Monofluoromethylation of tetrahydroisoquinolines by visible-light induced direct C(sp3)-H bond activation

Article abstract of DOI:10.1002/adsc.201401146

A visible-light photoredox-catalyzed reaction of tetrahydroisoquinolines with β-fluorinated gem-diols results in the formation of C1-monofluoromethylated tetrahydroisoquinolines via C(sp³)-H bond activation. This protocol provides a new method to introduce a CF group with stable, easily-prepared monofluorinated gem-diol as CF source. A mechanistic investigation is presented based on control experiments.

Full text of DOI:10.1002/adsc.201401146

UPDATES
DOI: 10.1002/adsc.201401146
Monofluoromethylation of Tetrahydroisoquinolines by Visible-
3
À
light Induced Direct C(sp ) H Bond Activation
Weipeng Li,a Yunhuang Zhu,a Yingqian Duan,a Muliang Zhang,a
and Chengjian Zhua,b,*
a
State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University,
Nanjing 210093, People’s Republic of China
E-mail: cjzhu@nju.edu.cn
b
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, People’s Republic of China
Received: December 8, 2014; Revised: February 3, 2015; Published online: && &&, 0000
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201401146.
Abstract: A visible-light photoredox-catalyzed reac-
tion of tetrahydroisoquinolines with b-fluorinated
fluoroalkylation methods under mild conditions re-
mains in high demand. Visible-light photoredox catal-
ysis has been applied to fluoromethylations.[8] Recent-
ly, our group achieved visible-light-induced difluoro-
methylation of tetrahydroisoquinolines with b,b-di-
fluorinated gem-diols as CF2 sources.[9] It was found
that generation of nucleophilic a-fluoroenolates with
b-fluorinated gem-diols is an efficient strategy to in-
stall CF group into useful scaffolds.[10] Given our in-
gem-diols results in the formation of C1-monofluor-
3
À
omethylated tetrahydroisoquinolines via C(sp ) H
bond activation. This protocol provides a new
method to introduce a CF group with stable, easily-
prepared monofluorinated gem-diol as CF source.
A mechanistic investigation is presented based on
control experiments.
À
terest in visible-light promoted C H bond activa-
tion[11] and in consideration of the importance of
fluoro-containing organic compounds, herein we
report monofluoromethylation of tetrahydroisoquino-
lines with easily-prepared trifluoromethyl b-fluorinat-
ed gem-diols as CF sources.
3
À
Keywords: C(sp ) H activation; monofluoromethy-
lation; photoredox catalytic; tetrahydroisoquino-
lines.; visible light
We started our investigation by subjecting N-phenyl
substituted tetrahydroisoquinoline 1a and a-trifluoro-
The direct functionalization of C(sp ) H bonds pro- methyl b-fluorinated gem-diol 2a in the presence of
3
À
vides a potent strategy to access numerous complex catalytic amount of commercial available Ru(b-
molecules,[1] as C(sp ) H bonds are universal in or- py)3Cl2. With air as the oxidant, tetrahydroisoquino-
3
À
ganic compounds. Despite the great achievements in
this area, the development of a mild and effective
3
À
method to activate C(sp ) H bond with clean and re-
newable energy is of high interest. Visible light is an
abundant and non-polluting energy source in nature.
For the past few years, visible-light induced photore-
dox catalysis has aroused more and more attention,[2]
and some fundamental chemical transformations have
been brought out via visible light irradiation.[3] In this
3
À
context, direct activation of C(sp ) H bonds promot-
ed by visible-light has been well developed
(Scheme 1-a).[4,5]
Fluoroalkyl containing organic compounds are of
great importance due to their special biological prop-
erties, such as binding affinity, and bioavailability.[6]
Over the past decades, many methods have been
demonstrated to introduce fluoroalkyl groups into
Scheme 1. Photoredox catalytic functionalization of tetrahy-
useful molecules,[7] but the development of practical droisoquinolines.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
1
ÞÞ
These are not the final page numbers!

UPDATES
Weipeng Li et al.
Table 1. Optimization of reaction conditions[a]
tained the expected product in 55% yield (Table 1,
Entry 1). Encouraged by this result, we then surveyed
different photocatalysts, additives and solvents
(Table 1, Entries 2–15). First, a range of iridium and
ruthenium photocatalysts (Figure 1) were tested
(Table 1, Entries 1–4), [Ru(phen)3]Cl2 (5b) was
chosen as a catalyst for further study because it exhib-
ited best reaction yield. A careful survey of solvents
was then performed, which revealed CH2Cl2 as opti-
mal (Table 1, Entries 3, 6–9). To further improve the
yield, various bases were investigated (Table 1, En-
tries 10–15), which indicated that NEt3 showed the
best result (Table 1, Entry 10). However, all of the
bases tested provided poor diastereoselectivity. Final
optimization showed that the reaction could also pro-
vide comparable result with prolonged reaction time
when the catalyst loading was reduced to 1 mol%
(Table 1, Entry 16). Control experiments indicated
that only a small amount of desired product was gen-
erated without light and catalyst (Table 1, entries 17,
18), and no product was detected without DNB as ox-
idant (Table 1, Entry 19). The reaction showed the
best reactivity with 2 mol% [Ru(phen)3]Cl2, 1.5
equivalents of DNB and 1.5 equivalents of triethyla-
mine under irradiation by 5W blue LED (Table 1,
Entry 10).
Entry Cat. Solvent Base
Yield [%][b] dr[c]
1
2
3
4
5
6
7
8
5a
5b
5c
DCM
DCM
DCM
DCM
DCE
DABCO
DABCO
DABCO
DABCO
DABCO
55
65
40
26
29
56
trace
18
15
1.2:1
1.2:1
1.2:1
ND
1.2:1
1.2:1
ND
1.2:1
ND
1.3:1
1.2:1
1.2:1
1:1.2
1.2:1
1.4:1
1.3:1
–
5d
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
5b
CH3CN DABCO
THF
DABCO
DABCO
DABCO
NEt3
DIPEA
2,6-lutidine 41
Na2CO3
K2CO3
K3PO4
NEt3
NEt3
NEt3
DMF
DMSO
DCM
DCM
DCM
DCM
DCM
DCM
DCM
DCM
DCM
DCM
9
10
11
12
13
14
15
16[d]
17[e]
18[f]
19[g]
73
57
52
58
20
68
trace
trace
NR
–
–
NEt3
With the optimal reaction conditions established,
we then explored the substrates scope of the visible-
light induced photoredox reaction. First, various N-
aryltetrahydroisoquinolines were tested, and the cor-
responding results were showed in Table 2. The posi-
tion of substituents on the N-aryl groups also signifi-
cantly influenced the reaction results. Generally, para-
substituted substrates (Table 2, Entries 2–6) proved
products in very good yields, whereas meta-substitut-
ed and ortho-substituted substrates (Table 2, En-
tries 10–13) resulted in moderate to good yields. The
investigation of substituents effect showed that sub-
[a]
Reaction conditions: 1a (0.2 mmol), 2a (0.24 mmol),
DNB (0.3 mmol), cat. (2 mol%), base (0.3 mmol), sol-
vent (1 mL), irradiated with a 5W blue LED for 48 h
under Ar at r.t.
[b]
[c]
[d]
[e]
[f]
Isolated yield.
Determined by H NMR.
1
1 mol% catalyst irradiated with a 5W blue LED for 60 h.
No catalyst.
No light.
No DNB. DNB=1,3-dinitrobenzene. ND=not deter-
mined. NR=no reaction.
[g]
line 1a was rapidly consumed, but only a 29% yield strates bearing electron-donating groups furnished
of the desired product was obtained (see Table S1 in higher yields than substrates with electron-withdraw-
the SI). The side reaction to the oxidized amide was ing groups. When a strong electron-withdrawing CF3
the main reason responsible for the low yield. In group was installed on the N-substituted aromatic
order to improve the yield, we tested different oxi- ring, the reaction proceeded sluggishly and only 26%
dants (see Table S1 the in SI). Finally, we chose meta- yield was obtained, but with good diastereoselectivity
dinitrobenzene (DNB) as an ideal oxidant and ob- (Table 2, Entry 8). When the substituted tetrahydroi-
Figure 1. Iridium and ruthenium photocatalysts.
2
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

UPDATES
Monofluoromethylation of Tetrahydroisoquinolines
Table 2. The reaction scope of tertiary amines[a]
Table 3. (Continued)
Entry
4
Product[b]
Yield [%][c] dr[d]
5
4 f
72
71
79
66
73
76
42
1.5:1
1.1:1
1.3:1
1.2:1
1.3:1
2:1
Entry
Ar
1
3
Yield [%][b]
dr[c]
1
2
3
4
5
6
7
Ph
1a
1b
1c
1d
1e
1 f
1g
1h
1i
3a
3b
3c
3d
3e
3 f
3g
3h
3i
73
71
64
60
85
88
78
26
80
61
59
65
57
1.3:1
3:1
2.5:1
2:1
1.2:1
1.3:1
1.1:1
>10:1
1.1:1
2:1
6
4g
4h
4i
4-F-C6H4
4-Cl-C6H4
4-Br-C6H4
4-Me-C6H4
4-tBu-C6H4
3,4-Me-C6H4
4-CF3-C6H4
Ph
3-F-C6H4
3-Br-C6H4
3-Me-C6H4
2-F-C6H4
7
8[d]
9[e]
10
11
12
13
1j
1k
1l
3j
3k
3l
3:1
1.3:1
1.5:1
8
1m
3m
[a]
Reaction conditions: see details in Experimental Section.
Isolated yield.
Determined by H NMR.
Reaction time: 72 h.
6,7-Dimethoxy substituted tetrahydroisoquinoline was
used.
[b]
[c]
[d]
[e]
1
9
4j
4k
4l
10
Table 3. The reaction scope of b-fluorinated gem-diols[a]
11
>10:1
Entry
1
4
Product[b]
Yield [%][c] dr[d]
[a]
Reaction conditions: see details in Experimental Section.
Ar=4-Me-C6H4.
[b]
[c]
[d]
Isolated yield.
Determined by H NMR.
1
4b
63
69
75
68
1.3:1
1.2:1
1.2:1
1.2:1
soquinoline derivative 1i was employed, the desired
product 3i could be isolated in 80% yields (Table 2,
Entry 9).
2
3
4
4c
4d
4e
We next sought to investigate the scope of b-fluori-
nated gem-diols in this reaction. As shown in Table 3,
a variety of structurally diverse compounds undergo
efficient reaction with N-aryltetrahydroisoquinoline
1e. Substrates with various electron-donating or elec-
tron-withdrawing groups on the aromatic rings were
compatible in the reaction (Table 3, Entries 1–9). Het-
eroarenes such as thiophene also showed good result
(Table 3, Entry 10). Note that an aliphatic substituted
substrate could provide the corresponding product in
42% yield (Table 3, Entry 11).
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
3
ÞÞ
These are not the final page numbers!

UPDATES
Weipeng Li et al.
Furthermore, an additional scale-up experiment
was performed to show the potential of this method
in practical application (Scheme 2). By treatment of
1a (4.8 mmol, 1 g) with 2a (5.8 mmol, 1.46 g) in the
presence of 2 mol% 5b, the desired product was ob-
tained in 85% yield (1.4 g), showing that this protocol
could be suitable for large-scale synthesis.
Scheme 2. Scale-up experiment.
Then we engaged in exploring the possible mecha-
nism of this reaction. First, we conducted the reaction
without the presence of NEt3. To our surprise, besides
the decarboxylated product 3a, we also detected com-
pound 4a in 18% yield (Scheme 3-a). To determine
the relationship between 3a and 4a, we isolated pure
4a and subjected it to the optimized conditions, and
no decarboxylated product 3a was generated
(Scheme 3-b). This indicated that 3a was not derived
À
through C C bond cleavage of 4a. As shown in
Scheme 3-c, exposure of 6a[12] and N-phenyl tetrahy-
droisoquinoline 1a to the optimized conditions pro-
vided no desired product, suggesting that Mannich ad-
dition took place before the release of trifluoroace-
tate.
Based on the studies described above, we propose
a plausible mechanism (Scheme 4). At first, iminium
1b is formed by SET/dehydrogenation procedures
under photocatalysis conditions.[3b,f] Coupling of this
highly active intermediate with 2b (enolization forma-
tion of 2a) provides intermediate 5a, which could fur-
Scheme 3. Investigation of possible mechanism.
Scheme 4. Possible mechanism.
4
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

UPDATES
Monofluoromethylation of Tetrahydroisoquinolines
References
ther participates in next transformation in two possi-
ble pathways: a) loss of trifluoroacetate from inter-
mediate 5a to give desired product 3a and b) dehy-
dration of 5a to give 4a (Scheme 4-a). Under alkaline
condition, intermediate 5a prefers to undergo C C
bond cleavage, resulting in 3a as the major product
(Scheme 4-b).
In summary, we have developed a mild monofluor-
omethylation of tetrahydroisoquinolines via visible
light-induced photoredox catalysis with stable and
easily-obtained b-fluorinated gem-diols as the CF
source. This transformation allowed us to introduce
the CF group to the corresponding tetrahydroisoqui-
nolines in good yields. Preliminary investigations pro-
vide a general understanding of the reaction mecha-
nism.
[1] Recent reviews: a) S. A. Girard, T. Knauber, C.-J. Li,
Angew. Chem. 2014, 126, 76–103; Angew. Chem. Int.
Ed. 2014, 53, 74–100; b) J. Xie, C. Pan, A. Abdukader,
C.-J. Zhu, Chem. Soc. Rev. 2014, 43, 5245–5256; c) C.
Sun, B. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293–1314.
[2] Representative reviews: a) M. N. Hopkinson, B. Sahoo,
J. Li, F. Glorius, Chem. Eur. J. 2014, 20, 3874–3886;
b) J. Xie, H. Jin, P. Xu, C. Zhu, Tetrahedron Lett. 2014,
55, 36–48; c) C. K. Prier, D. A. Rankic, D. W. C. Mac-
Millan, Chem. Rev. 2013, 113, 5322–5363; d) J. Xuan,
W. Xiao, Angew. Chem. 2012, 124, 6934–6944; Angew.
Chem. Int. Ed. 2012, 51, 6828–6838.
[3] Recent examples: a) X.-D. Xia, Y.-L. Ren, J.-R. Chen,
X.-L. Yu, L.-Q. Lu, Y.-Q. Zou, J. Wan, W.-J. Xiao,
Chem. Asian J. 2015, 10, 124–128; b) X.-Q. Hu, J.-R.
Chen, Q. Wei, F.-L. Liu, Q.-H. Deng, A. M. Beauche-
min, W.-L. Xiao, Angew. Chem. 2014, 126, 12359–
12363; Angew. Chem. Int. Ed. 2014, 53, 12163–12167;
c) W. Ding, Q.-Q. Zhou, J. Xuan, T.-R. Li, L.-Q. Lu,
W.-J. Xiao, Tetrahedron Lett. 2014, 55, 4648–4652; d) H.
Sun, C. Yang, R. Lin, W. Xia, Adv. Synth. Catal. 2014
356, 2775–2780; e) Q. Meng, T. Lei, L. Zhao, C. Wu, J.
Zhong, X. Gao, C. Tung, L.-Z. Wu, Org. Lett. 2014, 16,
5968–5971; f) Z. Zuo, D. T. Ahneman, L. Chu, J. A.
Terrett, A. G. Doyle, D. W. C. MacMillan, Science 2014,
345, 437–440; g) D. A. Nicewicz, D. W. C. MacMillan,
Science 2008, 322, 77–80.
[4] Selected examples: a) G. Bergonzini, C. S. Schindler, C.
Wallentin, E. N. Jacobsen, C. R. J. Stephenson, Chem.
Sci. 2014, 5, 112–116; b) D. A. DiRocco, T. Rovis, J.
Am. Chem. Soc. 2012, 134, 8094–8097; c) S. Zhu, M.
Rueping, Chem. Commun. 2012, 48, 11960–11962;
d) M. Rueping, J. Zoller, D. C. Fabry, K. Poscharny,
R. M. Koenigs, T. E. Weirich, J. Mayer, Chem. Eur. J.
2012, 18, 3478–3481; e) Y.-Q. Zou, L.-Q. Lu, L. Fu, N.-
J. Chang, J. Rong, J.-R. Chen, W.-J. Xiao, Angew.
Chem. 2011, 123, 7309–7313; Angew. Chem. Int. Ed.
2011, 50, 7171–7175; f) A. G. Condie, J. C. Gonzalez-
Gomez, C. R. J. Stephenson, J. Am. Chem. Soc. 2010,
132, 1464–1465.
[5] a) A. G. Condie, J. C. Gonzalez-Gomez, C. R. J. Ste-
phenson, J. Am. Chem. Soc. 2010, 132, 1464–1465;
b) M. Rueping, S. Zhu, R. M. Koenigs, Chem.
Commun. 2011, 47, 8679–8681; c) M. Rueping, R. M.
Koenigs, K. Poscharny, D. C. Fabry, D. Leonori, C. Vila,
Chem. Eur. J. 2012, 18, 5170–5174; d) W. Fu, W. Guo,
G. Zou, C. Xu, J. Fluor. Chem. 2012, 140, 88–94.
À
Experimental Section
General Procedure
To a 10 mL Schlenk flask equipped with a magnetic stir bar
was added tetrahydroisoquinoline (0.2 mmol), b-fluorinated
gem-diol (0.24 mmol), DNB (0.3 mmol), and [Ru(phen)3]Cl2
(5b, 0.004 mmol, 2 mol%). The tube was degassed by alter-
nating vacuum evacuation (5 min) and argon backfill three
times. CH2Cl2 (1 mL) was added followed by NEt3
(0.3 mmol). The mixture was then irradiated with a 5W blue
LED 200 cm strip at room temperature for 48 h. After the
starting material was consumed as indicated by TLC, the
mixture was subjected to flash chromatography (petroleum
ether 60–90/EtOAc, 15:1) on silica gel to give the desired
product.
Procedure of Scale-up Experiment
To a 50 mL Schlenk flask equipped with a magnetic stir bar
was added tetrahydroisoquinoline 1a (4.8 mmol, 1.0 g), b-
fluorinated gem-diol 2a (5.8 mmol, 1.46 g), DNB (7.2 mmol,
1.2 g), [Ru(phen)3]Cl2 (5b, 0.096 mmol, 68 mg, 2 mol%).
The tube was degassed by alternating vacuum evacuation
(5 min) and argon backfill three times. CH2Cl2 (24 mL) was
added followed by NEt3 (7.2 mmol, 0.73 g). The mixture was
then irradiated by two 18W white fluorescent light at room
temperature for 3 days. Then the mixture was washed with
brine, dried, and concentrated under reduced pressure. The
residue was purified by column chromatography over silica
gel to give monofluoromethylated tetrahydroisoquinoline 3a
as a yellow oil; yield: 1.4 g (85%).
[6] a) K. Mꢁller, C. Faeh, F. Diederich, Science 2007, 317,
1881–1886; b) S. Purser, P. R. Moore, S. Swallow, V.
Gouverneur, Chem. Soc. Rev. 2008, 37, 320–330.
[7] a) X. Shen, W. Miao, C. Ni, J. Hu, Angew. Chem. 2014,
126, 794–798; Angew. Chem. Int. Ed. 2014, 53, 775–779;
b) X. Shen, M. Zhou, C. Ni, W. Zhang, J. Hu, Chem.
Sci. 2014, 5, 117–122; c) B. Gao, Y. Zhao, M. Hu, C. Ni,
J. Hu, Chem. Eur. J. 2014, 20, 7803–7810; d) K. Zhang,
J. Liu, F.-L. Qing, Chem. Commun. 2014, 50, 14157–
14160; e) L. Chu, F.-L. Qing, Acc. Chem. Res. 2014, 47,
1513–1522; f) X. Wang, G. Liu, X. Xu, N. Shibata, E.
Tokunaga, N. Shibata, Angew. Chem. 2014, 126, 1858;
Angew. Chem. Int. Ed. 2014, 53, 1827; g) X. Jiang, F. L.
Acknowledgements
We gratefully acknowledge the Nature National Science
Foundation of China (21172106, 21074054, 21372114), the
National Basic Research Program of China (2010CB923303)
and the Research Fund for the Doctoral Program of Higher
Education of China (20120091110010) for their financial sup-
port.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
5
ÞÞ
These are not the final page numbers!

UPDATES
Weipeng Li et al.
Qing, Angew. Chem. 2013, 125, 14427–14430; Angew.
Chem. Int. Ed. 2013, 52, 14177–14180; h) P. S. Fier, J. F.
Hartwig, Angew. Chem. 2013, 125, 2146; Angew. Chem.
Int. Ed. 2013, 52, 2092; i) G. K. S. Prakash, C. Ni, F.
Wang, Z. Zhang, R. Haiges, G. A. Olah, Angew. Chem.
2013, 125, 11035; Angew. Chem. Int. Ed. 2013, 52,
10835.
[10] a) I. Saidalimu, X. Fang, X. He, J. Liang, X. Yang, F.
Wu, Angew. Chem. 2013, 125, 5676–5680; Angew.
Chem. Int. Ed. 2013, 52, 5566–5570; b) I. Saidalimu, X.
Fang, W. Lv, X. Yang, X. He, J. Zhang, F. Wu, Adv.
Synth. Catal. 2013, 355, 857–863; c) C. Wu, G. Li, W.
Sun, M. Zhang, L. Hong, R. Wang, Org. Lett. 2014, 16,
1960–1963.
[8] a) L. Wang, X. Wei, W. Jia, J. Zhong, L.-Z. Wu, Q. Liu,
Org. Lett. 2014, 16, 5842–5845; b) J. Jung, E. Kim, Y.
You, E. J. Cho, Adv. Synth. Catal. 2014, 356, 2741–
2748; c) Y. M. Su, Y. Hou, F. Yin, Y. M. Xu, Y. Li, X.
Zheng, X. S. Wang, Org. Lett. 2014, 16, 2958; d) N.
Iqbal, J. Jung, S. Park, E. J. Cho, Angew. Chem. 2014,
126, 549–552; Angew. Chem. Int. Ed. 2014, 53, 539–542;
e) Y. Yasu, Y. Arai, R. Tomita, T. Koike, M. Akita,
Org. Lett. 2014, 16, 780–783; f) Q. Lin, L. Chu, F. L.
Qing, Chin. J. Chem. 2013, 31, 885; g) D. A. Nagib,
M. E. Scott, D. W. C. MacMillan, J. Am. Chem. Soc.
2009, 131, 10875–10877.
[11] a) J. Xie, X. Yuan, A. Abdukader, C. Zhu, J. Ma, Org.
Lett. 2014, 16, 1768–1771; b) Q. Xue, J. Xie, H. Jin, Y.
Cheng, C. Zhu, Org. Biomol. Chem. 2013, 11, 1606–
1609; c) J. Xie, Q. Xue, H. Jin, H. Li, Y. Cheng, C.
Zhu, Chem. Sci. 2013, 4, 1281–1286.
[12] Substrate 2a slowly decomposes into 6a under basic
conditions at room temperature.
[9] W. Li, X. Zhu, H. Mao, Z. Tang, Y. Cheng, C.-J. Zhu,
Chem. Commun. 2014, 50, 7521–7523.
6
asc.wiley-vch.de
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 0000, 000, 0 – 0
ÝÝ
These are not the final page numbers!

UPDATES
Monofluoromethylation of Tetrahydroisoquinolines by
7
3
À
Visible-light Induced Direct C(sp ) H Bond Activation
Adv. Synth. Catal. 2015, 357, 1 – 7
Weipeng Li, Yunhuang Zhu, Yingqian Duan,
Muliang Zhang, Chengjian Zhu*
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢀ 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
asc.wiley-vch.de
7
ÞÞ
These are not the final page numbers!