Merging visible-light photoredox and copper catalysis in catalytic aerobic oxidation of amines to nitriles

Article abstract of DOI:10.1039/c6ob02510b

Visible-light-initiated homogeneous oxidative synthesis of nitriles from amines was accomplished through a combined use of photoredox and copper catalysis. This transformation was performed at room temperature with O₂ as the oxidant.

Full text of DOI:10.1039/c6ob02510b

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
benzene
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DOI: 10.1039/C6OB02510B
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Merging visible-light photoredox and copper catalysis in catalytic
aerobic oxidation of amines to nitriles
Chuanzhou Taoa,b, Bin Wang , Lei Sun , Zhou Liu , Yadong Zhai , Xiulian Zhang , Jian Wang
a
a
a
a
a
a
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
Absract: Visible-light-initiated homogeneous oxidative synthesis of strategys and improvement of the conditions of established
8
nitriles from amines was accomplished through combined use of organic reactions. It is important to note that this concept can
photoredox and copper catalysis. This transformation was bridge the gap between visible-light photoredox catalysis and
9
10
11
performed at room temperature with O
2
as the oxidant.
transition-metal catalysis such as nickel, palladium, gold,
and copper .
1
2
Nitriles are versatile building blocks in the synthesis of natural
products, pharmaceuticals, agricultural chemicals and dyes.1
Development of new methods for the synthesis of aryl nitriles is
In the photoredox cycle, precedent mechanistic
investigations of reductive quenching suggested that iminium
ions were likely by-products in the reactions using tertiary
of significant interest. From an environmental point of view, O
2
7,13
amines as reductants (Scheme 1).
Inspired by this
is considered as an appealing oxidant for sustainable oxidation
chemistry. Obviously, molecular oxygen as oxidant has
remarkable advantages, including its abundance, low cost, and
mechanism, we hypothesized that if primary amines were
chosen as reductant, nitriles could be formed under photoredox
conditions. Herein, as part of our ongoing efforts to develop
method to synthesize nitriles, we disclose a homogeneous dual-
catalysis combining visible-light photocatalysis and copper
catalysis to accomplish efficient conversion amines into nitriles.
To the best of our knowledge, this work demonstrates the first
example of combined visible-light-induced photoredox catalysis
and transition-metal catalysis in transformation of amines to
nitriles. The catalytic system expands the toolbox for synthesis
of nitriles through aerobic oxidation of amines. Moreover, this
new reaction is not only convenient and environmentally
benign, but also can be conducted under mild reaction
conditions with high conversions.
benign by-products (usually H
2
O). The development of catalytic
2
aerobic oxidation methodologies would be highly desirable.
3
4
For example, our group and others developed copper catalyst
systems to directly convert benzylic alcohols into aryl nitriles,
3 2
where NH was used as the nitrogen source and O as the
oxidant. When referred to amines as starting materials, aerobic
oxidative synthesis of nitriles has been studied using
5
a, 5b
5c
heterogeneous catalysts such as TiO
2
,
Nb
2 5
O ,
5d
5e
5f
5g
Au−Pd/ZrO
2
,
Au/TiO
5h
2
,
RuO
2
·xH
2
O/TiO
2
, red Cu(0)/NH Br
. Recently, Stahl et al. reported an efficient
4
6
and Cu(0)/Al
O
2 3
homogeneous copper catalyst system for aerobic oxidation of
primary amines to the corresponding nitriles. Nitroxyl radical
compound ABNO (9-azabicyclo[3.3.1]nonan-3-one-N-oxyl) and
t
ligand 4,4’- Bu
2
bpy are critical for the transformation.
Visible-light-driven photoredox catalysis has become a
powerful means to promote efficient organic transformations
7
under remarkably mild conditions. The latest progress in this
area shows that merging visible photocatalysis and transition
metal catalysis may enable the development of new synthetic
Scheme 1 Concept of visible-light-induced aerobic oxidation of amine to
nitrile.
a.School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang
Initially, we attempted to perform the reaction by treating
2
22005, P. R. of China. E-mail: taocz@hhit.edu.cn; Fax: +86-518-85895401; Tel:
benzylamine 1a with O
shown in Table 1, with Ru(bpy)
2
as the oxidant at room temperature. As
Cl as catalyst, aerobic oxidation
+
86-518-85895401
b.
Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening,
Lianyungang 222005, P. R. of China
3
2
to benzonitrile 2a was not detected (entry 1). Slightly increased
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
t
yield was observed when catalytic amount of LiOBu was
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6
introduced (entry 2) . We systematically evaluated different
transition metal catalysts in the photocatalytic oxidation of
benzylamine (entries 3-8). It was found that yields of product 2a
could be improved to 20-29% when palladium and cobalt were
used (entries 3-5). However, oxidation yields were low when
nickel and iron were added (entries 6-7). To our great
satisfaction, we observed dramatic improvement when copper
catalyst was used (entry 8).
5
6
Ru(bpy)
Ru(bpy)
Ru(bpy)
3
3
3
Cl
Cl
Cl
2
2
2
·6H
·6H
·6H
2
O
CuCl
2
DMSO
17
View Article Online
DOI: 10.1039/C6OB02510B
2
O
Cu(NO
3
)
2
2
DMSO
DMSO
DMSO
DMSO
DMSO
DMF
42
71
7
2
O
Cu(OAc)
CuBr
CuBr
CuBr
CuBr
CuBr
CuBr
8
-
0
0c
18d
9
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
3
3
3
3
3
Cl
2
2
2
2
2
·6H
·6H
·6H
·6H
·6H
2
O
10
11
12
Cl
Cl
Cl
Cl
2
O
2
O
75
2
O
MeCN
DMSO
5
e
82 , 73f
13
2
O
Table 1. Cooperative interactions of photocatalyst with transition metal
catalysts in oxidation amines to nitriles a
a
Reaction conditions: benzyl amine 1 0.2 mmol, copper catalyst 10 mol%,
t
Ru(bpy)
Cl
3 2
·6H
2
O 2 mol%, LiOBu 20 mol%, solvent 1.6 mL, room temperature,
time 18 h. b GC yield. No light and the ambient is dark. LiOBu is free. e the
c
d
t
f
volume of solvent is 1.2mL. the volume of solvent is 1.0 mL.
t
2a/%b
0c
The above results show that Ru(bpy)
3
Cl
2
/CuBr/LiOBu /DMSO
Entry
Photocatalyst
Transition metal catalyst
is an efficient combination for the synthesis of nitriles from
amines. Using the optimized conditions, we next explored the
scope and generality of the process (Table 3). It was found that
benzylic amines carrying electron-donating and electron-
withdrawing groups could be smoothly converted into the
desired products with good to excellent isolated yields (up to
1
2
3
4
5
6
7
8
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
·6H
·6H
·6H
·6H
·6H
·6H
·6H
·6H
2
O
-
-
2
O
5
2
O
PdCl
Pd(OAc)
CoCl
NiCl
FeCl
CuCl
2
22
20
29
12
10
68
2
O
2
2
O
2
2
O
2
9
5%, entries 1–5). Benzylic amines carrying an ortho-
substituent were also found to readily participate in the
2
O
3
2
O
a
reaction (83–94%, entries 6–9). Electron-donating and electron-
withdrawing groups, ranging from −OMe to −CF groups, were
3
well tolerated in the reactions. The catalyst is also tolerant of
molecules containing heteroatoms such as nitrogen and sulfur.
Heteroatom-containing amines reacted smoothly to afford the
corresponding nitriles in moderate yields (50–63%, entries 10,
Reaction conditions: benzyl amine 1a 0.2 mmol, transition metal catalyst 10
t
mol%, Ru(bpy)
temperature, time 18 h. b GC yield. LiOBu is free.
3 2
Cl ·6H
2
O 2 mol%, LiOBu 20 mol%, DMSO 1.6 mL, room
c
t
Next, different copper salts were evaluated in the
photocatalyzed oxidation of benzylamine (Table 2, entries 1-7).
It was found that yield of product 2a is 67-77% when cuprous
salts were used, while cupric salts gave lower yields. For
instance, CuBr, when combined with Ru(bpy)
oxidation product in 77% yield (entry 2). However, CuBr
gave 29% product (entry 4). Gratifyingly, the result of Cu(OAc)
1
1). In addition, aliphatic amines also could be converted into
nitriles under the standard conditions, and good yields were
obtained by increasing the reaction time (entries 12, 13).
3
Cl
2
, resulted in the
2
only
Table 3. Substrates scope of the visible-light-induced aerobic oxidation of
2
a
amine to nitrile reaction
is good, and 71% yield was obtained (entry 7). We speculated
that the counter anion influenced the catalytic activity.
3 2
Noteworthily, if the photocatalyst of Ru(bpy) Cl was removed,
we did not obtain the designed product (entry 8). Also, when no
light was used to irradiate the reaction, the oxidation product
could not be obtained (entry 9). Moreover, catalytic amount of
Entry
1
1
2
Yield/% b
78
t
LiOBu seems to be essential to achieve a high yield, and 18%
t
yield was produced in the absence of LiOBu (entry 10). Then,
we evaluated different solvents for cooperative catalysis. DMF
gave comparative yield 75% (entry 11), but only 5% of product
was produced in MeCN (entry 12). Finally, the concentration of
reaction mixture slightly influenced the results, and the yield
can be improved to 82% in 1.2mL of DMSO (entry 13).
1
a
2a
2
3
4
5
77
1
b
2b
2c
2d
Table 2. Optimization of the cooperative catalysis of Ru(bpy)
3
Cl and copper
2
95 c
in the aerobic oxidation of amine to nitrile reaction a
1
c
45(65)d
66(85)d
Entry
Photocatalyst
Copper catalyst Solvent 2a/%b
1
d
1
2
3
4
Ru(bpy)
Ru(bpy)
Ru(bpy)
Ru(bpy)
3 2
Cl
3 2
Cl
3 2
Cl
3 2
Cl
·6H
·6H
·6H
·6H
2
O
CuI
CuBr
CuCl
DMSO
DMSO
DMSO
DMSO
67
77
68
29
2
O
2
O
2
O
CuBr
2
1e
2e
2
| J. Name., 2012, 00, 1-3
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DOI: 10.1039/C6OB02510B
6
83
1
f
2f
7
8
9
73(94)d
93 c
1
g
2g
2h
2i
1
h
Scheme 3 Plausible reaction mechanism.
88
1
i
Conclusions
1
0
1
63
To summarize, in the present study we developed a visible-
light-initiated homogeneous oxidative synthesis of nitriles from
amines. Through the combination of photoredox and copper
catalysis, the conversion of amines into nitriles was realized
1
j
2j
1
50d,e
1
k
2k
2l
with O as the oxidant. This new protocol combines copper with
2
photoredox in a single reaction system and shows great
substrate tolerance providing efficient access to a variety of
nitriles in a highly concise fashion. Further studies on the
mechanism of this visible-light mediated process is underway.
1
1
2
3
61e
64e
1
l
1
m
2m
a
reaction conditions: amine 1 0.5 mmol, CuBr 10 mol%, Ru(bpy)
3
Cl
2
b
·6H O 2
2
t
mol%, LiOBu 20 mol%, DMSO 3.0 mL, room temperature, time 18 h. Isolated
yield. Volume of DMSO = 1 mL. GC yield. e Reaction time = 36 h.
c
d
Acknowledgments
We are grateful to National Science Foundation of China
21402062), Natural Science Foundation of Jiangsu Province
BK20130404), Scientific and Technological Research Project of
Lianyungang (CG1303, CG1401), Jiangsu Key Laboratory of
Marine Pharmaceutical Compound Screening (2015HYB11), and
the Project Funded by the Priority Academic Program
Development of Jiangsu Higher Education Institutions.
The new amine oxidation method was effective on a larger
scale (Scheme 2): amine 1c underwent efficient oxidation on a
0 mmol scale, resulting in an 86% isolated yield of the nitrile,
even with decreased photocatalyst loading (0.5 mol %).
(
(
1
References
1
(a) A. J. Fatiadi in Preparation and Synthetic Applications of
Cyano Compounds (Eds.: S. Patai, Z. Rappaport), Wiley, New
York, 1983; (b) A. Kleemann, J. Engel, B. Kutscher, D. Reichert,
Pharmaceutical Substance: Synthesis Patents, Applications,
Scheme 2 Gram-scale synthesis of nitrile
While a precise reaction mechanism awaits further study, a
plausible catalytic cycle is proposed in Scheme 3. Initially, the
copper(I) catalyst underwent ligand exchange to generate
4
th ed., Georg Thieme, Stuttgart, 2001. (c) J. S. Miller, J. L.
Manson, Acc. Chem. Res. 2001, 34, 563. (d) M. B. Smith, J.
March, March’s Advanced Organic Chemistry: Reactions,
Mechanisms, and Structure, 6th ed., Wiley, Hoboken, NJ,
1
2c,12d
*
2+
copper amide
the amide
A
.
Reductive quenching of [Ru(bpy)
3
]
by
+
A
gave intermediate
B
and [Ru(bpy)
3
] which reduce
2
007.
(a) Review: Z. Shi, C. Zhang, C. Tang, N. Jiao, Chem. Soc. Rev.,
012, 41, 3381. (b) G. Yuan, J. Zheng, X. Gao, X. Li, L. Huang,
13
molecular oxygen to the superoxide radical anion. Then, the
superoxide radical anion abstracts a hydrogen atom from the
2
2
1
3a,13b
radial cation
was neutralized by a hydrogen peroxide anion to produce
copper amide . The second reductive quenching cycle
happened to convert intermediate into radial cation . The
hydrogen atom of imine radial cation was grabbed by a
superoxide radical anion to form intermediate , which
furnished the desired product nitrile and a copper(I) salt.
B
to form intermediate
C
.
The iminium ion
C
H. Chen, H. Jiang, Chem. Commun., 2012, 48, 7513. (c) Q.
Kang, Y. Zhang, Green Chem., 2012, 14, 1016. (d) W. Gao, Z.
He, Y. Qian, J. Zhao, Y. Huang, Chem. Sci., 2012, 3, 883. (e) D.
D
Yang, H. Yang, H. Fu, Chem. Commun., 2011, 47, 2348. (f) Y.
Wang, X. Zhu, S. Chiba, J. Am. Chem. Soc., 2012, 134, 3679. (g)
G. Zhang, Y. Ma, S. Wang, Y. Zhang, R. Wang, J. Am. Chem.
Soc., 2012, 134, 12334. (h) A. E. Wendlandt, A. M. Suess, S. S.
Stahl, Angew. Chem. Int. Ed., 2011, 50, 11062.
C. Tao, F. Liu, Y. Zhu, W. Liu, Z. Cao, Org. Biomol. Chem. 2013,
11, 3349.
D
E
E
F
1
3
This journal is © The Royal Society of Chemistry 20xx
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Org aP nl ei ca s &e dB oi o nmo to al ed cj uu sl at rm Ca hr ge imn si stry
Page 4 of 4
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Journal Name
4
(a) W. Yin, C. Wang, Y. Huang, Org. Lett. 2013, 15, 1850. (b) L.
M. Dornan, Q. Cao, J. C. A. Flanagan, J. J. Crawford, M. J. Cook,
M. J. Muldoon, Chem. Commun. 2013, 49, 6030. (c) Q. Feng,
Q. Song, Adv. Synth. Catal. 2014, 356, 1697. (d) R. A. Molla, K.
Ghosh, K. Tuhina, S. M. Islam, New J. Chem. 2015, 39, 921. (e)
L. Zhang, P. Lu, Y. Wang, Org. Biomol. Chem. 2015, 13, 8322.
(a) X. Lang, H. Ji, C. Chen, W. Ma, J. Zhao, Angew. Chem., Int.
Ed. 2011, 50, 3934. (b) N. Li, X. Lang, W. Ma, H. Ji, C. Chen, J.
Zhao, Chem. Commun. 2013, 49, 5034. (c) S. Furukawa, Y.
Chang, J. Rong, J. Chen, W. Xiao, Angew. Chem.VIinewt.AErtdic.le2O0n1lin1e,
DOI: 10.1039/C6OB02510B
Jørgensen, W. Xiao, Angew. Chem. Int. Ed. 2012, 51, 784.
50, 7171. (c) Y. Zou, J. Chen, X. Liu, L. Lu, R. L. Davis, K. A.
5
Ohno, T. Shishido, K. Teramura, T. Tanaka, ACS Catal. 2011,
150. (d) S. Sarina, H. Zhu, E. Jaatinen, Q. Xiao, H. Liu, J. Jia, C.
Chen, J. Zhao, J. Am. Chem. Soc. 2013, 135, 5793. (e) S.-i. Naya,
K. Kimura, H. Tada, ACS Catal. 2012, , 10. (f) D. S.
Ovoshchnikov, B. G. Donoeva, V. B. Golovko, ACS Catal. 2015,
1,
1
3
5
5
, 34. (g) J. Wang, S. Lu, X. Cao, H. Gu, Chem. Commun. 2014,
0
, 5637. (h) D. Damodara, R. Arundhathi, P. R. Likhar, Adv.
Synth. Catal. 2014, 356, 189.
6
7
J. Kim, S. S. Stahl, ACS Catal. 2013, 3, 1652.
(a) J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev.
2
2
011, 40, 102. (b) J. Xuan, W.-J. Xiao, Angew. Chem. Int. Ed.
012, 51, 6828. (c) C. K. Prier, D. A. Rankic, D. W. C. MacMillan,
Chem. Rev. 2013, 113, 5322. (d) Y. Xi, H. Yi, A. Lei, Org. Biomol.
Chem. 2013, 11, 2387. (e) D. M. Schultz, T. P. Yoon, Science
2
014, 343, 985. (f) R. A. Angnes, Z. Li, C. R. D. Correia, G. B.
Hammond, Org. Biomol. Chem. 2015, 13, 9152. (g) M.
Oelgemoller, N. Hoffmann, Org. Biomol. Chem. 2016, 14
392. (h) J. Dai, W. Zhang, Y. Shu, Y. Sun, J. Xu, Y. Feng, H. Xu,
,
7
Chem. Commun. 2016, 52, 6793. (i) X. J. Wei, L. Wang, S. F.
Du, L. Z. Wu, Q. Liu, Org. Biomol. Chem. 2016, 14, 2195. (j) T.
Yang, H. Zhu, W. Yu, Org. Biomol. Chem. 2016, 14, 3376. (k)
B. Li, D. Fan, C. Yang, W. J. Xia, Org. Biomol. Chem. 2016, 14
293. (l) V. K. Y. Lo, A. O. Y. Chan, C. M. Che, Org. Biomol.
Chem. 2015, 13, 6667.
(a) M. N. Hopkinson, B. Sahoo, J. Li, F. Glorius, Chem. Eur. J.
014, 20, 3874. (b) M. D. Levin, S. Kim, F. D. Toste, ACS Cent.
Sci. 2016, , 293. (c) K. L. Skubi, T. R. Blum, T. P. Yoon, Chem.
Rev. 2016, 116, 10035. (d) X. Lang, J. Zhao, X. Chen, Chem.
Soc. Rev., 2016, 45, 3026.
(a) Z. Zuo, D. T. Ahneman, L. Chu, J. A. Terrett, A. G. Doyle,
D.W. MacMillan, Science 2014, 345, 437. (b) J. C. Tellis, D. N.
Primer, G. A. Molander, Science 2014, 345, 433. (c) D. R. Heitz,
,
5
8
9
2
2
J. C. Tellis, G. A. Molander, J. Am. Chem. Soc. 2016, 138
,
1
2715. (d) Z. Duan, W. Li, A. Lei, Org. Lett. 2016, 18, 4012. (e)
M. S. Oderinde, M. Frenette, D. W. Robbins, B. Aquila, J. W.
Johannes, J. Am. Chem. Soc. 2016, 138, 1760. (f) E. B.
Corcoran, M. T. Pirnot, S. Lin, S. D. Dreher, D. A. DiRocco, I. W.
Davies, S. L. Buchwald, D. W. C. MacMillan, Science 2016, 353
79.
,
2
1
0 (a) M. Osawa, H. Nagai, M. Akita, Dalton Trans. 2007, 827. (b)
D. Kalyani, K. B. McMurtrey, S. R. Neufeldt, M. S. Sanford, J.
Am. Chem. Soc. 2011, 133, 18566. (c) S. R. Neufeldt, M. S.
Sanford, Adv. Synth. Catal. 2012, 354, 3517. (d) J. Xuan, T.
Zeng, Z. Feng, Q. Deng, J. Chen, L. Lu, W. Xiao, H. Alper,
Angew, Chem. Int. Ed. 2015, 54, 1625.
1
1
1 (a) B. Sahoo, M. N. Hopkinson, F. Glorius, J. Am. Chem. Soc.
2
013, 135, 5505. (b) X.-Z. Shu, M. Zhang, Y. He, H. Frei, F. D.
Toste, J. Am. Chem. Soc. 2014, 136, 5844. (c) M. N. Hopkinson,
B. Sahoo, F. Glorius, Adv. Synth. Catal. 2014, 356, 2794.
2 (a) Y. Ye, M. S. Sanford, J. Am. Chem. Soc. 2012, 134, 9034. (b)
Y. Ye, S. A. Kunzi, M. S. Sanford, Org. Lett. 2012, 14, 4979. (c)
W. Yoo, T. Tsukamoto, S. Kobayashi, Org. Lett. 2015, 17, 3640.
(d) W. Yoo, T. Tsukamoto, S. Kobayashi, Angew. Chem. Int. Ed.
2015, 54, 6587. (e) W. Iali, P. Lanoe, S. Torelli, D. Jouvenot, F.
Loiseau, C. Lebrun, O. Hamelin, S. Ménage, Angew. Chem. Int.
Ed. 2015, 54, 8415. (f) H. Zhang, D. Chen, Y. Han, Y. Qiu, D. Jin,
X. Liu, Chem. Commun. 2016, 52, 11827.
1
3 (a) A. G. Condie, J. C. González-Gómez, C. R. J. Stephenson, J.
Am. Chem. Soc., 2010, 132, 1464. (b) Y. Zou, L. Lu, L. Fu, N.
4
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