MOF-253-Pd(OAc)2: A recyclable MOF for transition-metal catalysis in water

Article abstract of DOI:10.1039/c6ra12746k

We report palladium(ii)-functionalized MOF-253 (MOF-253-Pd(OAc)₂) as a recyclable catalyst to form all-carbon quaternary centers via conjugate additions of arylboronic acids to β,β-disubstituted enones in aqueous media. We demonstrate MOF-253-Pd(OAc)₂ can be reused 8 times to form ketone products in yields above 75% while maintaining its crystallinity. Additions of a range of stereoelectronically diverse arylboronic acids to a variety of β,β-disubstituted enones catalyzed by MOF-253-Pd(OAc)₂ occur in modest-to-high yields (34-95%).

Full text of DOI:10.1039/c6ra12746k

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MOF-253-Pd(OAc)2: A Recyclable MOF for Transition-Metal
Catalysis in Water
Ryan Van Zeeland,a,† Xinle Li, a,b,† Wenyu Huanga,b,* and Levi M. Stanleya,*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
We report palladium(II)-functionalized MOF-253 (MOF-253- been shown to be capable of supporting a variety of transition-
Pd(OAc)2) as a recyclable catalyst to form all-carbon quaternary metal complexes. The utility of these transition metal-
centers via conjugate additions of arylboronic acids to
β
,β
-
functionalized bpy-MOFs as recyclable catalysts has been
disubstituted enones in aqueous media. We demonstrate MOF- demonstrated in a wide variety of organic transformations
253-Pd(OAc)2 can be reused 8 times to form ketone products in including: cross-coupling reactions;8 reductions of carbon
12
yields above 75% while maintaining its crystallinity. Additions of a dioxide9 and alkenes;10 oxidations of alcohols,11 water,9b,
range of stereoelectronically diverse arylboronic acids to a variety arylboronic acids,13 and alkenes;14 oxidative coupling of
15
of β,β
-disubstituted enones catalyzed by MOF-253-Pd(OAc)2 occur amines;9b C-H borylation and silylation of arenes;10,
in modest-to-high yields (34-95%).
hydrosilylation of ketones;15a and hydroborations10 of alkenes,
aldehydes and ketones.16 These transformations are typically
carried out in aprotic reaction media and the structures of the
bpy-MOFs are known to be relatively stable even at high
temperatures. Much less is understood about the structural
stability of bpy-MOFs and metalated derivatives in polar,
protic solvents, especially at elevated reaction temperatures.17
As a result, metal-functionalized bpy-MOFs as catalysts of
reactions run in polar, protic solvents remain underexplored.
The ability to carry out chemical reactions in the most
efficient, economical, and environmentally responsible
manner is critical to a sustainable chemical enterprise.1 To this
end, synthetic chemists have sought to develop processes that
minimize hazardous reagents while increasing atom economy
and energy efficiency.2 In many reactions, organic solvents
constitute the majority of the chemical matter and are the
primary source of hazardous waste.3 As a result, studies to
replace hazardous organic solvents with more environmentally
benign aqueous media have become a priority.4
Homogeneous transition-metal catalysts with outstanding
activity and selectivity have been developed as a means to
improve atom economy and energy efficiency in a broad range
of reactions.5 Unlike classical heterogeneous catalysts, which
often lack the activity and selectivity of their homogeneous
counterparts, homogeneous transition-metal catalysts are
often difficult or impossible to recover and reuse.6 Metal-
organic frameworks (MOFs) have emerged as a promising
platform for catalysis at the interface of traditional
homogeneous and heterogeneous catalysis.7 In recent years,
MOFs containing 2,2´-bipyridyl linker units (bpy-MOFs) have
Scheme 1 Formation of All-Carbon Quaternary Centres via Conjugate Addition in
Aqueous Media Catalysed by Pd(II)-Functionalized bpy-MOFs
We recently reported palladium(II) complexes of 2,2
bipyridine that catalyse conjugate additions of arylboronic
acids to
-disubstituted enones in aqueous media.18
′-
β,β
However, the palladium species formed upon completion of
the reaction cannot be reused as the catalyst. The ability of
MOFs to support active metal complexes and prevent
bimolecular deactivation processes9b,
12, 19
prompted us to
study palladium(II)-functionalized bpy-MOFs as potentially
recyclable catalysts for these conjugate addition reactions and
a platform for green catalysis in water. Herein, we report
studies to develop palladium(II)-functionalized bpy-MOFs as
recyclable catalysts to form all-carbon quaternary centres via
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conjugate additions of arylboronic acids to
enones in aqueous media (Scheme 1).
β
,β
-disubstituted phenylboronic acid run in the presence of bpy-UiO-67 with no
palladium and an analogous MOF without bipyridine sites,
MOF-253 and bpy-UiO-67, two prototypical MOFs UiO-67-Pd(OAc)2, did not occur to form the conjugate addition
containing 2,2´-bipyridyl linkers, were synthesized via reported product 2a (entries 9 and 10). These results are consistent
protocols from [2,2′-bipyridine]-5,5′-dicarboxylic acid and with supported Pd(II)-bipyridine complexes as the active
either ZrCl4 or AlCl3·6H2O.20 Powder X-ray diffraction (PXRD) catalysts when MOFs C1 and C2 are used to promote the
patterns and nitrogen physisorption analyses of the bpy-MOFs model reaction.
are consistent with reported data (Figures S1-S4). The
The palladium-functionalized MOFs bpy-UiO-67-Pd(OAc)2
postsynthetic metalation of bpy-UiO-67 and MOF-253 was C1 and MOF-253-Pd(OAc)2 C2 perform similarly as catalysts in
performed by treating the bpy-MOFs with Pd(OAc)2 in acetone the model reaction. Two features of MOF-253-Pd(OAc)2 C2 led
at ambient temperature to afford bpy-UiO-67-Pd(OAc)2
(
C1
)
us to select this material for additional catalytic studies. The
and MOF-253-Pd(OAc)2
(
C2) (Figure 1). The integrity of the larger pore size of MOF-25321 compared to bpy-UiO-6722 is
bpy-MOFs was maintained after metalation based on PXRD attractive because the resulting larger pore volumes will be
patterns (Figure S1 and S2). The palladium content of the able to accommodate a wider array of enone and arylboronic
catalysts was determined quantitatively by inductively coupled acid substrates and will facilitate flux of reagents and products
plasma-mass spectrometry (ICP-MS).
into and out of the pores. In addition, we found that MOF-253
could be consistently metalated with approximately 8 weight
% Pd, while we observed significant batch-to-batch variations
for metalation of bpy-UiO-67 with Pd(OAc)2.
Table 1 Identification of Reaction Conditionsa
Figure 1 Idealized structures of bpy-UiO-67-Pd(OAc)2 (C1) and MOF-253-Pd(OAc)2
(
entry
catalyst
(mol % Pd)
C1 (1.5)
wt. % Pd
in MOFb
5.0
temp
(°C)
60
PhB(OH)2
(equiv)
1.2
yield
(%)c
0
C2). Cyan and pink octahedra represent Zr and Al clusters, respectively, while
brown, red, blue, and gray spheres represent Pd(OAc)2 species, O, N, and C
atoms, respectively; H atoms are omitted for clarity.
1d
2d
3
C1 (1.5)
5.0
80
1.2
2
With bpy-UiO-67-Pd(OAc)2 and MOF-253-Pd(OAc)2 in hand,
we studied the model reaction of phenylboronic acid with 3-
methylcyclohex-2-en-1-one 1a to evaluate the utility of these
Pd(II)-functionalized MOFs as catalysts in polar, protic media
(Table 1). The reaction of enone 1a with 1.2 equivalents of
phenylboronic acid in the presence of bpy-UiO-67-Pd(OAc)2
C1 (1.5)
5.0
80
1.2
20
50
74
90
99
99
0
4
C1 (1.5)
5.0
100
100
100
100
100
100
100
1.2
5
C1 (2.5)
5.0
1.2
6
C1 (2.5)
5.0
2.0
7e
8e
9e
10e
C1 (2.5)
8.1
2.0
C2 (2.5)
8.4
2.0
(C1) (1.5 mol % total palladium based on 1a) did not form
bpy-UiO-67 (0.0)
UiO-67-Pd(OAc)2
(2.4)
0.0
2.0
ketone 2a at 60 °C and formed 2a in 2% yield at 80 °C when
the reactions were run in methanol (entries 1 and 2). Changing
the reaction medium from methanol to 50 mM aqueous
sodium trifluoroacetate (aq. NaTFA, pH = 8.2) led to the
formation of ketone 2a in 20% yield when the reaction was run
at 80 °C (entry 3). Ketone 2a was formed in 50% yield upon
increasing the reaction temperature to 100 °C (entry 4).
2.4
2.0
0
a
Reaction conditions: 1a (0.500 mmol), PhB(OH)2 (0.600-1.00 mmol), MOF
catalyst (0.008-0.013 mmol Pd), reaction medium (0.33 mL), 16 h. b Weight % Pd
loaded in the MOF determined by ICP-MS. c Determined by 1H NMR spectroscopy
d
using dibromomethane as an internal standard. Reaction run in methanol.
e Reaction run for 2 h.
We found that the total loading of palladium in the
reaction, the number of equivalents of phenylboronic acid, and
the weight percentage of palladium present in the MOF
significantly impact the yield of our model reaction (entries 5-
7). Increasing the total palladium content of the reaction from
1.5 mol % to 2.5 mol % and the amount of phenylboronic acid
from 1.2 equivalents to 2.0 equivalents led to the formation of
2a in 90% yield (entry 6). When the weight % Pd loaded in the
MOF was increased from 5.0% to 8.1%, the reaction was
complete after two hours and generated 2a in 99% yield (entry
7). The reaction of phenylboronic acid with 1a catalysed by
MOF-253-Pd(OAc)2 C2 in place of C1 also formed 2a in 99%
To gain insight into the stability of MOF-253-Pd(OAc)2 C2
under our aqueous reaction conditions, we evaluated the
recyclability of C2 in our model addition of phenylboronic acid
to enone 1a (Scheme 2). Consistent with our data in Table 1,
the initial reaction with pristine C2 as catalyst formed ketone
2a in 99% yield in less than two hours. Upon recovery of the
catalyst and exposure to additional enone 1a, phenylboronic
acid, and aqueous NaTFA, the yield of ketone 2a dropped to
92% in run 2 and 76-80% in runs 3 and 4 after 2-2.5 hour
reaction times. The yield of 2a could be increased to 90-99%
for runs 5-9 by extending the reaction times.
yield in two hours (entry 8).
Reactions of 1a with
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catalyst is observed during the initial recycling runs. By the
fourth run, the activity of the catalyst is halved and ketone 2a
is formed in 29% yield compared to 60% in the first run.
However, the activity of the catalyst remains consistent in runs
4-10 and 2a is formed in 23-30% yield after one hour.
The PXRD pattern of MOF-253-Pd(OAc)2 C2 after the 10th
run remained unchanged from that of C2 before catalysis
(Figure S5). More importantly, the used C2 possesses
comparably high surface area relative to freshly prepared C2
(Figure S6). However, the decrease in activity of the catalyst
after two hours (run 2 in Figure 2) is not consistent with the
quantity of palladium lost to leaching over two hours. The
combination of these results suggests additional pathways for
deactivation of the palladium catalyst are operative.
Scheme 2 Recycling of C2 in the addition of PhB(OH)2 to enone 1a. Reaction
conditions: 1a (1.50 mmol, 1.00 equiv), PhB(OH)2 (3.00 mmol, 2.00 equiv), C2
(0.075 mmol, 0.050 equiv) and aqueous 50 mM NaTFA (1.00 mL). a Determined
by 1H NMR spectroscopy using dibromomethane as an internal standard.
The results shown in Scheme 2 clearly demonstrate the
ability to reuse MOF-253-Pd(OAc)2 C2 in conjugate additions of
phenylboronic acid to enone 1a. However, these results also
show that, at minimum, partial degradation of the C2 occurs
over time. To verify that the solid MOF-supported 2,2′-
bipyridine complex of Pd(OAc)2 is the active catalyst in these
reactions, we performed leaching tests to eliminate the
possibility for MOF degradation into an active and
homogeneous palladium species (see Supporting Information).
Exposure of C2 to the reagents and reaction conditions for two
hours and analysis of the palladium content of the aqueous
supernatant showed that 0.6% of the palladium had leached
out of C2. However, the palladium found in the supernatant is
not catalytically competent under our reaction conditions.
Ketone 2a is formed in 1% yield after two hours when the
palladium contained in the supernatant is evaluated as a
catalyst of the model reaction under the optimized reaction
conditions.
70
Yield
Run 1, 60% Run 6, 29%
55
40
25
10
Run 2, 54% Run 7, 24%
Run 3, 44% Run 8, 25%
Run 4, 29% Run 9, 25%
Run 5, 31% Run 10, 23%
Scheme 3 Conjugate Addition of Arylboronic Acids to Enones 1a-c catalysed by
MOF-253-Pd(OAc)2 C2. Reaction conditions: 1a-c (0.500 mmol), arylboronic acid
(1.00 mmol), MOF-253-Pd(OAc)2 C2 (0.013 mmol of Pd), 50 mM aqueous NaTFA
(0.33 mL, pH = 8.2), 100 °C, 2-18 h. Isolated yields are reported after purification
by flash column chromatography.
With a robust palladium-functionalized MOF for catalysis in
water identified, we evaluated the scope of the conjugate
addition reaction. Additions of a variety of arylboronic acids to
a selection of enones 1a-c catalysed by MOF-253-Pd(OAc)2 C2
are summarized in Scheme 3. As demonstrated in our
optimization studies, the addition of phenylboronic acid to 3-
methylcyclohex-2-en-1-one 1a occurs to form ketone 2a in
90% yield. Additions of 4-substituted arylboronic acids
1
4
7
10
Run
Figure 2 Low conversion recycling experiments. Reaction conditions: 1a (1.50 containing electron-donating, electron-withdrawing, and
mmol, 1.00 equiv), PhB(OH)2 (3.00 mmol, 2.00 equiv), C2 (0.075 mmol, 0.050
equiv), and aqueous 50 mM NaTFA (1.0 mL, pH = 8.2), 1 h reaction time. Yields of halogen substituents to enone 1a formed ketones 2b
2a were determined by 1H NMR spectroscopy using dibromomethane as an
internal standard.
-d
in 80-
90%. 3-Substituted arylboronic acids are also suitable
substrates for conjugate additions catalysed by C2. Additions
of 3-methoxy- and 3-chlorophenylboronic acids to enone 1a
generated ketones 2e and 2f in 91% yield. The addition of 2-
methoxyphenylboronic acid to 1a occurred to form ketone 2g
in 34% yield. However, additions of 2-substituted arylboronic
acid lacking a strong electron-donating substituent did not
To develop an understanding of the rate of catalyst
deactivation under our reaction conditions, we conducted an
additional recycling study where C2 was reused and the yield
of the conjugate addition reaction was determined after one-
hour reaction times (Figure 2). As expected from our initial
recycling experiment, a slow decline in the activity of the
form conjugate addition products.
In these cases,
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protodeborylation of the 2-substituted arylboronic acid is the
primary reaction pathway observed.23
2
3
4
5
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MOF-253-Pd(OAc)2 C2 also catalyses conjugate additions of
phenylboronic acid to additional cyclic and acyclic
β,β-
disubstituted enones. The addition of phenylboronic acid to 3-
methylcyclopent-2-en-1-one 1b forms ketone 2h in 95% yield.
The addition of phenylboronic acid to acyclic 4-methylpent-3-
en-2-one 1c generated ketone 2i in 83% yield. However,
additions of phenylboronic acid to 3-arylcyclohex-2-en-1-ones
and 3-methylcyclohept-2-en-1-one occurred in <10% yield in
the presence of MOF-253-Pd(OAc)2 C2. The poor reactivity of
these two enone substrates is consistent with analogous
reactions carried out in aqueous media and catalysed by a
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Pd(OAc)2, as competent catalysts for conjugate additions of
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arylboronic acids to
have also demonstrated that MOF-253-Pd(OAc)2 is a reusable
catalyst system that promotes additions of range of
arylboronic acid to -disubstituted enone reaction partners
to form ketones containing quaternary carbon centres. The
development of MOF-253-Pd(OAc)2 as platform for
β,β-disubstituted enones in water. We
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a
2
β,β
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a
transition-metal catalysis in water sets the stage for new
applications of this and related catalyst systems in the areas of
green catalysis. Studies to improve the catalytic activities and
stabilities of MOF-253-Pd(OAc)2 and additional metalated
derivatives for new catalytic transformations in aqueous
environments are on-going.
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We thank Iowa State University, the Iowa State University
Center for Catalysis, and the Ames Laboratory for supporting
this work. The Ames Laboratory is operated for the U.S.
Department of Energy by Iowa State University under contract
number DE-AC02-07CH11358. We thank Professor Gordon J.
Miller (Iowa State University) for use of PXRD instrumentation
in his group.
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