Visible Light-Induced Photocatalytic C?H Perfluoroalkylation of Quinoxalinones under Aerobic Oxidation Condition

Article abstract of DOI:10.1002/adsc.201900885

An efficient approach using a photocatalytic strategy for C?H perfluoroalkylation of quinoxalinones under aerobic oxidation condition has been developed. Such transformation employs readily available sodium perfluoroalkanesulfinates as perfluoroalkylation reagents and demonstrates good functional group compatibility, affording corresponding products in moderate to good yields. Compared with previous procedures, this protocol uses oxygen as oxidant, and avoids the use of external additive. A radical mechanism is involved in this perfluoroalkylation reaction. (Figure presented.).

Full text of DOI:10.1002/adsc.201900885

Title: Visible Light-Induced Photocatalytic C-H Perfluoroalkylation of
Quinoxalinones under Aerobic Oxidation Condition
Authors: Zhenjiang Wei, Sijia Qi, Yanhao Xu, Hao Liu, Junzhe Wu,
Hong-Shuang Li, Chengcai Xia, and Guiyun Duan
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201900885
Link to VoR: http://dx.doi.org/10.1002/adsc.201900885

10.1002/adsc.201900885
Advanced Synthesis & Catalysis
UPDATE
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Visible Light-Induced Photocatalytic C-H Perfluoroalkylation
of Quinoxalinones under Aerobic Oxidation Condition
Zhenjiang Wei,a Sijia Qi,a Yanhao Xu,a Hao Liu,a Junzhen Wu,a Hongshuang Li,a
Chengcai Xia,a* and Guiyun Duana*
a Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian 271000,
People’s Republic of China
E-mail: xiachc@163.com; gyduan@tsmc.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract: An efficient approach using a photocatalytic
strategy for C-H perfluoroalkylation of quinoxalinones
under aerobic oxidation condition has been developed.
Such transformation employs readily available sodium
perfluoroalkanesulfinates as perfluoroalkylation reagents
and demonstrates good functional group compatibility,
affording corresponding products in moderate to good
yields. Compared with previous procedures, this protocol
uses oxygen as oxidant, and avoids the use of external
additive. A radical mechanism is involved in this
perfluoroalkylation reaction.
Keywords: visible light; photocatalysis; quinoxalinones;
C-H perfluoroalkylation; additive free
Perfluoroalkyl
trifluoromethyl
considerable
compounds,
compounds,
particularly
recieved
Scheme 1. Direct C-H perfluoroalkylation of quinoxalinones
have
Quinoxalinones represent a significant kind of
organic compounds due to the wide distribution in
natural products and pharmaceuticals.[4] Therefore, it
is important to develop efficient methods for the
synthesis of such compounds. Recently, C-H
functionalization reaction has been regarded as an
useful strategy for the synthesis of quinoxalinones
derivatives. Using this strategy, many transformations
have been realized, such as arylation,[5] alkylation,[6]
attention
in
pharmaceuticals,
agrochemicals, and organic materials due to the
unique effect of the fluorine atom on physical and
biological properties of such compounds.[1] In recent
years, C-H trifluoromethylation reaction through
radical
pathway
has
been
emerged
as
one of the most attractive strategies for the synthesis
of trifluoromethyl compounds, and considerable
advances have been achieved in this field so far.[2] For
instances, Liu and co-workers developed a dual-
catalytic strategy to direct asymmetric radical
aminotrifluoromethylation of alkenes in 2016.[2i] In
subsequent works, they disclosed two copper-
catalyzed reaction systems for asymmetric radical
oxytrifluoromethylation of alkenes[2p] and alkenyl
oximes,[2q] respectively. In 2019, Sun, Chu and
coworkers developed a nickel-catalyzed ortho C-H
trifluoromethylation of 8-aminoquinoline by acyl-
directed functionalization.[2s] In stark contrast, C-H
perfluoroalkylation remains scarce.[3] Therefore, the
development of convenient and efficient approach for
C-H perfluoroalkylation is highly desirable, but
challenging.
amination,[7]
acylation,[8]
phosphorization,[9]
fluoroalkoxylation,[10] difluoroarylmethylation,[11] and
difluoroacetylation.[12] In sharp contrast to these, C-H
perfluoroalkylation of quinoxalinones continues to be
scarce, with notable recent advance realized with the
aid of oxidative C-H trifluoromethylation.[13] In 2018,
Zhao, Zhang and co-workers reported a PhI(TFA)2
mediated oxidative C-H trifluoromethylation of
quinoxalinones
using
CF3SO2Na
as
the
trifluoroalkylated reagent (Scheme 1a).[13a] Very
recently, Hu group demonstrated an oxidative C-H
trifluoromethylation
of
quinoxalinones
using
TMSCF3 as the trifluoroalkylated reagent, KF as the
additive, and PhI(OAc)2 as the oxidant (Scheme
1b).[13b] Despite these significant advances, only
1
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10.1002/adsc.201900885
Advanced Synthesis & Catalysis
Table 1. Optimization of reaction conditions[a,b]
Table 3. Scope for perfluoroalkylation of
quinoxalinones[a,b]
Yield
[%]b
62
Entry
Photoatalyst
Solvent
1
2
Rose bengal
Erythrosine
Rhodamine B
Eosin Y
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
DMF
43
3
trace
81
4
−
5
Acr+-Mes ClO4
Ru(bpy)3Cl2
Ir(ppy)3
trace
25
6
7
39
8
-
0
9
Eosin Y
21
10
11
12
13
14
15
16c
17d
18e
19f
20g
21h
Eosin Y
Acetone
MeCN
DCE
THF
1,4-Dioxane
H2O
33
Eosin Y
trace
36
Eosin Y
Eosin Y
trace
trace
trace
62
[a]
Eosin Y
Reaction conditions: 1 (0.2 mmol), 2 (0.6 mmol),
Eosin Y
photocatalyst (5 mol %), DMSO (1.0 mL), blue LED (18
Eosin Y
DMSO
DMSO
DMSO
DMSO
DMSO
DMSO
W), rt, air, 24 h. [b] Isolated yields.
Eosin Y
79
transformations failed to reach the requirements of
atom economy.[14] Therefore, it is still meaningful to
develop simple and atom economic methods for direct
C-H perfluoroalkylation of quinoxalinones.
Eosin Y
49
Eosin Y
0
Eosin Y
trace
80
Eosin Y
[a]
Reaction conditions: 1a (0.2 mmol), 2a (0.6 mmol),
As an alternative pathway to introduce fluorine-
containing functional groups into organic molecules,
visible light-induced photocatalysis recently has
received considerable attention because such strategy
meets the demands of operational simplicity, atom
photocatalyst (5 mol %), solvent (1.0 mL), blue LED (18
W), rt, air, 24 h.
[b] Isolated yields.
[c] 2a (0.4 mmol).
[d] 2a (0.8 mmol).
economy,
and
environmental
friendliness.[15]
[e] White LEDs (18 W).
[f] Without light.
MacMillan and coworkers have disclosed plenty of
pioneering studies.[16] For example, they described a
photocatalyzed trifluoromethylation of electron-rich
arenes and heterocycles with CF3SO2Cl.[16c] Later, a
simple and mild approach for the synthesis of ɑ-
[g] Under N2.
[h] Under O2.
trifluoromethylation was reported in these two
methods. Furthermore, inert gases, excess oxidants
and additives were required. In this regard, such
trifluoromethyl
carbonyl
compounds
by
photocatalysis was demonstrated.[16d] Since then,
significant progress has been made on photocatalytic
C-H
trifluoromethylation.[15c-s]
In
contrast,
Table 2. Scope for trifluoromethylation of
quinoxalinones[a,b]
photocatalytic C-H perfluoroalkylation reaction is
rarely reported.[15t-x] Herein, we reported
a
of
sodium
photocatalytic
quinoxalinones
perfluoroalkanesulfinates
C-H
perfluoroalkylation
using
as
perfluoroalkylation
reagents (Scheme 1c). Unlike the previous works, this
strategy uses oxygen as oxidant, and avoids the use of
external additive. Furthermore, this transformation
can run well under air atmosphere, which simplifies
the operation process.
Table 4. Perfluoroalkylation of xanthine derivatives[a,b]
[a]
[a]
Reaction conditions: 1 (0.2 mmol), 2a (0.6 mmol),
Reaction conditions: 5 (0.2 mmol), 2 (0.6 mmol),
photocatalyst (5 mol %), DMSO (1.0 mL), blue LED (18
photocatalyst (5 mol %), DMSO (1.0 mL), blue LED (18
W), rt, air, 24 h. [b] Isolated yields.
W), rt, air, 24 h. [b] Isolated yields.
2
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10.1002/adsc.201900885
Advanced Synthesis & Catalysis
Figure 1. Visible light irradiation On/Off experiments.
Scheme 2. Gram-scale synthesis and further chemistry
oxygen atmosphere (Table 1, entry 21). These results
implied that such transformation is an aerobic
reaction.
At the outset, we chose quinoxalinone 1a and
CF3SO2Na (Langlois’ reagent) 2a as the model
substrates for the visible light-induced photocatalytic
C-H perfluoroalkylation, the experimental results are
shown in Table 1. Using 5 mol% of Rose bengal as
the photocatalyst and dimethylsulfoxide (DMSO) as
the solvent under the irradiation of 18 W blue LEDs,
the transformation did indeed proceed to give the
desired product 3a in 62% yield (Table 1, entry 1).
Encouraged by the result, we then continued to screen
other photocatalysts such as Erythrosine, Rhodamine
With the optimized reaction conditions in hand, the
substrate
scope
of
trifluoromethylation
of
quinoxalinones was then tested (Table 2). In general,
the transformations displayed good functional group
tolerance. Quinoxalinones with a series of N-
protecting groups such as methyl (-CH3), ethyl (-
CH2CH3), butyl (-CH2CH2CH2CH3), isobutyl (-
CH2CH(CH3)2), cyclohexylmethyl (-CH2Cy) and
esteryl (-CH2CO2R) were well compatible under
standard conditions, providing the corresponding
products (3a–3g) in 72-81% yields.[17] It is worth
noting that quinoxalin-2(1H)-one without protecting
group was tolerated in this transformation, affording
the corresponding product (3h) in 42% yield.
Quinoxalinones bearing substituted N-benzyl groups
(-CH2Ar) were also well compatible, providing the
trifluoromethylated products in 47-77% yields (3i-t).
Quinoxalinones bearing substituents on the benzene
ring were also tested under the optimal reaction
conditions. In general, the electronic effect has great
effects on the reactions. The electron-donating groups
such as methyl (-CH3) and methoxy (-OCH3) were
well compatible, providing the corresponding
products (3u-w) in 72-80% yields. The halogen-
containing substrates, which could be further
functionalized, were also tolerated, giving the
products (3x-y) in good yields. However, substrate
with strong electron-withdrawing group (-COPh)
furnished the product (3z) in a low yield of 38%, and
even no corresponding product (3aa) was produced
by employing the substrate with nitro (-NO2) group.
−
B, Eosin Y, Acr+−Mes ClO4 , Ru(bpy)3Cl2, and
Ir(ppy)3 (Table 1, entries 2-7). To our delight, the
yield was enhanced to 81% by using Eosin Y as the
photocatalyst. No product was detected in the absence
of any photocatalyst (Table 1, entry 8). Subsequently,
we explored the effects of solvents for the reaction.
Various solvents including dimethyl formamide
(DMF), acetone, MeCN, 1,2-dichloroethane (DCE),
tetrahydrofuran (THF), 1,4-dioxane and H2O were
invistigated (Table 1, entries 9-15), however, none of
them was better than dimethylsulfoxide (DMSO). A
lower yield of 62% was gained when 2.0 equivalents
of CF3SO2Na were employed (Table 1, entry 16), but
there was no significant change when the amounts
was enhanced to 4.0 equivalents (Table 1, entry 17).
The trifluoromethylation did also work under the
irradiation of 18 W white LEDs, only leading to a
decrease of product yield (Table 1, entry 18). As
expected, the reaction did not happen without the
irradiation of visible light (Table 1, entry 19). It
should be mentioned that the transformation could not
proceed under nitrogen atmosphere (Table 1, entry
20). Nevertheless, it did also work well under the
Scheme 4. Plausible mechanism
Scheme 3. Control experiments
3
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10.1002/adsc.201900885
Advanced Synthesis & Catalysis
Furthermore, we tested coumarin and 2H- to provide the O2•- species, in which the eosin Y was
benzo[b][1,4]oxazin-2-one respectively under the regenerated. After that, the intermediate B was
standard conditions, and found that the coumarin subsequently oxidized by O2•- species to afford the
2-
could be converted into corresponding product (3ab) intermediate C and O2 . Finally, the deprotonation of
in an acceptable yield.
intermediate C afforded the target product 3a.
Further investigations found that sodium
In conclusion, we have reported a practical method
perfluoroalkanesulfinates (RfSO2Na) with long-chain for C-H perfluoroalkylation of quinoxalinones with
perfluoroalkyl groups were also compatible under sodium perfluoroalkanesulfinates under the irradiation
standard conditions (Table 3). In this case, sodium of blue LEDs. Unlike previous procedures, these
sulfinates such as C4F9SO2Na, C6F13SO2Na, transformations proceed well under air atmosphere
C8F17SO2Na and C2H5O2CCF2SO2Na were explored, and additive free conditions, affording the
affording the corresponding products (4a-n) in 50-79% corresponding products in moderate to good yields.
yields.
The control experiments suggested that a radical
The successful C-H perfluoroalkylation of mechanism was responsible for this reaction.
quinoxalinones encouraged us to explore the
perfluoroalkylation of xanthine, which is an important
biologically active alkaloid.[18] As shown in Table 4.
Experimental Section
The preliminary study found that the standard
reaction condition was also suitable for the C-H
perfluoroalkylation of xanthine derivative. However,
only 25-35% yields of products were obtained.
Further invesigations on the improvement of such
transformation are currently underway in our
laboratory.
General Information
The starting materials, solvents and other chemicals used in
experiments were purchased from Energy Chemical
without further purification. All products were isolated by
short chromatography on a silica gel (200-300 mesh)
column using petroleum ether (60-90°C) and ethyl acetate.
1H, 13C and 19F NMR spectra were recorded on Bruker
Advance DRX-500 spectrometers at ambient temperature
with CDCl3 or DMSO-d6 as solvent and tetramethylsilane
(TMS) as the internal standard. All chemical shift values
are quoted in ppm and coupling constants quoted in Hz.
Compounds for HRMS were analyzed by positive mode
electrospray ionization (ESI) using Agilent 6530 QTOF
mass spectrometer.
To show the scalability of our photocatalytic C-H
perfluoroalkylation
reactions,
the
gram-scale
synthesis was first performed, providing target
products 3a, 4a, 4e, 4i, and 4j in 70%, 67%, 62%,
59%, and 60% yield, respectively (Scheme 2a).
Furthermore, the trifluoromethylated quinoxalinones
could be converted into a variety of substituted
quinoxalines. For example, compound 3h could be
treated by POCl3 to form compound 7, which could
be used in the further Suzuki–Miyaura coupling
reaction (Scheme 2b). Meanwhile, product 3a also
could react with LiAlH4 to give corresponding
product 9 in 91% yield (Scheme 2c).
General procedure for the synthesis of
trifluoromethylated quinoxalin-2(1H)-ones (3a-aa)
Quinoxalin-2(1H)-ones derivatives
1
(0.2 mmol),
CF3SO2Na 2a (0.6 mmol), Eosin Y (0.01 mmol) and
DMSO (1.0 mL) were combined in a 15 mL tube. The
mixture was then stirred for 24 hours at room temperature
under the radiation of 18 W blue LED. After the
To clarify the reaction mechanism, several control
experiments were performed (Scheme 3). The
perfluoroalkylation
reaction
was
completely
suppressed when 2.0 equivalents of TEMPO or DPE
were used as the radical scavenger, respectively. conversion was completed as indicated by TLC, to the
Furthermore, the adduct 10 or 11 was detected
respectively. These phenomena clearly demonstrated
that a radical mechanism was responsible for the
transformation. Furthermore, the results of On/Off
experiments demonstrated that the continuous
irradiation of visible light was indispensable for the
transformation (Figure 1).
residue was added water (10 mL) and extracted with ethyl
acetate (5 mL  3). The collected organic layer was washed
with brine, dried with MgSO4, filtered and concentrated in
vacuo. The residue was purified directly by flash column
chromatography.
General procedure for the synthesis of
trifluoromethylated coumarin (3ab)
Based on previous works[15p-r] and the results of
control experiments, we proposed
a
probable
Coumarin 1ab (0.2 mmol), CF3SO2Na 2a (0.6 mmol),
Eosin Y (0.01 mmol) and DMSO (1.0 mL) were combined
in a 15 mL tube. The mixture was then stirred for 24 hours
at room temperature under the radiation of 18 W blue LED.
After the conversion was completed as indicated by TLC,
to the residue was added water (10 mL) and extracted with
ethyl acetate (5 mL  3). The collected organic layer was
washed with brine, dried with MgSO4, filtered and
concentrated in vacuo. The residue was purified directly by
flash column chromatography.
mechanism for the reaction (Scheme 4). First of all,
the excited eosin Y* was generated under the
irradiation of visible light. Next, a single-electron-
transfer process took place between sodium
trifluoromethanesulfinate and eosin Y* to form the
trifluoromethyl radical and eosinY•- species. Then,
the trifluoromethyl radical attacked substrate 1a to
produce intermediate A, which underwent a 1,2-
hydrogen shift proecss to generate intermediate B.
Meanwhile, another single-electron-transfer (SET)
process took place between eosinY•- species and O2
4
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10.1002/adsc.201900885
Advanced Synthesis & Catalysis
o
General procedure for the synthesis of
1 hours at 160 C. After the conversion was completed as
indicated by TLC, to the residue was added water (5 mL)
and extracted with ethyl acetate (5 mL  3). The collected
organic layer was washed with brine, dried with MgSO4,
filtered and concentrated in vacuo. The residue was
purified directly by flash column chromatography.
perfluoroalkylated quinoxalin-2(1H)-ones (4)
Quinoxalin-2(1H)-ones derivatives 1 (0.2 mmol), RfSO2Na
2 (0.6 mmol), Eosin Y (0.01 mmol) and DMSO (1.0 mL)
were combined in a 15 mL tube. The mixture was then
stirred for 24 hours at room temperature under the radiation
of 18 W blue LED. After the conversion was completed as General procedure for the synthesis of 2-(p-tolyl)-
indicated by TLC, to the residue was added water (10 mL) 3-(trifluoromethyl)quinoxaline (8)
and extracted with ethyl acetate (5 mL  3). The collected
2-Chloro-3-(trifluoromethyl)quinoxaline 7 (0.2 mmol), p-
organic layer was washed with brine, dried with MgSO4,
tolylboronic acid (0.3 mmol), Pd(PPh3)4 (0.01 mmol),
filtered and concentrated in vacuo. The residue was
K2CO3 (0.4 mmol) and toluene (1.5 mL) were combined in
purified directly by flash column chromatography.
o
a 15 mL tube. The mixture was stirred at 115 C under N2
General procedure for the synthesis of
trifluoromethylated xanthine (6a)
atmosphere for 12 hours. After the conversion was
completed as indicated by TLC, to the residue was added
water (5 mL) and extracted with ethyl acetate (5 mL  3).
The collected organic layer was washed with brine, dried
with MgSO4, filtered and concentrated in vacuo. The
residue was purified directly by flash column
chromatography.
Xanthine derivative 5 (0.2 mmol), CF3SO2Na 2a (0.6
mmol), Eosin Y (0.01 mmol) and DMSO (1.0 mL) were
combined in a 15 mL tube. The mixture was then stirred for
24 hours at room temperature under the radiation of 18 W
blue LED. After the conversion was completed as indicated
by TLC, to the residue was added water (10 mL) and General procedure for the synthesis of 1-methyl-3-
extracted with ethyl acetate (5 mL  3). The collected (trifluoromethyl)-3,4-dihydroquinoxalin-2(1H)-one
organic layer was washed with brine, dried with MgSO4, (9)
filtered and concentrated in vacuo. The residue was
LiAlH4 (0.22 mmol) was added to a solution of 1-methyl-3-
purified directly by flash column chromatography.
(trifluoromethyl)quinoxalin-2(1H)-one (0.2 mmol, 1 equiv)
General procedure for the synthesis of
perfluoroalkylated xanthine (6b-d)
in dried THF (2 mL), The mixture was stirred at 0 oC for 1
hour. After the conversion was completed as indicated by
TLC, to the residue was added NaHCO3 solution (5 mL)
and extracted with ethyl acetate (5 mL  3). The collected
organic layer was washed with brine, dried with MgSO4,
filtered and concentrated in vacuo. The residue was
purified directly by flash column chromatography.
Xanthine derivative 5 (0.2 mmol), RfSO2Na 2 (0.6 mmol),
Eosin Y (0.01 mmol) and DMSO (1.0 mL) were combined
in a 15 mL tube. The mixture was then stirred for 24 hours
at room temperature under the radiation of 18 W blue LED.
After the conversion was completed as indicated by TLC,
to the residue was added water (10 mL) and extracted with
ethyl acetate (5 mL  3). The collected organic layer was
washed with brine, dried with MgSO4, filtered and
concentrated in vacuo. The residue was purified directly by
flash column chromatography.
Acknowledgements
We are grateful to the Shandong Provincial Natural
Science Foundation (ZR2017LB006) for financial support.
General procedure for the gram-scale synthesis of
perfluoroalkylated 1-methylquinoxalin-2(1H)-one
(3a, 4a, 4e, 4i and 4j)
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3). The collected organic layer was washed with brine,
dried with MgSO4, filtered and concentrated in vacuo. The
residue was purified directly by flash column
chromatography.
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Advanced Synthesis & Catalysis
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8929; b) J.-W. Yuan, J.-H. Fu, S.-N. Liu, Y.-M. Xiao, P.
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P. Melchiorre, Angew. Chem., Int. Ed. 2014, 53, 4921;
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Int. Ed. 2016, 55, 8740; e) D. Wang, J. Fang, G.-J.
Deng, H. Gong, ACS Sustainable Chem. Eng. 2017, 5,
6398; f) J. Xu, L. Qiao, B. Ying, X. Zhu, C. Shen, P.
Zhang, Org. Chem. Front. 2017, 4, 1116; g) J.-S. Lin,
F.-L. Wang, X.-Y. Dong, W.-W. He, Y. Yuan, S. Chen,
X.-Y. Liu, Nat. Commun. 2017, 8, 14841; h) J.-S. Lin,
T.-T. Li, J.-R. Liu, G.-Y. Jiao, Q.-S. Gu, J.-T. Cheng,
Y.-L. Guo, X. Hong, X.-Y. Liu, J. Am. Chem. Soc.
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Chauvin, X. Cui, Chem. Commun. 2016, 52, 2846; b) J.
Wang, J. Li, Y. Wei, J. Yang, C. Huo, Org. Chem.
Front. 2018, 5, 3534; c) Y. Kim, D. Y. Kim,
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[10] J. Xu, H. Yang, H. Cai, H. Bao, W. Li, P. Zhang, Org.
Lett. 2019, 21, 4698.
[11] G. Hong, J. Yuan, J. Fu, G. Pan, Z. Wang, L. Yang, Y.
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1173.
[12] L. Wang, H. Liu, F. Li, J. Zhao, H.-Y. Zhang, Y.
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2018, 18, 392; for representative examples, see: b) A.
Monge, F. J. Martinez-Crespo, A. Lopez de Cerain, J.
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[13] Two previous examples of C3-H trifluoromethylation
of quinoxalinones, see: a) L. Wang, Y. Zhang, F. Li, X.
Hao, H.-Y. Zhang, J. Zhao, Adv. Synth. Catal. 2018,
360, 3969; b) W. Xue, Y. Su, K.-H. Wang, L. Cao, Y.
Feng, W. Zhang, D. Huang, Y. Hu, Asian J. Org. Chem.
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G. R. Kumar, B.V. S. Reddy, Tetrahedron Lett. 2018,
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H. Xia, J. Wu, Org. Chem. Front. 2016, 3, 1163;
Selected
examples
of
photocatalyzed
C-H
trifluoromethylation, see: c) T. P. Yoon, M. A. Ischay, J,
Du, Nat. Chem. 2010, 2, 527; d) Y. Ye, M. S. Sanford,
J. Am. Chem. Soc. 2012, 134, 9034; e) J. Xie, X. Yuan,
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Bao, W. Liu, C. Hu, D. Yang, H. Wang, ACS
6
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Advanced Synthesis & Catalysis
A. Abdukader, C. Zhu, J. Ma, Org. Lett. 2014, 16,
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Selected
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of
photocatalyzed
C-H
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W. R. Dolbier, Jr., Org. Lett. 2014, 16, 4594; u) C.-Y.
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W. C. MacMillan, Angew. Chem., Int. Ed. 2011, 50,
6119.
[17] CCDC 1941216 contains the supplementary
crystallographic data for compound 3d. These data can
be obtained free of charge from The Cambridge
Crystallographic
Data
Centre
via
www.ccdc.cam.ac.uk/data_request/cif.
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7
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10.1002/adsc.201900885
Advanced Synthesis & Catalysis
UPDATE
Visible Light-Induced Photocatalytic C-H
Perfluoroalkylation of Quinoxalinones under
Aerobic Oxidation Condition
Adv. Synth. Catal. Year, Volume, Page – Page
Zhenjiang Wei,a Sijia Qi,a Yanhao Xu,a Hao Liu,a
Junzhen Wu,a Hongshuang Li,a Chengcai Xia,a*
and Guiyun Duana*
8
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