phosphorus
a Key Laboratory of Green Chemistry and Technology of Ministry of Education,
College of Chemistry, Sichuan University, Chengdu 610064, Sichuan, China
[12]
ligands.
These ligands with strongly electron-withdrawing
groups result in lower electron density around the rhodium metal
b Key Station of Environmental Monitoring and Environmental Protection Re-
and this in turn weakens the metal–carbonyl bond, which is
search, Wanzhou 404120, Chongqing, China
Appl. Organometal. Chem. 2013, 27, 474–478
Copyright © 2013 John Wiley & Sons, Ltd.

An efficient catalytic system for the formation of linear aldehyde
R
R
N
P
N
P
N
N
O
O
N
N
O
O
OR OR
O
P
P
P
O
O
P
O
O
O
P
N
P
N
O
R
R
R=p-Tolyl
R=Fluorenyl
II
III
I
Figure 1. Structure of ligands I–III.
CDCl ) d: 149.8 (d, J = 10.6 Hz, C2 in naphthalene), 133.0
3
PC
(
(
(
s, C -C-C in naphthalene), 129.7 (s, C in naphthalene), 129.1
8 1 4
s, C -C-C in naphthalene), 126.7 (s, C in naphthalene), 126.3
4
5
5
s, C in naphthalene), 125.8 (s, C in naphthalene), 124.2 (s, C
7
8
6
in naphthalene), 120.5 (d, JPC = 15.9 Hz, PNCHCH), 119.1 (d, JPC
=
Scheme 1. Equilibrium of ee–ae configurations in rhodium trigonal bipy-
ramidal complexes.
6
.4 Hz, C in naphthalene), 114.5 (d, J = 10.8 Hz, C in naphtha-
3 PC 1
lene), 111.7 ppm (d, J PC = 4.7 Hz, PNCHCH) (see supporting
information).
Styrene (>99%) was redistilled prior to use and other reagents
[
21]
were of analytical grade. Rh(acac)(CO)2
and ligands were pre-
General Procedure of Hydroformylation
pared according to the literature and their structures were con-
1
13
31
firmed by comparing their H, C and P NMR spectra with
All the hydroformylation reactions were carried out in a stainless
steel autoclave of 60 ml with a magnetic stirrer. A toluene
[16,18–20,22]
the literature.
solution of Rh(acac)(CO) , ligand and styrene were added to the
2
autoclave, which was subsequently evacuated and purged with
syngas three times. The autoclave was then pressurized with
syngas and stirred under the specific reaction conditions. After
the reaction was completed, the vessel was cooled to room
temperature before excess syngas was carefully released. The
products were then analyzed by gas chromatography (GC;
Agilent 6890 N, with a capillary column SE-30,30 m ꢃ 0.25 mm)
and identified by GC-MS.
Synthesis of Dipyrrolyl(naphthalene-2-yloxy)phosphine (6)
[
16]
Synthesis of 6 was according to the literature. To a solution of
chlorodipyrollylphosphine (1.98 g, 10 mmol) in toluene (30 ml)
was added dropwise a mixture of 2-naphthol (1.44 g, 10 mmol)
and triethylamine (10 ml, excess) dissolved in toluene (15 ml),
with stirring at room temperature. After stirring at that tempera-
ture for 1 h, the mixture was filtered and the solution was evapo-
rated to dryness under reduced pressure to give a white solid.
The pure product was obtained by recrystallization from pentane
ꢂ
and dichloromethane at ꢁ30 C as a white solid. Yield 2.54 g
Results and Discussion
ꢂ
1
(
83%); m.p. 71 C; H NMR (400 MHz, CDCl ) d: 7.80 (d, J = 4.5 Hz,
3
1
H, C -H), 7.78 (d, J = 5.7 Hz, 1H, C -H), 7.70 (d, J = 8.0 Hz, 1H,
The electronic and steric properties of ligands in terms of their
influence on the catalyst performance were investigated. Eight
different ligands, depicted in Fig. 2, were applied in the Rh-
catalyzed hydroformylation of styrene under 1 MPa of syngas
5
8
C -H), 7.46 (m, 1H, C -H), 7.42 (m, 1H, C -H), 7.28 (s, 1H, C -H),
4
7
6
1
7
.14 (m, 5H, C -H and PNCHCH), 6.40 ppm (m, 4H, PNCHCH).
3
31
13
P NMR (162.0Hz, CDCl ) d: 107.3 ppm; C NMR (100.6 MHz,
3
N
N
P
N
N
P
P
P
N
N
O
O
O
O
PPh2
PPh2
O
O
P
N
P
N
(1)
(2)
(3)
(4)
PPh2
PPh2
N
P
N
P
P
O
N
O
N
(
5)
(6)
(7)
(8)
Figure 2. Structure of ligands 1–8.
Appl. Organometal. Chem. 2013, 27, 474–478
Copyright © 2013 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc

C.-Y Zheng et al.
a
Table 1. Effect of different ligands on styrene hydroformylation
Table 2. Ha ydroformylation of styrene with ligand 1 under different
conditions
Entry Ligand L/Rh Aldehyde
ꢀ
L/B ꢁ
Conversion of
styrene (%)
b
L
LþB
c
d
ꢂ
(%)
; %
Entry L/Rh T ( C)
p
Aldehyde
ꢀ
L/B ꢁ
; %
Conversion
of styrene
b
L
LþB
c
(
MPa) (%)
d
1
2
3
4
5
6
7
8
1
2
3
4
5
6
7
8
3
3
3
3
3
6
6
6
96.4
99.9
99.9
98.7
99.9
97.9
96.5
99.9
81.6/14.5 (84.9)
13.8/11.0 (55.6)
1.8/15.6 (10.3)
63.2/31.7 (66.6)
18.7/73.8 (20.2)
58.4/39.5 (59.7)
53.8/41.6 (56.4)
31.9/68.1 (31.9)
99.9
24.7
17.4
96.2
92.4
99.9
99.8
99.9
(%)
1
2
3
4
5
6
7
8
9
1
5
5
80
90
1
1
1
1
1
1
1
2
3
1
96.3
96.3
93.6
86.9
91.2
88.5
88.1
97.2
98.0
80.8
80.4/14.4 (84.8)
82.2/14.1 (85.4)
79.4/14.2 (84.8)
71.2/15.0 (82.6)
75.5/15.3 (83.1)
72.9/14.9 (83.0)
72.0/14.6 (83.1)
79.2/17.2 (82.2)
75.2/22.8 (76.7)
65.3/14.6 (81.7)
98.4
99.9
99.9
99.2
99.6
99.2
98.3
99.2
99.9
98.9
5
100
110
110
110
110
90
3
5
7
10
5
a
3
[
Rh] = 1.7 mmol, styrene (1.0 ml), S/C = 10 , p = 1 MPa (CO/H
2
= 1),
ꢂ
T = 80 C, t = 1 h, toluene (4.0 ml) as solvent.
5
90
b
Selectivity for aldehyde product of styrene, determined on the
basis of GC.
0
5
120
a
3
c
[
Rh] = 1.7 mmol, styrene (1.0 ml), S/C = 10 , t = 1 h, toluene (4.0 ml)
Molar ratio of linear to branched aldehyde, determined on the
basis of GC; data in parentheses present percentage of linear
aldehyde in all aldehydes.
as solvent.
b–d
See Table 1.
d
Conversion of styrene, determined on the basis of GC.
Besides electronic characters, the steric properties of ligands
can also influence the catalytic performance. Ligand 1 tends to
promote the generation of linear aldehyde in the
hydroformylation of styrene (84.9%). For comparison, ligand 4
with the biphenyl as the backbone is more flexible and thus its
rhodium complex is more liable to catalyze styrene to form the
branch aldehyde and results in a relatively lower L/B ratio of
63.2/31.7 (Table 1, entry 4) in the styrene hydroformylation. Both
1 and 4 contain the electron-withdrawing dipyrrolyl group, the
only difference being the backbone. Ligand 1 with a bulky rigid
binaphthol skeleton greatly enhances the steric hindrance
around the rhodium center and inhibits the formation of the ben-
zylic Rh species (Scheme 2b). The binaphthol skeleton favorable
for the generation of linear aldehyde was also observed in ligand
2 (Table 1, entry 2). As mentioned above, ligand containing
diphenyl phosphino group tends to afford a low L/B ratio, with
the branched aldehyde as the major product. However, ligand
2 led to a relatively higher L/B ratio (13.8/11.0), which may likely
be attributed to the bulky binaphthol backbone. The perfor-
mance of ligand 3 (Table 1, entry 3) with binaphthol skeleton still
gave a low L/B ratio, possibly due to its lower p-accepting ability.
As bidentate ligands, ligand 2 and 3 may form nine- and seven-
membered chelating rings with rhodium respectively. This
difference in coordinative mode also probably contributed to
the different regioselectivity.
ꢂ
pressure at 80 C. As demonstrated in Table 1, the ligands 1, 4, 6
and 7 containing dipyrroyl phosphino group showed better per-
formance in terms of activity and regioselectivity towards the lin-
ear aldehyde (Table 1, entries 1, 4, 6, 7). However, ligands 2, 3, 5
and 8 containing diphenyl phosphino group were favorable for
the formation of the branched aldehyde (Table 1, entries 2, 3, 5,
8
). Ligands 1 and 2 with the same bulky binaphthyl backbone
exhibited quite different performances referring to regioselectivity
and activity. For ligand 1 a good L/B ratio of 81.6/14.5 as well as
high activity (99.9%) was obtained. In contrast, only lower activity
24.7%) and linear aldehyde regioselectivity (55.6%) could be
achieved, while ligand 2 was applied in the catalysis (Table 1, entry
). The electron-withdrawing properties of the pyrrolyl group give
the ligand good p-accepting ability, which is favorable for linear
aldehyde regioselectivity in either linear olefin or styrene
hydroformylation.
ity and activity caused by ligand 1 were attributed to the presence
of electron-withdrawing pyrrolyl group. Analogously, it can be seen
that ligand 4 containing the pyrrolyl group exhibited a higher L/B
ratio than ligand 5. Although both are structurally closely related
biphenyl-substituted diphosphine ligands, there is also another
obvious structure difference between ligands 4 and 5. That is, the
P atom in ligand 4 is connected with biphenyl backbone via atom
(
2
[9,17,22,23]
Therefore, the relatively higher selectiv-
O, while in ligand 5 it is connected through CH . Van der Slot and
To further explore the backbone impact, the corresponding
monophosphine ligand 6 was also tested under the same condi-
tions to that of ligand 1. The input amount of ligand 6 was dou-
bled to ensure the catalytic system has the same phosphorus
concentration as the system using ligand 1. However, only an
L/B ratio of 58.4/39.5 was obtained, which is much lower than
2
co-workers have proved that the P-O bond can give a lower
[
16]
electronic density of phosphorus compared with P-C bond. This
difference is perhaps another reason for the higher L/B ratio of
ligand 4 compared with 5. The performance of rhodium catalyst
modified by ligands 7 and 8 again confirmed this trend.
H
P
P
P
Rh
Rh
Rh
P
P
P
CO
CO
a
CO
c
b
Scheme 2. Two insertion modes of styrene into Rh-H bond.
wileyonlinelibrary.com/journal/aoc
Copyright © 2013 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2013, 27, 474–478

An efficient catalytic system for the formation of linear aldehyde
a
Table 3. Hydroformylation of styrene derivatives by Rh/ligand 1
ꢀ
ꢁ
b
L
LþB
c
d
ꢁ1 b
TOF (h )
Entry
Substrates
Aldehyde (%)
L/B
; %
Conversion (%)
1
2
3
4-Methylstyrene
4-Methoxystyrene
4-Chlorostyrene
a-Methylstyrene
97.7
96.6
95.7
97.4
81.2/15.9 (83.6)
78.8/16.0 (83.1)
78.8/16.4 (82.8)
90.6/0.4 (99.6)
99.4
98.1
99.5
93.4
994
981
995
47
c
4
a
3
ꢂ
[
Rh] = 1.7 mmol, olefin (1.0 ml), S/C = 10 , L/[Rh] = 5, T = 90 C, t = 1 h, p = 1 MPa, toluene (4.0 ml) as solvent.
b–d
See Table 1.
b
Moles of converted olefin per mole rhodium per hour.
c
3
ꢂ
[
Rh] = 1.7 mmol, olefin (1.0 ml), S/C = 10 , L/[Rh] = 5, T = 90 C, t = 20 h, p = 1 MPa, toluene (4.0 ml) as solvent.
the ratio of 81.6/14.5 obtained by the system with ligand 1.
Clearly, the bidentate ligand 1 was not just a simple sum of the
monodentate ligand 6, and its performance was much superior
to ligand 6. Comparing bidentate ligand 4 with its corresponding
summarized in Table 3. The presence of an electron-donating
or an electron-withdrawing group in position 4 on the phenyl
ring did not affect the reactivity of the aryl alkenes very obviously
(see Table 3, entries 1–3). But a trend that the substrate with
electron-withdrawing groups led to lower L/B than the substrate
with electron-donating groups was observed. Zhang et al. also
revealed this phenomenon when they used ligand (III) in the
monodentate ligand 7,
a positive backbone impact on
regioselectivity was also observed. In addition, the monodentate
ligand 6 showed a higher L/B ratio than monodentate ligand 7
[
9]
(Table 1, entries 6 and 7), likely because the size of the
Rh-catalyzed aryl alkene hydroformylation. It is worth noting
naphthanyl group is larger than that of the phenyl group. To
sum up, in order to obtain high linear aldehyde regioselectivity
in the hydroformylation of styrene, the bidentate phosphite 1
containing the rigid binaphthol skeleton and electron-
withdrawing group is the best choice among the ligands tested.
To better compare the activity and selectivity of these catalysts,
hydroformylation was performed under milder conditions so that
styrene conversion was controlled to be lower than 30%
that the steric hindrance of the substrates remarkably influences
[
9]
the regioselectivity. In our case, when a-methylstyrene was
used as the substrate, few branched aldehydes were yielded
(Table 3, entry 4), but the reaction rate decreased obviously. This
might be explained by steric hindrance inhibiting the formation
of the benzylic Rh species (Scheme 2b), which would tend to pro-
[
25]
duce branched aldehyde.
(see supporting information). The results illustrated a similar
trend for linear aldehyde selectivity as in Table 1, which increased
at higher conversion.
Conclusions
Reaction conditions play an important role in
hydroformylation; thus we set out to find the optimal conditions
within the system of ligand 1/Rh. The representative results of li-
gand/Rh molar ratio and initial pressure and temperature are
shown in Table 2. It can be seen that the ligand/Rh molar ratio
has a dramatic effect on hydroformylation. Molar ratios ranging
from 3.0 to 10.0 were scanned for the optimal value (see Table 2).
A yield of 75.5% of 3-phenylpropanal was obtained at a ligand/Rh
In summary, the influence of the steric and electronic properties
of ligands on activity and regioselectivity was investigated in the
hydroformylation of styrene. The results demonstrated that
the rigid binaphthyl skeleton and electron-withdrawing
dipyrrolylphosphino group were very important in obtaining
high activity and high linear aldehyde selectivity. Thus the 2,
2 -bis(dipyrrolylphosphinooxy)-1,1 -(ꢀ)-binaphthyl ligand (1) can
effectively improve the reaction activity and linear aldehyde
selectivity in the Rh-catalyzed hydroformylation of styrene and
its derivatives. Satisfactory activity and good regioselectivity
to the linear aldehyde were therefore obtained in the
hydroformylation of styrene or its derivatives when (Rh(acac)
0
0
ꢂ
ratio of 5 at 110 C. Further increasing or decreasing the ligand/
Rh molar ratio did not significantly influence the yield of the lin-
ear aldehyde. The product selectivity of styrene hydroformylation
[
24]
strongly depends on the reaction temperature. Thus the tem-
perature impact on the activity and selectivity of ligand 1/Rh
(CO)
2
/ligand 1) was used as catalyst at lower syngas pressure
ꢂ
(
acac)(CO) -catalyzed styrene hydroformylation was investigated
(1 MPa) and relatively moderate temperature (90 C). More
applications of this ligand are under further investigation.
2
ꢂ
in the range 80–120 C, and a good yield of 96.3% aldehydes
was achieved, with an excellent regioselectivity of 85.4% at
ꢂ ꢂ
0 C. Hence the optimum reaction temperature was near 90 C.
9
The total pressure of syngas (CO/H : 1/1) was also a key element Supporting information
2
in the hydroformylation of styrene. As shown in Table 2, pressure
Supporting information may be found in the online version of
this article.
had less impact on catalytic activity and chemoselectivity, but the
enhanced pressure from 1 to 3 MPa greatly decreased the
ꢂ
regioselectivity. The optimal conditions (toluene, 90 C, 1 MPa
Acknowledgment
CO/H , substrate/L/Rh 1000/5/1) through systematic investiga-
2
tions were chosen for the following substrate screening.
We thank the Young Teachers Scientific Research Foundation of
Sichuan University (2011SCU11084) for financial support.
Referring to the results of styrene hydroformylation under op-
timal conditions, it was found that the most active catalyst was a
combination of the rhodium complex and bidentate phosphite li-
gand 1. To evaluate the scope of the reaction, various aryl alkenes
were applied to this catalysis system and the results are
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Appl. Organometal. Chem. 2013, 27, 474–478