The dehydrogenative oxidation of aryl methanols using an oxygen bridged [Cu-O-Se] bimetallic catalyst

Article abstract of DOI:10.1039/d1nj00712b

Herein, we report a new protocol for the dehydrogenative oxidation of aryl methanols using the cheap and commercially available catalyst CuSeO₃·2H₂O. Oxygen-bridged [Cu-O-Se] bimetallic catalysts are not only less expensive than other catalysts used for the dehydrogenative oxidation of aryl alcohols, but they are also effective under mild conditions and at low concentrations. The title reaction proceeds with a variety of aromatic and heteroaromatic methanol examples, obtaining the corresponding carbonyls in high yields. This is the first example using an oxygen-bridged copper-based bimetallic catalyst [Cu-O-Se] for dehydrogenative benzylic oxidation. Computational DFT studies reveal simultaneous H-transfer and Cu-O bond breaking, with a transition-state barrier height of 29.3 kcal mol^?1

Full text of DOI:10.1039/d1nj00712b

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The dehydrogenative oxidation of aryl methanols
using an oxygen bridged [Cu–O–Se] bimetallic
catalyst†
Cite this: New J. Chem., 2021,
5, 5775
4
Received 11th February 2021,
Accepted 11th March 2021
a
a
a
Prabhupada Choudhury, Pradyota Kumar Behera, Tanmayee Bisoyi,
a
ac
a
Santosh Kumar Sahu, Rashmi Ranjan Sahu, Smruti Ranjita Prusty,
Abigail Stitgen, Joseph Scanlon, Manoranjan Kar and Laxmidhar Rout
DOI: 10.1039/d1nj00712b
b
b
c
ad
*
rsc.li/njc
9
Herein, we report a new protocol for the dehydrogenative oxidation of such as TEMPO, AZADO, ABNO, and NMI. Over the decades,
aryl methanols using the cheap and commercially available catalyst major advances have been made in the development of catalytic
CuSeO
only less expensive than other catalysts used for the dehydrogena- transition metals.
tive oxidation of aryl alcohols, but they are also effective under mild Among the transition metals used, copper is very cheap and
conditions and at low concentrations. The title reaction proceeds a suitable choice of metal for alcohol oxidation in the presence
3
ꢀ2H
2
O. Oxygen-bridged [Cu–O–Se] bimetallic catalysts are not methods for the aerobic oxidation of alcohols using different
7
–11
1
2–14
with a variety of aromatic and heteroaromatic methanol examples, of nitroxyl radicals, organic peroxide, and molecular oxygen.
obtaining the corresponding carbonyls in high yields. This is the first Mark ´o et al. have demonstrated a Cu(I)-phen-(DABDH ) system
2
1
3
example using an oxygen-bridged copper-based bimetallic catalyst for alcohol oxidation with O in toluene, whereas Sthal et al.
2
[
Cu–O–Se] for dehydrogenative benzylic oxidation. Computational have established a Cu/TEMPO-based catalyst for the aerobic
14
DFT studies reveal simultaneous H-transfer and Cu–O bond breaking, oxidation of alcohols using ambient air as an oxidant. In addition
with a transition-state barrier height of 29.3 kcal mol
ꢁ
1
15
.
to Cu-based catalysts for alcohol oxidation, SeO
2
is historically
1
6
well-known for allylic oxidation via the Se(IV)–Se(II) cycle. For
The selective and controlled oxidation of organic compounds to example, Sharpless et al. were able to convert cyclohexene to
generate new functional groups and modify existing functional cyclohex-2-enol in 20% yield with 39% of the side-product
1
,2
17
groups in molecules is a significant area in organic synthesis.
Hence, oxidation reactions are at the heart of many important
cyclohexyl t-butyl ether.
It is evident that both selenium and copper are very good
3
transformations pertaining to chemical synthesis. Reactions oxidizers. We considered the effects on alcohol oxidation if
are widely undertaken in the chemical industry using organic both the metal (Cu) and metalloid (Se) are joined through an
4
2
peroxide (ROOH) and molecular oxygen (O ) as terminal oxidants.
oxygen bridge [Cu–O–Se] (Fig. 1). Being inspired in our continuous
Traditional homogeneous methods use Cr/Mn/Os/V metals as effort to explore oxygen-bridged [M–O–M] bimetallic catalyst for
18
stoichiometric oxidants with defined ligands and at high tem- organic reactions, we investigated the oxidation of 1-(furan-2-yl)
perature; this in turn can produce undesirable side products and
5
waste, thus increasing purification costs and pollution. Hence,
clean technology is much appreciated by industry in view of
6
,7
E-factor considerations. Transition metal catalysts capable of
8
2
using molecular oxygen (O ) as a stoichiometric oxidant are
appealing for alcohol oxidation, but only a handful of reports is
available detailing the presence of activator nitroxyl radicals
a
Department of Chemistry, Berhampur University, Odisha-760007, India.
E-mail: ldr.chem@buodisha.edu.in, routlaxmi@gmail.com
b
Department of Chemistry, Ripon College, Wisconsin, WI-54971, USA
c
Department of Physics, IIT Patna, India
d
Adjunct Faculty, School of Chemical Science, Indian Institute of Science Education
and Research, Berhampur, Odisha-760007, India
†
Electronic supplementary information (ESI) available. See DOI: 10.1039/
Fig. 1 Designing a [Cu–O–Se] oxo-bridged bimetallic catalyst for alcohol
d1nj00712b
oxidation.
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Table
1
Results for the oxidation of 1-(furan-2-yl)ethanol under
different conditions
Scheme 1 The oxidation of secondary heteroaromatic ethanols, with reac-
a,b
a
tion times (h) and yields (%).
Alcohol (1 mmol), CuSeO
3
ꢀ2H
2
O catalyst
(
5 mol%, 11 mg), and KOH (1.5 equiv.) were refluxed in 2 ml of toluene.
b
Isolated yield.
ab
Entry
Catalyst
Base
Solvent
Yield (%)
1
2
3
4
5
6
7
8
9
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
CuSeO
3
3
3
3
3
3
3
3
3
3
3
3
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
ꢀ2H
2
2
2
2
2
2
2
2
2
2
2
2
O
O
O
O
O
O
O
O
O
O
O
O
NaOH
KOH
KOH
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
CH CN
3
Dioxane
DMF
t-BuOH
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
20
91/95
30
f
1-(pyridin-4-yl)ethanol (2a–5a, respectively) were oxidized to the
corresponding ketones (2b–5b) in 75–85% yields within 24–30 h.
The highest yield was obtained for 1-(furan-2-yl)ethanol among
the secondary heteroaryl alcohols (Scheme 1).
We next investigated the reactivities of ortho-, para-, and
meta-substituted aryl secondary alcohols (6–16a) under optimal
conditions. 1-(Phenyl)-ethanol (6a) underwent oxidation to
1-(phenyl)-ethanone (6b) in 82% yield (Scheme 2). Among the
p-substituted halogenated aryl alcohols, the reactivity follows the
order F 4 Cl 4 Br 4 I, with 70–88% yields (Scheme 2, 7b–10b).
Electron-donating 1-(4-methoxy phenyl)ethanol and 1-(4-methyl
phenyl)ethanol let to 93% and 87% yields, respectively, (Scheme 2,
11b–12b).
c
KOt-Bu
70
20
30
45
40
80
60
55
40
10
10
0
Na CO
2 3
K
2
CO
3
Pyridine
KOAc
KOH
KOH
KOH
KOH
KOH
KOH
KOH
KOH
KOH
—
10
11
12
13
14
15
16
17
18
CuSO
CuCl
SeO
4
ꢀ2H
2
O
2
ꢀ2H
2
O
2
CuO
—
10
d
0
0
e
CuSeO
3
ꢀ2H
2
O
Similarly, the ortho-substituted secondary aryl alcohols 1-(2-
fluoro phenyl)ethanol and 1-(2-methoxy phenyl)ethanol were
oxidized to the corresponding ketones 13b and 14b in 87–88%
yields (Scheme 2). It is noteworthy that 1-(2-bromo phenyl)ethanol
did not result in any product, which can be attributed to steric
a
Alcohol (1 mmol), catalyst (5 mol%, 11 mg), and base (1.5 equiv.) were
b
c
refluxed in a 25 ml flask in 2 ml of solvent for 28 h. Isolated yield. 80 1C.
d
e
f
No catalyst. No base. Crude NMR yield using an internal standard.
ethanol with the readily and commercially available CuSeO ꢀ2H O effects at the ortho-position. The meta-substituted aryl ethanols
3
2
catalyst (purchased from Sigma-Aldrich). To our delight, 30% of (3-nitrophenyl)ethanol and 1-(3-aminophenyl)ethanol underwent
the desired product 1-(furan-2-yl) ethanone (1b) (Table 1) was oxidation with 88% and 82% yields, respectively (Scheme 2, 15b
formed upon employing 5 mol% catalyst with 1 equiv. KOH in and 16b).
toluene solvent at 80 1C after 20 h. Moreover, we did not observe
Diphenylmethanol and 1-(2-naphthyl)ethanol were oxidized
0
any allylic oxidation to 1-(furan-2-yl)-2-oxoacetaldehyde (1b ), even to benzophenone and 1-(2-naphathyl)ethanone in 91–93% yields
though selenium(IV) is present. A further examination of the (Scheme 3, 17b–18b). Disubstituted 1-(2,4-dichlorophenyl)ethanol
reaction conditions (see the ESI†) revealed that the highest yield and 1-(3,4-dimethoxy phenyl)ethanol resulted in 86–90% yields of
of 1b obtained was 91% after 28 h, with 5 mol% catalyst and the the desired oxidized products (Scheme 3, 19b–20b). The product
19
use of 1.5 equiv. KOH under reflux conditions in toluene solvent.
The preliminary results indicated that bimetallic CuSeO O is of diphenyl methanol after 40 h).
ꢀ2H
capable of promoting alcohol oxidation without the use of
peroxide/nitroxyl radicals/O
Other bases such as Na
17b was isolated with a TON of 510 (1 mol% catalyst and 20 mmol
6
3
2
Further, we investigated the oxidation of primary benzylic
alcohols under the optimal conditions (Scheme 4). Benzyl-,
2
.
2
CO
3
, K
2
CO
3
, KOAc, and pyridine 4-methyl benzyl-, and 4-methoxy benzyl-alcohol underwent oxida-
provided 20–40% yields, whereas only the base KOtBu provided tion to the corresponding ketones 21b–23b in 85–93% yields
0% yield of the desired product (Table 1, entries 4–8). Among (Scheme 4). para-Halobenzyl alcohols were oxidised to the
the solvents screened, t-BuOH, 1,4-dioxane, and DMF afforded
0–60% yields, whereas the solvent CH CN was very effective,
providing 80% yield under these conditions (Table 1, entries
7
4
3
9
2
–12). Under optimal conditions, catalysts other than CuSeO
3
ꢀ
H
2
O, such as CuSO O, CuCl ꢀ2H O, CuO, and SeO , barely
4
ꢀ2H
2
2
2
2
provided the desired product under the same conditions
Table 1, entries 13–16). It is noteworthy that blank reactions
(
without the catalyst CuSeO ꢀ2H O or base KOH did not afford
3
2
any product (Table 1, entries 17 and 18). With the optimized
conditions in hand, we subsequently examined the generality
of the method using a range of heteroaryl secondary alcohols
Scheme 2 The oxidation of o-, m-, and p-substituted secondary benzylic
a,b
a
alcohols, with reaction times (h) and yields (%).
Alcohol (1 mmol),
(
Scheme 1). For example, 1-(furan-2-yl)ethanol, 1-(thiophene-2-
CuSeO O catalyst (5 mol%, 11 mg), and KOH (1.5 equiv.) were refluxed
3
ꢀ2H
2
b
yl)ethanol, 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, and in 2 ml of toluene. Isolated yield.
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products 30–33b in 73–76% yields without any side products
using THF and toluene solvents in a 1 : 1 ratio.
A plausible mechanism
Scheme 3 The oxidation of some secondary aryl alcohols, with reaction
a,b
a
Furthermore, we investigated the mechanism of the CuSeO ꢀ
3
times (h) and yields (%).
Alcohol (1 mmol), CuSeO
3
ꢀ2H
2
O catalyst
2
H O-catalyzed oxidation reaction (Scheme 6). From Table 1
(5 mol%, 11 mg), and KOH (1.5 equiv.) were refluxed in 2 ml of toluene.
2
b
Isolated yield. * TON for 17b is 28 (0.3 mol% cat. and 12 mmol of and Schemes 1–5, it is evident that the catalyst is very good at
diphenylmethanol).
benzylic alcohol oxidations but poor at oxidising aliphatic
alcohols. Se(VI) is most abundant at pH 8, whereas Se(IV) will
be more available in the presence of KOH (pH = 12). In basic
solution, the Se(IV)/Se(0)/Se(II) reduction potentials are very low
6
+
4+
4+
0
0
2ꢁ
20
(
Se /Se = 0.03 V, Se /Se = ꢁ0.30 V, and Se /Se = ꢁ0.67 V).
In that case, copper (E
centre.
to play an important role along with selenium for the dehydration
of aryl methanols.
DFT calculations suggest that the alcohol forms
precursor complex (b) with the CuSeO catalyst (a) with DG =
= 0.33 V) will act as the oxidizing
red
15,21
Hence, in the case of CuSeO ꢀ2H O, copper is believed
3
2
2
2–24
a
Scheme 4 The oxidation of primary aryl methanols, with the reaction
a,b a
3
times (h) and yields (%).
Aryl methanol (1 mmol), catalyst (5 mol%), and
ꢁ1
b
ꢁ14.2 kcal mol . There is simultaneous hydrogen transfer and
base (1.5 equiv.) were refluxed in 2 ml of toluene. Isolated yield.
Cu–O bond breaking in the transition state with a barrier
ꢁ
1
height of 29.3 kcal mol from b to c. Complex c may adopt
structure d with a broken Cu–O bond, with a difference of
0.7 kcal mol in the Gibbs free energies (Fig. 2). Subsequently,
corresponding aldehydes in 80–83% yields (24b–25b). 4-
Nitrobenzyl alcohol underwent oxidation to 4-nitrobenzyl aldehyde
with 80% yield under optimal conditions. 2-Chloro- and 2-fluoro-
benzyl alcohols afforded 80–82% yields, whereas heteroaryl 2-
furfuryl alcohol underwent oxidation to 2-furylethanone (29b) in
ꢁ
1
ꢁ
it forms complex e through precursor d. The catalyst is regener-
ated after the elimination of the oxidised product from the
21
successor complex e/f. Catalyst selectivity for aryl methanols in
90% yield (Scheme 4). It is noteworthy that oxidation stops at the
aldehyde stage without further oxidation to acids. Primary aryl
methanols react faster than secondary aryl methanols in the first
4
h, and then the reaction proceeds smoothly until the end.
Under these conditions, the catalyst CuSeO O is not
3
ꢀ2H
2
able to oxidise aliphatic secondary and primary alcohols. For
example, 1-hexanol, 1-octanol, cyclohexanol, and cyclopentanol
did not undergo oxidation and the starting materials could be
recovered. Finally, the CuSeO
3
ꢀ2H
2
O catalyst is employed for
the oxidation of synthetically important molecules with cotar-
nine skeletons, such as the 2-(4-methoxy-6-methyl-5,6,7,8-
tetrahydro-[1,3]dioxolo[4,5]-isoquinolin-5-yl)-1-arylethanols 30–33a,
which have a broad range of anti-cancer and antitussive proper-
1
9
ties (Scheme 5). It is noteworthy that the oxidation reactions
proceeded smoothly, affording the corresponding carbonyl
Scheme 6 A plausible mechanism for the oxidation of aryl methanols.
Fig. 2 TSs of simultaneous H-transfer and Cu–O bond breaking with a
ꢁ1
difference of ꢁ0.7 kcal mol in Gibbs free energy. Relative G values
a,b
a
ꢁ1
Scheme 5 The oxidation of antitussive cotarnine skeletons.
methanol (1 mmol), CuSeO O catalyst (5 mol%, 11 mg), and KOH
ꢀ2H
1.5 equiv.) were refluxed in 2 ml of solvent (1 : 1, THF : toluene). Isolated
yield.
Aryl
(kcal mol ) are calculated using M06L/6-31G(d)/auto-geometry optimi-
3
2
zation, followed by M06-2x/6-311+G(2d,p)/SDD single-point calculations
including SMD/toluene. Orange = Se; gold = Cu; red = O; black = C; and
white = H.
b
(
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comparison to aliphatic alcohols is anticipated to arise due to
stabilization via Cu–p interactions.
4 G. W. Parshall and S. D. Ittel, Homogeneous Catalysis: The
Application of Catalysis by Soluble Transition Metal Complexes,
Wiley, New York, 2nd edn, 1992, p. 360.
5
6
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In conclusion, we report here a new and relatively inexpensive
7
8
(a) D. Wang, A. B. Weinstein, P. B. White and S. S. Stahl,
Chem. Rev., 2018, 118, 2636–2679; (b) D. S. Mannel,
S. S. Stahl and T. W. Root, Org. Process Res. Dev., 2014, 18,
oxygen-bridged bimetallic CuSeO
3
ꢀ2H
2
O catalyst with [Cu–O–
Se]-type bonds for the first time for the oxidation of aryl methanols
to carbonyl compounds. The catalyst is able to oxidize a diverse
array of primary, secondary, aromatic, and hetero-aromatic aryl
methanols to the corresponding carbonyl compounds without
over-oxidation to the corresponding acids. The reaction does not
need any additives. It is anticipated that the oxygen-bridged
1
503–1508; (c) T. Suzuki, Chem. Rev., 2011, 111, 1825–1845.
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25
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Conflicts of interest
There are no conflicts to declare.
2
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Odisha for research facilities. Dr Rout thanks P. Behera for
recording NMR spectra. SERB/EMR/2016/006898, DST, India;
S & T Department Govt. of Odisha/27562800512107/20/1919;
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