Hydrogen bond directed aerobic oxidation of amines via photoredox catalysis

Article abstract of DOI:10.1039/c8cc06603e

An application of H-bonding interactions for directing the α-C-H oxidation of amines to amides and amino-ketones catalyzed by an organic photocatalyst is reported. The high efficiency of this method is demonstrated by the aerobic oxidation of pyrrolidines, diarylamines and benzylamines bearing urea groups with high yields and a wide substrate scope.

Full text of DOI:10.1039/c8cc06603e

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Hydrogen Bond Directed Aerobic Oxidation of Amines by
Photoredox Catalysis
Hongyu Wang,†,* Yunquan Man,† Kaiye Wang, Xiuyan Wan, Lili Tong, Na Li and Bo Tang*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
An application of H-bonding interactions for directing the α-C-H controlling nucleophiles as a result of directing the addition
oxidation of amines to amides and amino-ketones catalyzed by an reaction of imines under photoredox conditions (Scheme 1B).
organic photocatalyst is reported. The high efficiency of this Herein, we disclose a strategy involving a urea derived H-bond
method is demonstrated by the aerobic oxidation of pyrrolidines, directed oxidation of amines to amides and amino-ketones
diarylamines and benzylamines bearing urea groups with high (Scheme 1C).
yields and wide substrate scope.
Pyrrolidines are found in numerous natural products and
bioactive molecules; these building blocks are easily accessible
through
a
variety of reported procedures.6 However,
Efficient transformation of organic amines is an important
strategy for the construction of nitrogenous and other
functionalized compounds, such as Mannich-type reaction and
cross-coupling reaction via the cleavage of C-N bond.1 In
particular, photoredox catalysis has emerged as an important
tool for the efficient transformation of organic amines, and
many literatures have been reported on the oxidation of
alkylamines via visible-light-induced processes.2 In general, the
nitrogen-radical-cation will be firstly generated through
photoredox catalysis, and then the imine is obtained after a
proton’s elimination, which will be attacked by a nucleophile
(Scheme 1A). Although this catalytic mode is widely applied in
large number of organic reactions, it still exists some
challenging problems to be resolved at the moment, such as
long reaction time and narrow substrate scope. Therefore,
searching an efficient method for resolving these problems is
highly desirable.
investigations devoted to the transformation of pyrrolidines to
other useful molecules are limited.7 Based on our previous
successes,8 the model reaction was first performed with 1a
and organic photosensitizer
I
(Et(S*/S
= 2.3 V) with visible
)
light irradiation under aerobic conditions. The reaction was
found to proceed well and gave oxidation product 2a in a 73%
yield within 4 h (Table 1, entry 1). Control experiments were
conducted to investigate the influence of various reaction
parameters, as shown in Table 1. When the reactions were
performed in the absence of light, photocatalyst or O2, no
products were yielded. These result illustrated that the
reaction was oxidized by oxygen under visible light irradiation
(entries 2-4). Moreover, 2a was obtained in lower yields
(entries 5 and 6) when the reaction was conducted in the
presence of chloroform or 1,2-dichloroethane as the solvent.
After that, careful screening of the reaction conditions was
continued, but improved reaction outcomes were not
obtained even using other photosensitizers.
The introduction of efficient directing groups is an important
strategy for improving regioselectivities and yields in organic
reactions.3 Meanwhile, H-bonding interaction present a vital
role for the design of directing groups, which can bind
together two different molecules in the transition states.3g, 3h, 3j,
A) The general mode for the oxidation of alkylamine by photoredox catalysis:
R'
R'
R'
R'
N
[O]
hv
N
N
-H
N
Nu
R
R
R
R
Nu
R''
R''
4
R''
R''
Inspired by these observations, we postulated that an amine
B) Our design:
O
O
O
O
protected as a urea may offer a H-bonding interaction for
R''
R''
R''
N
R''
N
N
N
N
N
H
[O]
hv
N
N
R
H
R
R
R
H
H
-H
Nu
R''
R''
Nu
R''
R''
H-bonding interaction
C) This work:
O
O
O
R''
R''
N
N
H
visible light
O2
R''
N
R
N
H
H
R
and
N
N
H
R
R''
O
O
R''
R'' = Aryl, Alkyl
R'' = H
Scheme 1. The generations of N-centered radical species and their applications.
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Table 1. Optimization of reaction conditions.a
desired product was obtained when the reactant derived from
piperidine was exposed to the catalytic system. Subsequently,
the urea with meta- and ortho- substituted bromine were
investigated, and all the reactions proceeded smoothly and
furnished the corresponding products. Moreover, para-
substituted fluorine, chlorine and 3,5-CF3 group were also
investigated despite of moderate yields under the mild
conditions. In addition, the ketonic carbonyl of 2a was easily
reduced by NaBH4 in a 92% yield in a short time, and the
hydrolyzation of 2a to furnish the corresponding amino-ketone
was also realized using aqueous H2SO4 (see Scheme S1). To
expand the applications of this reaction, we continued to
examine the direct oxidation of acyclic amines for preparing
ketones by this strategy (Table 3).9 We first examined
substrates with alkyl groups such as ethyl and Bn, which
successfully furnished the corresponding products in moderate
yields. To our delight, substrates with aryl groups can be
efficiently converted to diarylketones in excellent yields. For
example, diphenylketone 4c was obtained in an 88% yield by
photoredox catalysis. For explaining the importance of the
urea group, the oxidation reaction with diphenylmethanamine
was carefully performed under the standard conditions.
However, benzophenone (4c) was not obtained after stirring
for 12 h, which indicated that the hydrogen bond was essential
for the reaction. Then, the variations of the substrates by fine
tuning the electronic and steric effects were investigated to
expand the applications of this method. Introducing electron-
withdrawing and electron-donating groups showed no
influence on the reaction outcome, and meta- and ortho-
substituted ketones (4d, 4j and 4l) could be obtained in high
yields. In addition, 4m and 4n were furnished in 32% and 61%
yields, respectively. Notably, product 4q could be easily
converted to fenofibrate with 77% yield over two steps.
N-Acyl ureas are important structural motifs present in
numerous bioactive compounds, and, the benzoyl ureas are
often found in agrochemicals and insect growth regulators.
Therefore, the development of novel methods for efficiently
synthesizing these compounds is in high demand.10 Herein, we
proposed that this visible-light-induced method would be a
desirable strategy for preparing benzoyl ureas. We found that
the efficient oxidation of 5a using Mes-AcrClO4 (Et(S*/S ) = 2.06
V) can be achieved in a 80% yield (Table S1). In addition, the
scope of the reaction was carefully explored by introducing
different groups at the para-, meta- and ortho- sites of the
benzene ring. As shown in Table 4, all substrates furnished the
corresponding products in good to excellent yields via
photoredox catalysis. In addition, four commercial insecticides
were synthesized under these mild conditions, and penfluron
could be carried on a gram-scale synthesis with 0.76 g (71%
yield).
aUnless otherwise noted, all the reactions were performed with 1a (0.05 mmol) in
the presence of a catalyst (5 mol%) in solvent (1 mL) for 4 h. Yields of 2a are
isolated yields. NR: no reaction.
Table 2. The scope of the reactions.a
X
X
HN
HN
I (5 mol%), blue LED
acetone, air, 35 o
N
HN
O
n
O
O
C
n
Ar
Ar
n = 1, 2
n = 1, 2
2, yield (%) / time
1
2a, X = H, 73 / 4 h
Br
Br
O
(70 / 6 h)*
2b, X = 4-Me, 55 / 6 h
2c, X = 4-OMe, 81 / 2.5 h
2d, X = 4-CF3, 55 / 7 h
2e, X = 4-F, 79 / 3 h
2f, X = 4-Cl, 86 / 2.5 h
2g, X = 4-Br, 69 / 2 h
(70 / 4 h)*
2h, X = 3-F, 39 / 6 h
2i, X = 3-Cl, 58 / 3 h
2j, X = 3-Me, 50 / 3 h;
CCDC (2j, ref.5): 1833871
2k, X = 2-F, 21 / 6 h
HN
N
H
O
O
2r, X = H, 49 / 1.5 h
(47 / 4 h)*
2s, X = Cl, 38 / 5 h
O
NH
HN
X
X
Cl
O
Br
HN
N
H
O
2t, X = Cl, 62 / 5 h
(60 / 8 h)*
2u, X = F, 30 / 14 h
2l, 32 / 5 h
Ph
O
NH
HN
O
Br
CF3
O
O
2v, 40 / 2 h
2m, X = H, 45 / 3 h
HN
N
H
HN
N
CF3
O
2n, X = 4-F, 51 / 1.5 h
2o, X = 4-Cl, 38 / 1 h
2p, X = 4-Br, 47 / 1 h
2q, X = 3-Me, 48 / 1.5 h
H
O
X
aAll reactions were performed on a 0.05 mmol scale under the optimized
conditions. Yields of 2 are isolated yields. *The reactions were performed on a
0.20 mmol scale under the optimized conditions. φ15 mol % I was used.
Under the optimized conditions, the scope of the reaction
was then investigated by fine tuning the steric effects and
electronic influences of the substituents (Table 2). Para-
substituents on the benzene rings were well tolerated in the
reactions regardless of their electron-withdrawing or electron-
donating effects. Meanwhile, substrates with meta- or ortho-
substituents, such as fluorine, chlorine and methyl, were
examined in this reaction and afforded the corresponding
products in moderate yields. In addition, a 32% yield of the
To elucidate the mechanism of the reaction, we carried out
control experiments (Scheme 2). First, the influences of urea in
the optimized reaction were determined by changing the
substituents on the pyrrolidines (Scheme 2a). No desired
product was obtained by this method if no protecting group
was
2 | J. Name., 2012, 00, 1-3
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Table 3. Substrate scope for the oxidation of benzylamines by photoredox catalysis.a
reaction. Furthermore, if TEMPO was added into the system,
no reaction was observed despite increasing the reaction time.
To illustrate the importance of this method, conventional
approaches for the oxidation amines using DDQ and TBHP
were subsequently examined,11 but no products were
furnished under these conditions. In addition, the Stern-
Volmer quenching experiments were also carried out to get
further information on the reaction mechanism. As shown in
Scheme 2b, the excited state of the photocatalyst
I was
efficiently quenched by 1a. According to these results and
previous works,12 a plausible pathway was proposed (Scheme
2c). First, amine
excited photoredox catalyst under visible light, and then a
proton is abstracted by the O2 to generate intermediate
A is oxidized to an intermediate B by the
C
.
-
After the addition reaction between
C
and HO2 assisted by H-
is generated, which
binding interaction, the addition product
D
is then converted to the product after removal of H2O.
OMe
a
OMe
I (5 mol%), blue LED
R
N
acetone, air, 35 o
C
R
H
O
N
2
1
Photoredox catalysis for this reaction:
1aa, R = H:
standard conditions, complex mixture
1bb, R = p-BrC6H4CO:
standard conditions, 40% yield, 4 h
1cc, R = p-BrC6H4NMeCO:
standard conditions, 39% yield, 6 h
1a, R = p-BrC6H4NHCO:
aAll reactions were performed on a 0.05 mmol scale under the optimized
conditions. *The reactions were performed on a 0.30 mmol scale under the
optimized conditions. Yields of 4 are isolated yields. (b) BBr3, THF, H2O; (c)
isopropyl 2-bromo-2-methylpropanoate, KHCO3, isopropanol, reflux.
standard conditions, 81% yield, 4 h
added 1.5 equiv. TEMPO: NR, 4 h
Table 4. Substrate scope for the oxidation of benzylamines by photoredox catalysis.a
Conventional approaches instead of this method:
with DDQ, NR
with TBHP and CuBr in toluene, 100 oC, complex mixture
with TBHP and FeCl3 in toluene, 100 oC, complex mixture
b
O
c
Ar
N
N
R
H
O2
O
R'
O
C
H
SET
PC
O2
PC
hv
O
O
Ar
Ar
PC*
N
N
N
N
SET
H
R
R
H
H
R'
O
R'
aAll reactions were performed on a 0.05 mmol scale under the optimized
conditions. *The reactions were performed on a 0.20 mmol scale under the
optimized conditions. Yields of 6 are isolated yields.
O
D
B
Ar
O
N
N
O
R
H
H
O
O
Ar
R'
N
N
H
Ar
A
H
R
N
N
H
-H2O
+
R
O
used (1aa). Meanwhile, when the urea group was replaced
with p-BrC6H4CO (1bb), the desired product was obtained in
only a 40% yield. If the acidic N-H bond of urea was protected
with methyl group (1cc), only 39% yield was obtained.
Therefore, H-binding interactions play an important role in this
R'
R' = Aryl, Alkyl
R' = H
Scheme 2. Mechanistic research. (a) Control experiments; (b) Catalyst quenching
experiment; (c) The possible reaction pathway. DDQ: 2,3-dicyano-5,6-
dichlorobenzoquinone; TBHP: tert-Butyl hydroperoxide.
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3
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In summary, we have developed a hydrogen-bond directed
aerobic oxidation reactions by photoredox catalysis and
successfully applied this method to the transformation of C-N
bonds. Moreover, pyrrolidines-derived substrates and
benzylamines bearing urea groups could be efficiently oxidized
under aerobic conditions to furnish the corresponding ketones
and benzoyl ureas in excellent yields. The excellent yields and
broad substrate scope illustrated the efficiency of this strategy
for achieving novel reactions by photoredox catalysis.
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Financial support from the National Natural Science
Foundation of China (21535004, 91753111, 21874086,
21602125 and 21390411), the Key Research and Development
Program of Shandong Province (2018YFJH0502), Natural
Science Foundation of Shandong Province (ZR2016BQ38),
Project of Shandong Province Higher Educational Science and
Technology Program (J16LC14) and China Postdoctoral Science
Foundation (40411585) is gratefully acknowledged.
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712-717; (k) H. J. Davis, M. T. Mihai, R. J. Phipps, J. Am. Chem.
Soc. 2016, 138, 12759-12762; (l) L. Ping, D. S. Chung, J.
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Chem. 2012,
CCDC 1833871
4
, 603-614.
2j
(
)
contains the supplementary
Conflicts of interest
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Hydrogen Bond Directed Aerobic Oxidation of Amines by
Photoredox Catalysis
³
Hongyu Wang,³,* Yunquan Man, Kaiye Wang, Xiuyan Wan, Lili Tong, Na Li and Bo Tang*
An application of H-bonding interactions for directing the Þ-C-H oxidation of amines to
amides and amino-ketones catalyzed by an organic photocatalyst with high yields and
wide substrate scope is reported.