HKUST-1/ABNO-catalyzed aerobic oxidation of secondary benzyl alcohols at room temperature

Article abstract of DOI:10.1016/j.tetlet.2018.05.071

Efficient heterogeneous Cu-catalyzed aerobic oxidation of benzyl alcohols was discolsed. The combination of HKUST-1 and ABNO exhibited enhanced catalytic activity compare to the previous HKUST-1/TEMPO system in aerobic oxidation of benzyl alcohols. It was observed that the present catalyst was intrinsically heterogeneous and reusable.

Full text of DOI:10.1016/j.tetlet.2018.05.071

Accepted Manuscript
HKUST-1/ABNO-catalyzed aerobic oxidation of secondary benzyl alcohols at
room temperature
Myeong Jin Kim, Yoo Eil Jung, Chang Yeon Lee, Jinho Kim
PII:
S0040-4039(18)30696-8
https://doi.org/10.1016/j.tetlet.2018.05.071
TETL 50018
DOI:
Reference:
To appear in:
Tetrahedron Letters
Received Date:
Revised Date:
Accepted Date:
17 April 2018
19 May 2018
24 May 2018
Please cite this article as: Kim, M.J., Jung, Y.E., Lee, C.Y., Kim, J., HKUST-1/ABNO-catalyzed aerobic oxidation
of secondary benzyl alcohols at room temperature, Tetrahedron Letters (2018), doi: https://doi.org/10.1016/j.tetlet.
2
018.05.071
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Tetrahedron Letters
HKUST-1/ABNO-catalyzed aerobic oxidation of secondary benzyl alcohols at room
temperature
a
b
b,
a,
Myeong Jin Kim , Yoo Eil Jung , Chang Yeon Lee , Jinho Kim 
a
Department of Chemistry, and Research Institute of Basic Sciences, Incheon National University, 119 Academy-ro, Yeonsu-gu, Incheon 22012, Republic of
Korea
b
Department of Energy and Chemical Engineering, Incheon National University, 119 Academy-ro, Yeonsu-gu, Incheon 22012, Republic of Korea
ARTICLE INFO
ABSTRACT
Article history:
Received
Received in revised form
Accepted
Efficient heterogeneous Cu-catalyzed aerobic oxidation of benzyl alcohols was discolsed. The
combination of HKUST-1 and ABNO exhibited enhanced catalytic activity compare to the
previous HKUST-1/TEMPO system in aerobic oxidation of benzyl alcohols. It was observed
that the present catalyst was intrinsically heterogeneous and reusable.
Available online
2
009 Elsevier Ltd. All rights reserved.
Keywords:
HKUST-1
ABNO
secondary benzyl alcohol
aerobic oxidation
organic synthesis
The selective oxidation of alcohols to aldehydes or ketones is
one of the most important reactions in organic chemistry.
MOFs (metal-organic frameworks), constructing via
coordination bond between inorganic secondary building units
(SBU) and organic building block, have emerged as the
innovative porous materials. Enormous surface areas, versatile
tenability, confined pore-size and regularity of MOFs enable us
1
Traditionally, the oxidation of alcohols has relied on the use of
stoichiometric amounts of oxidants such as chromiun oxides,
manganese oxides, activated DMSO, or Dess-Martin
2
9
periodinane. However, these protocols have suffered from the
to demonstrate the various applications including gas storage,
10
11
12
13
generation of toxic by-products that are undesirable for green
chemistry. On the other hand, aerobic alcohol oxidations using
molecular oxygen as a terminal oxidant have emerged as an eco-
friendly method, because oxygen is easily accessible and
generated water as a sole by-product. For this reason, there has
separation, sensing, drug delivery, electrocatalysis, and
14
catalysis. In particular, catalysis with the MOFs has been
rapidly developing in the past 20 years and becoming the
representative applications for MOFs. Isolated metal site and
periodicity of the MOFs allows spatially separated and well-
dispersed active site. Moreover, inherent their porosity facilitates
the accessibility of active site and the diffusion of substrates and
products through the channel of MOFs. For these reasons, MOFs
has recently gained much attention as a single-site heterogeneous
3
been extensive efforts to develop aerobic oxidation methods.
After Semmelhack reported Cu(I)Cl/TEMPO (2,2,6,6-
tetramethylpiperidine-N-oxyl)
oxidation in 1984, the copper and nitroxyl radical system has
catalyzed
aerobic
alcohol
4
15
played a crucial role in aerobic alcohol oxidation as well as other
catalysts.
5
aerobic oxidative transformations.
Recently, Stahl group
Aerobic alcohol oxidations catalyzed by several MOFs based
system were reported during the past few years. Noble metal and
MOFs composites such as Au@MOF-5, Au@MIL-101 and
disclosed that Cu(I)OTf/bpy (2,2′-bipyridine)/TEMPO/NMI (N-
methylimidazole) catalyst showed improved catalytic reactivity
6
and substrate scope. In addition, they have undertaken various
Pt@DUT-5, have been employed as heterogeneous catalyst for
studies to understand the mechanism of Cu/TEMPO-catalyzed
16
7
aerobic alcohol oxidation.
However, despite their high
aerobic alcohol oxidation. Although fruitful progress has been
efficiency and stable catalytic activity, the high cost and
cumbersome incorporation process for the noble metal limit the
application of these systems. To develop the cost-effective
catalyst, Garcia and coworkers reported the aerobic alcohol
oxidation catalyzed by low-cost Cu-MOFs, HKUST-1
made in homogeneous Cu catalysis for aerobic alcohol oxidation,
heterogeneous Cu-catalyzed aerobic alcohol oxidations are still
8
less investigated.
—
——


Corresponding author. Tel.: +82-32-835-8409; fax: +82-32-835-0797; e-mail: cylee@inu.ac.kr (C. Y. Lee)
Corresponding author. Tel.: +82-32-835-8218; fax: +82-32-835-0762; e-mail: jinho@inu.ac.kr (J. Kim)

2
Tetrahedron
8d
1
(Cu
3
(BTC)
2
,
BTC: 1,3,5-benzenetricarboxylate).
In the
B). We measured H NMR yield of portion A at once (38%) and
1
presence of TEMPO and inorganic base (Na
2
CO ), HKUST-1
3
H NMR yield of portion B after additional 12 h stirring (38%),
catalyzed oxidative conversion of primary alcohols to the
corresponding aldehydes at 75 C. In addition, nanoscaled
and no further oxidation was observed without HKUST-1. In
addition, inductively coupled plasma optical emission
spectrometry (ICP-OES) analysis of the filtrate revealed that 1.15
ppm of the copper existed in the reaction mixture corresponding
to 0.05% of the copper leaching. These results supported that the
present HKUST-1 catalysis is intrinsically heterogeneous though
little Cu leaching, which is catalytically irrelevant, was
o
Cu (BTC) and UiO-66-Sal-CuCl were employed in the aerobic
3
2
2
8f 8g
alcohol oxdiation by Wang and Luan group, respectively.
Although these systems showed good catalytic performance for
the oxidation of primary benzyl alcohols, the oxidations of
secondary benzyl alcohols were sluggish even at high
temperature (A in Scheme 1). Therefore, an efficient aerobic
oxidation of secondary benzyl alcohols to ketones by using the
8d
observed.
1
7
Table 1. Optimization for of HKUST-1/ABNO-catalyzed
cost-effective Cu-MOFs still remains a challenge to overcome.
a
aerobic oxidation of 1-(4-methylphenyl)ethanol.
Entry
HKUST-1
ABNO
(mol %)
10
Base
Solvent
Yield
(%)
66
b
(mol %)
1
2
3
4
5
6
7
8
9
20
Na
Na
Na
Na
2
2
2
2
CO
CO
CO
CO
3
3
3
3
CH
CH
DCE
3
CN
20
20
20
20
20
20
20
10
10
10
10
10
10
10
10
10
10
10
5
2
Cl
2
90
99
81
95
82
99
26
99
98
50
toluene
DCE
DCE
DCE
DCE
DCE
DCE
DCE
NaHCO
CO
CO
pyridine
3
Scheme 1. Cu-MOF-catalyzed aerobic oxidations of benzyl
alcohol oxidation
K
2
3
Cs
2
3
In 2009, Iwabuchi group reported a practical route for the
synthesis of ABNO (9-azabicyclo[3.3.1]nonane N-oxyl), and
revealed that the synthesized ABNO was able to catalyze the
oxidation of secondary alcohols including sterically hindered
Cs
Cs
Cs
2
CO
CO
CO
3
3
3
1
1
0
1
2
18
substrates under Anelli’s Condition.
After Iwabuchi’s
c
5
2
achievement, ABNO has been widely employed as a potent
nitroxyl radical for homogeneous aerobic oxidation of secondary
a
Reaction conditions: 1a (0.5 mmol), HKUST-1, ABNO, and base (1.0
19
b
equiv) in solvent (1.0 mL) under O
determined by
tetrachloroethane). Under air.
2
at room temperature for 15 h. Yield
NMR spectroscopy (internal standard: 1,1,2,2-
alcohols. To the best of our knowledge, however, no report
described the use of ABNO in heterogeneous aerobic oxidation
of secondary alcohols. Herein, we describe HKUST-1/ABNO-
catalyzed aerobic alcohol oxidation which shows better catalytic
activity than the previously reported heterogeneous Cu catalytic
systems including HKUST-1/TEMPO (B in Scheme 1).
1
H
c
The optimized oxidation conditions were then tested with a
number of different secondary benzyl alcohols (Table 2). It
wasobserved that the aerobic oxidation of 1-phenylethanols with
various substituents in para position of phenyl group showed
excellent yields (2a–2g) except 2b and 2h. The use of increased
amounts of ABNO provided an excellent yield of 2b (99%),
however, the moderate yield of 2h was still obtained even in high
loading of ABNO presumably due to the coordination effect of
cyano group to HKUST-1. It was observed that the use of 10
mol % of ABNO gave excellent conversions and product yields
in the synthesis of 2i and 2j. Other ketones such as benzophenone
and 2-acetonaphthone were efficiently synthesized by the present
oxidation of the corresponding alcohols (2k and 2l). While the
production of 1-indanone was successful (2m), the yield of 1-
tetralol was moderate even at high temperature (2n). It is worth
mentioning that the double bond and thiophene did not affected
by the present aerobic oxidation (2o and 2p). The aerobic
With 1-(4-methylphenyl)ethanol 1a as a model substrate, we
investigated the catalytic activity of HKUST-1/ABNO system
under molecular oxygen (Table 1). Gratifyingly, it was observed
that the use of HKUST-1/ABNO facilitated the aerobic oxidation
of 1a to produce 1-(4-methylphenyl)ethanone 2a at room
temperature (entry 1). The use of DCE (dichloroethane) exhibited
an excellent yield among solvents screened, however, the used
HKUST-1 was decomposed and the reaction mixture looked
homogeneous regardless of solvents (entries 2–4). To address
this issue, a variety of bases were examined, and the use of
Cs CO showed superior reactivity without decomposition of
2 3
20
HKUST-1 (entries 5–7). Organic bases such as pyridine showed
poor reactivity (entry 8). The present aerobic oxidation was
efficient even with the reduced amount of HKUST-1 and ABNO
oxidation of diol 1q for the synthesis of benzil, which was widely
used as photoinitiator,
conditions. Two primary benzyl alcohols that showed poor
results in the previously reported HKUST-1/TEMPO system
(
entry 9–10). When the present oxidation was carried out under
air instead of O , the lower yield was observed (entry 11).
Control experiments revealed that HKUST-1, ABNO, and O
22
was moderate in the optimized
2
2
21
were essential for the present aerobic oxidation.
(
less than 10 % yield) were examined under the optimized
8d
To figure out the present oxidation is heterogeneous or
homogeneous, filtration experiments were carried out. We set up
the HKUST-1 catalysis with 1a under optimized conditions.
After 3 h, HKUST-1 was eliminated from reaction mixture by
filtration, and the filtrate was separated into two portions (A and
conditions, and it was observed that HKUST-1/ABNO system
efficiently catalyzed the aerobic oxidation of primary benzyl
alcohols such as 1r and 1s though high loading of ABNO was
required to obtain acceptable yields. However, the oxidation of

aliphatic alcohols such as 1t and 1u still remains a challenge in
the HKUST-1/ABNO system.
The present oxidation of secondary benzyl alcohols was
effective on larger scale. The exposure of 10 mmol of 1a to the
present reaction conditions provided 2a in 92 % yield. With the
used catalyst in the scale up experiment, the reusability of
HKUST-1 was investigated. To separate the used HKUST-1
from the reaction mixture, simple centrifugation and filtration
Table 2. Substrate scope of the aerobic oxidation catalyzed by
a
HKUST-1/ABNO.
3
were performed with CH CN and water, and 62% of the used
HKUST-1 was collected. The recollected HKUST-1 could be
8,23
reused at least three times without the loss of reactivity.
In conclusion, we developed a Cu-MOF-catalyzed aerobic
oxidation of secondary benzyl alcohols for the first time. The use
of HKUST-1 with ABNO efficiently catalyzed the oxidation of
benzyl alcohols with molecular oxygen as an eco-friendly
oxidant at room temperature. The hot filtration experiments and
the analysis of ICP-OES revealed that HKUST-1-catalyzed
aerobic oxidation was intrinsically heterogeneous and the
observed little Cu leaching is catalytically irrelevant. Various
secondary benzyl alcohols as well as primary benzyl alcohols,
which showed poor yields in the previous HKUST-1/TEMPO
system, were efficiently converted into the corresponding ketones
and aldehydes. The developed catalysis was effective in larger
scale. The used HKUST-1 was readily separated by
centrifugation and could be reused at least three times without the
loss of reactivity.
Acknowledgments
This research was supported by Basic Science Research
Program through the National Research Foundation of Korea
(NRF) funded by the Ministry of Science and ICT (NRF-
2018R1A1A1A05019774).
Supplementary Material
Supplementary data (experimental procedures for alcohol
1
13
oxidation, and H and C NMR spectra of the products)
associated with this article can be found, in the online version, at
http://dx.doi.org/10.1016/j.tetlet.
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Graphical Abstract
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HKUST-1/ABNO-catalyzed aerobic
oxidation of secondary benzyl alcohols at
room temperature
a
b
b,
a,
Myeong Jin Kim , Yoo Eil Jung , Chang Yeon Lee , Jinho Kim 
Highlights

3
-
HKUST-1/ABNO-catalyzed aerobic oxidation of
secondary alcohols was achieved.
A variety of benzyl alcohols underwent the
present oxidation efficiently.
The present protocol was intrinsically
heterogeneous and effective on larger scale.
The used HKUST-1 was easily recycled, and
could be reused at least three times.
-
-
-