Rhodium-catalyzed highly regioselective hydroformylation-hydrogenation of 1,2-allenyl-phosphine oxides and -phosphonates

Article abstract of DOI:10.1002/adsc.200800087

The rhodium-catalyzed hydroformylation-hydrogenation of 1,2-allenyl-phosphine oxides and -phosphonates is reported in this paper. The regio-selectivity was well controlled, affording only saturated linear γ-phosphinyl aldehydes under the standard conditio

Full text of DOI:10.1002/adsc.200800087

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DOI: 10.1002/adsc.200800087
Rhodium-Catalyzed Highly Regioselective Hydroformylation-Hy-
drogenation of 1,2-Allenyl-Phosphine Oxides and -Phosphonates
Hao Guoa,b and Shengming Maa,b,*
a
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of
Sciences, 354 Fenglin Road, Shanghai 200032, Peopleꢀs Republic of China
Fax : (+86)-21-6416-7510; e-mail: masm@mail.sioc.ac.cn
Shanghai Key Laboratory of Green Chemistry and Technology, Department of Chemistry, East China Normal University
b
3663 Zhongshan Lu, Shanghai 200062, Peopleꢀs Republic of China
Received: February 11, 2008; Published online: May 9, 2008
Supporting information for this article is available on the WWW under http://asc.wiley-vch.de/home/.
Abstract: The rhodium-catalyzed hydroformylation-
hydrogenation of 1,2-allenyl-phosphine oxides and
-phosphonates is reported in this paper. The regio-
selectivity was well controlled, affording only satu-
rated linear g-phosphinyl aldehydes under the stan-
that exist in alkenes, alkynes, and allenes, in principle,
may all undergo hydroformylation to afford different
aldehydes. The hydroformylation of alkenes and al-
kynes has already been well explored,[3,4] however, the
hydroformylation reaction of allenes still remains un-
developed. Only one experimental study in this field
was carried out by Fell and Beutler in 1976 with very
poor selectivities giving a mixture of mono- and di-
dard
phine)-rhodium
conditions:
(carbonyl)tris(triphenylphos-
hydride [RhH(CO)(PPh3)3]
AHCTREUNG
(3 mol%), triphenylphosphine (PPh3) (10 mol%),
carbon monoxide (CO) (2.4”106 Pa), hydrogen
(H2) (subsequently charged to 4.8”106 Pa), toluene,
1008C, 24 h.
A
droformylation of allene and propyne was investigat-
ed at the B3LYP level of density functional theory by
Jiao et al.[7] Even now, the hydroformylation of al-
lenes still furnishes challenges in controlling the
chemo-, regio-, and stereoselectivities. As shown in
Scheme 1, several different aldehydes such as b,g- or
a,b-unsaturated enals and saturated aldehydes A/B/C
may be formed. On the other hand, allenes have re-
cently been demonstrated to be a class of important
Keywords: aldehydes; allenes; hydroformylation;
hydrogenation; phosphorus; rhodium
The hydroformylation of alkenes, discovered first by chemicals with high reactivities and selectivities.[8,9,10]
Roelen in 1938,[1,2] is a powerful method for the syn- Following our recent report on the semihydrogenation
thesis of aldehydes and has been widely explored and of 1,2-allenyl-phosphonate, 1,2-allenyl-phosphine
has become an extremely important industrial pro- oxide, 1,2-allenyl-sulfone, and 2,3-allenoate,[10f] we
cess.[3,4,5] As we know, the unsaturated C C bonds became interested in the hydroformylation of allenes.
À
Scheme 1. The hydroformylation-hydrogenation of allenes.
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Table 1. The hydroformylation-hydrogenation of 1a under
Here, we report the first example of the Rh-catalyzed,
highly regioselective hydroformylation-hydrogenation
of 1,2-allenyl-phosphine oxides and -phosphonates
yielding only saturated linear g-phosphinyl aldehydes,
which are difficult to prepare by other methods.
different catalysts and reaction parameters.[a]
In the beginning, we chose 1,2-allenyl-phosphine
oxide 1a as the model substrate to study the hydrofor-
mylation reaction. At first, we used Pd
C
Entry [M]
Time NMR Yield of 2a
[h]
[%][b]
NR[d]
1
Pd(Ar-BIAN)(dimethyl
C
2
2
3
4
N
48
48
48
24
24
24
2[e,f]
A
13[f]
75
AHCTREUNG
5RhH(CO)
ACHTREUNG
51[f]
85
6
7
RhH(CO)
RhH(CO)
ACHTREUNG
A
89 (72)[i]
[a]
The reaction was carried out at 1008C using 1a
(0.2 mmol), [Rh] (3 mol%), and PPh3 (10 mol%) in 3 mL
of toluene under CO (2.4”106 Pa) followed by charging
to a final combined pressure of 4.8”106 Pa with H2.
The regioselectivity and yield were determined for the
crude reaction mixture by 300 MHz 1H NMR analysis
using CH2Br2 as the internal standard.
The reaction was carried out at 1008C using 1a
(0.2 mmol) and [Pd] (3 mol%) in 3 mL of toluene under
CO (2.4”106 Pa) followed by charging to a final com-
bined pressure of 4.8”106 Pa with H2.
77% of 1a was recovered.
41% of 1a was recovered.
Other unidentified aldehydes were formed.
[Rh] (1 mol%) and PPh3 (3 mol%) were applied.
[Rh] (5mol%) and PPh 3 (15mol%) were applied.
Isolated yield of 2a.
Scheme 2. Pd(Ar-BIAN)(dimethyl fumarate).
G
[b]
[c]
pointingly, only 77% of the starting material was re-
covered (entry 1, Table 1). Then we used
RuHCl(CO)(PPh3)3 (3 mol%) as the catalyst. After
U
careful analysis, it was observed that a 2% yield of a
new product, the linear hydroformylation-hydrogena-
tion aldehyde 2a, was formed. However, it was
formed together with some other unidentified alde-
hydes (entry 2, Table 1). Further screening indicated
[d]
[e]
[f]
[g]
[h]
[i]
that RhH(CO)(PPh3)3 is a better catalyst for this reac-
U
tion with 3 mol% being the best, affording the linear
saturated aldehyde 2a as the only product in 72% iso-
lated yield (entry 7, Table 1).
hydrogenation of 1,2-allenyl-phosphine oxides and
Then the effect of the pressure of CO and H2 was -phosphonates. Some typical results are shown in
examined (Table 2), suggesting that an initial charging Table 4. Alkyl, cyclopropyl, and phenyl groups could
of CO to a pressure of 2.4”106 Pa followed by charg- be introduced into the a-position of the substrates.
ing to a total pressure of 4.8”106 Pa with H2 was the All the substrates gave the linear saturated aldehydes
best (entry 2, Table 2).
as the only products.
Furthermore, we also examined the solvent effect
Based on these results, a possible mechanism was
for the reaction at 608C (entries 1–8, Table 3). All the proposed (Scheme 3).[11] Dissociation of one PPh3
tested solvents gave 2a as the only product in the ligand from RhH(CO)(PPh3)3 yields the square-
G
NMR yield of 56–84% with toluene being the best planar Rh intermediate 3, which may coordinate with
(entry 8, Table 3). The reaction in the absence of free the electron-rich C=C bond in the allene moiety to
PPh3 afforded 2a in lower yield, which indicates that give complex 4. Subsequent hydrorhodiation afforded
10 mol% of free PPh3 is necessary (entry 9, Table 3). the square-planar allylic rhodium intermediate 5.
Since the yield for the reaction at 1008C was a little Then another molecule of CO coordinates with rhodi-
bit higher than that at 608C (entries 8 and 10, um center forming the trigonal bipyramidal complex
Table 3), 1008C was applied for the following studies. 6. Subsequent migrative-insertion leads to the forma-
Thus, conditions A [RhH(CO)(PPh3)3 (3 mol%), tion of acylrhodium intermediate 7, which may fur-
G
PPh3 (10 mol%), CO (2.4”106 Pa) followed by charg- ther react with H2 via oxidative addition and reduc-
ing to a final combined pressure of 4.8”106 Pa with tive elimination to afford the b,g-unsaturated enal 8.
H2, toluene, and 1008C for 24 h] were applied for the On the other hand, the Rh species 3 could coordinate
Rh-catalyzed highly regioselective hydroformylation- with the b,g-C=C bond in 8[12] and undergo a second
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Rhodium-Catalyzed Highly Regioselective Hydroformylation-Hydrogenation
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Table 2. RhH(CO)
C
Table 4. The hydroformylation-hydrogenation of 1,2-allenyl-
phosphine oxides and -phosphonates under conditions A.[a,b]
Entry Initial pressure Final pressure of Yield of 2a by
Entry
1
Isolated yield of 2 [%]
of CO [Pa]
CO+H2 [Pa]
1H NMR [%][b]
R1
R2
1
2
3
4
1.4”106
2.4”106
5.2”106
2.8”106
4.8”106
10.3”106
4.1”106
4.1”106
70
1
2
3
4
5
6
7
8
9
n-Pr
n-Bu
n-Hex
Cyclopropyl
n-Pr
n-Bu
n-Hex
Cyclopropyl
Ph
Ph (1a)
Ph (1b)
Ph (1c)
Ph (1d)
OEt (1e)
OEt (1f)
OEt (1g)
OEt (1h)
OEt (1i)
72 (2a)
68 (2b)
64 (2c)
61 (2d)
89 (72)[c]
77
67
80
1.4”106
6
52.8”10
5
5
5
5
5
2e4)(
29f)(
2g3)(
20h)(
2i)4 (
[a]
The reaction was carried out at 1008C for 24 h using 1a
(0.2 mmol), RhH(CO)(PPh3)3 (3 mol%), and PPh3 (10
mol%) in 3 mL of toluene under the initial pressure of
CO followed by charging to the final combined pressure
with H2.
The regioselectivity and yield were determined for the
crude reaction mixture by 300 MHz 1H NMR analysis
using CH2Br2 as the internal standard.
AHCTREUNG
[a]
The reaction was carried out at 1008C for 24 h using 1
[b]
[c]
(0.4 mmol), RhH(CO)(PPh3)3 (3 mol%), and PPh3 (10
G
mol%) in 4 mL of toluene under CO (2.4”106 Pa) fol-
lowed by charging to a final combined pressure of 4.8”
106 Pa with H2.
Isolated yield of 2a.
[b]
The regioselectivity was determined for the crude reac-
tion mixture by 300 MHz H NMR analysis.
1
Table 3. RhH(CO)
(PPh3)3-catalyzed hydroformylation-hy-
drogenation of 1a using different solvents.[a]
via oxidative addition[12] followed by reductive elimi-
nation[13] to afford the saturated linear aldehydes 2
and regenerate the catalytic species 3.
In conclusion, we have reported a Rh-catalyzed
highly regioselective hydroformylation-hydrogenation
of 1,2-allenyl-phosphine oxides and -phosphonates,
forming only saturated linear g-phosphinyl aldehydes.
A possible mechanism was proposed. Due to the easy
availability of the starting materials[13,14] and potential
of the products with two functionalities, this reaction
will be useful in organic synthesis. Further studies in
this field including the hydroformylation of other al-
lenes and the synthetic applications of this reaction
are being carried out in our laboratories.
1
Entry
Solvent
Yield of 2a by H NMR [%][b]
1
2
3
4
DMF
DMSO
EtOH
CH3CN
70
THF
Benzene
Toluene
Toluene[d]
Toluene[e]
56
64
67
68
5Dioxane
6
7
8
9
10
77
77
84 (67)[c]
65
89 (72)[c]
Experimental Section
[a]
The reaction was carried out at 608C for 24 h using 1a
Typical Procedure for the Hydroformylation-
Hydrogenation of 1,2-Allenyl-Phosphine Oxides and
-Phosphonates; Synthesis of 4-(Diphenylphosphinyl)-
heptanal (2a)
(0.2 mmol), RhH(CO)(PPh3)3 (3 mol%), and PPh3 (10
C
[b]
The regioselectivity and yield were determined for the
crude reaction mixture by 300 MHz 1H NMR analysis
using CH2Br2 as the internal standard.
Isolated yield of 2a.
No PPh3 was applied.
Reaction temperature: 1008C.
PPh3 (10 mg, 0.038 mmol), RhH(CO)(PPh3)3 (11 mg,
A
0.012 mmol), 1a (113 mg, 0.40 mmol), and 4 mL of anhy-
drous toluene were added sequentially into a reaction vessel
in the open air. Then the mixture was transferred into an au-
toclave containing 20 mL of anhydrous toluene, which was
then charged with CO to a pressure of 6.9”105 Pa for three
times to replace the air completely. Then it was charged
with CO to a pressure of 2.4”106 Pa, which was followed by
[c]
[d]
[e]
hydrorhodiation to form the carbo-rhodium inter-
mediate 9 or 10,[12] which may further react with H2 charging the autoclave to a final pressure of 4.8”106 Pa with
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Hao Guo and Shengming Ma
COMMUNICATIONS
Scheme 3. The proposed mechanism for this reaction (L=PPh3).
H2. The resulting reaction mixture was stirred at 1008C (oil
bath). After 24 h, the reaction was cooled to room tempera-
ture, and the pressure was carefully released in a well-venti-
lated hood. After evaporation of the solvent to dryness, the
China. We thank Mr. Shu Wei of this group for reproducing
the results presented in entries 2, 4 and 9 of Table 4(xtabr4).
G
1
resulting mixture was analyzed by 300 MHz H NMR study
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national Program of National Natural Science Foundation of
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Rhodium-Catalyzed Highly Regioselective Hydroformylation-Hydrogenation
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