Three-Component Synthesis of Isoquinoline Derivatives by a Relay Catalysis with a Single Rhodium(III) Catalyst

Article abstract of DOI:10.1021/acs.orglett.9b01456

A rhodium(III)-catalyzed one-pot three-component reaction of N-methoxybenzamide, α-diazoester, and alkyne was developed, providing an alternative way to synthesize isoquinoline derivatives. Mechanistically, it is a relay catalysis, and the reaction occurred via successive O-alkylation and C-H activation processes, both of which were promoted by the same catalyst.

Full text of DOI:10.1021/acs.orglett.9b01456

Letter
pubs.acs.org/OrgLett
Cite This: Org. Lett. XXXX, XXX, XXX−XXX
Three-Component Synthesis of Isoquinoline Derivatives by a Relay
Catalysis with a Single Rhodium(III) Catalyst
Chao Zhou, Jijun Jiang, and Jun Wang*
Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, School of Chemistry, Sun Yat-Sen University,
Guangzhou 510275, P. R. China
S
* Supporting Information
ABSTRACT: A rhodium(III)-catalyzed one-pot three-com-
ponent reaction of N-methoxybenzamide, α-diazoester, and
alkyne was developed, providing an alternative way to
synthesize isoquinoline derivatives. Mechanistically, it is a
relay catalysis, and the reaction occurred via successive O-
alkylation and C−H activation processes, both of which were
promoted by the same catalyst.
he one-pot multicomponent reaction constitutes a class
of very important and highly attracting reactions in
either a single catalyst3a,5 or a multicatalyst system.6 However,
the relay catalysis involving C−H bond activation is still very
rare.3a,6o Its multicomponent variant is even rarer, for example,
the Cp*RhIII-catalyzed multicomponent synthesis of isoindo-
linones by Zhu et al.3a Herein we report a three-component
relay catalysis involving C−H bond activation, which is
promoted by a single rhodium(III) catalyst. In this reaction,
N-methoxybenzamide, α-diazoester,7 and alkyne are smoothly
transformed into various isoquinoline8 derivatives via succes-
sive O-alkylation and inert C−H activation processes (Scheme
1b).
T
organic chemistry owing to its high efficiency and step
economy. This field has attracted a great deal of attention
from chemists and has achieved tremendous success.1
Recently, with the boom in the area of inert C−H bond
activation,2 multicomponent reactions involving inert C−H
bond activation have been developed,3 which was pioneered by
Ellman in 2016 (Scheme 1a).3i Meanwhile, multicatalysis has
Scheme 1. Three-Component Reaction Involving C−H
Activation
Our initial studies revealed that in the presence of Cp*RhIII
catalyst, N-methoxybenzamide 1a, tert-butyl 2-diazo-2-phenyl-
acetate 2a, and diphenylacetylene 3a could undergo the three-
component reaction at room temperature, affording product
4aaa in 47% yield (Table 1, entry 1). Solvent screening
indicated that dichloromethane (DCM) was the most effective,
giving product 4aaa in 70% yield (entries 2−4). The yield
increased to 81% when the reaction time was extended to 20 h,
but no additional increment was achieved by further
prolonging the reaction time to 30 h (entries 5 and 6). An
investigation of the reaction temperature indicated that room
temperature was optimal (entries 7 and 8). For the detailed
optimization of the reaction conditions, please refer to the
Supporting Information (Tables S1−S7).
With the optimized reaction conditions in hand, we set out
to explore the substrate scope of this three-component reaction
(Figure 1). First, a series of substituted N-methoxybenzamides
were examined. The desired products 4aaa−4iaa were
obtained in good yield (62−81%). The structure of product
4baa was confirmed by single-crystal X-ray diffraction. Second,
an array of substituted α-diazoesters were investigated. The
also been emerging as a powerful strategy to achieve multistep
organic transformations in one pot.4 As one of the types of
multicatalysis, relay catalysis contains two or more mechanis-
tically different catalytic cycles, in which the product released
from the prior catalytic cycle serves as the starting material for
the succeeding catalytic cycle. In recent years, great advances
have been achieved in the field of relay catalysis,4 employing
Received: April 26, 2019
© XXXX American Chemical Society
A
DOI: 10.1021/acs.orglett.9b01456
Org. Lett. XXXX, XXX, XXX−XXX

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Letter
a
asymmetric diaryl alkyne (4-phenylphenyl) phenyl ethyne
was subjected to the reaction, two regioisomeric products 4aal
and 4aal′ were obtained in equal amounts. In contrast, when
phenyl methyl acetylene was employed, only the single
regioisomer 4aam was obtained in 74% yield. The aliphatic
alkyne but-2-yne was also attempted, giving the desired
product 4aan in 73% yield. Notably, the reaction could be
easily scaled up. As shown in Scheme 2, when 1.0 g of 1a was
subjected to the reaction, the desired product 4aaa was
obtained in 83% yield (2.71 g).
Table 1. Optimization of Reaction Conditions
b
entry
solvent
time (h)
t (°C)
yield (%)
1
2
3
4
5
6
7
8
DCE
DMF
PhCl
DCM
DCM
DCM
DCM
DCM
16
16
16
16
20
30
20
20
rt
rt
rt
rt
rt
rt
10
50
47
31
21
70
81
78
48
60
Scheme 2. Gram-Scale Reaction
a
Reaction conditions: under a nitrogen atmosphere, N-methoxyben-
zamide 1a (0.1 mmol), diazoester 2a (0.12 mmol), diphenylacetylene
3a (0.15 mmol), [Cp*RhCl2]2 (5 mol %), AgSbF6 (20 mol %), and
b
Then, preliminary mechanistic studies were carried out by
designing some control experiments. As shown in Scheme 3,
solvent (0.2 mL). Isolated yield.
Scheme 3. Control Experiments
Figure 1. Scope of substrates. All of the reactions were carried out
under a nitrogen atmosphere with 1a-i (0.10 mmol), 2b-n (0.12
mmol), 3b-n (0.15 mmol), [Cp*RhCl2]2 (5 mol %), and AgSbF6 (20
mol %) in DCM (0.2 mL) at room temperature for 20 h. Isolated
yields were reported. Purified by silica gel column chromatography
and recrystallization from petroleum ether/dichloromethane (3 mL/
0.1 mL).
two possible reaction pathways were proposed for this
reaction. The first one involves the initial reaction of N-
methoxybenzamide 1a with α-diazoester 2a to form
intermediate 5, which then reacts with 3a to form the final
product 4aaa via C−H bond activation (Scheme 3, Route 1).
The second one includes the initial reaction of N-
methoxybenzamide 1a with diphenylacetylene 3a to give
isoquinolone 7, which then reacts with α-diazoester 2a to give
the final product 4aaa (Scheme 3, Route 2). Interestingly, it
was observed that under the standard reaction conditions, N-
methoxybenzamide 1a indeed reacted well with α-diazoester
2a to form intermediate 5 in 86% yield. Isoindolone 6 was not
detected in this reaction, which was in accord with the
observations by Rovis and Yu.9 Furthermore, imidate 5 was
found to be able to smoothly react with 3a to produce the final
a
corresponding products 4aba−4aka were obtained in up to
78% yield. In addition, 2-diazo-2-phenylacetates with varied
ester groups were also tested, generating the desired products
4ala, 4ama, and 4ana in 63, 71, and 70% yield, respectively.
Finally, we investigated a variety of diaryl acetylenes bearing
either electron-withdrawing (4-F, 4-Cl, 4-Br, 4-CF3, and 2-Cl)
or electron-donating groups (4-OMe, 4-Me, 2-Me, and 4-tBu),
affording the corresponding products 4aab−4aak in good yield
(up to 80%). Besides symmetric diaryl alkynes, some
asymmetric alkynes were also investigated. When the
B
DOI: 10.1021/acs.orglett.9b01456
Org. Lett. XXXX, XXX, XXX−XXX

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Letter
product 4aaa in 70% yield. In contrast, N-methoxybenzamide
1a was found to react rather sluggishly with diphenylacetylene
3a, giving isoquinolone 7 in a low yield of 29%.10 Moreover,
isoquinolone 7 failed to react with α-diazoester 2a to give
product 4aaa under the standard reaction conditions. These
findings strongly imply that the reaction should proceed via the
proposed reaction pathway Route 1.
Scheme 4. D/H Exchange Experiment
To further confirm the validity of the proposed reaction
Route 1, the reaction was monitored by a nuclear magnetic
resonance (NMR) spectrometer in real time. Indeed, imidate 5
could be detected in the reaction mixture, and its trend of
change is shown in Figure 2. As shown in Figure 2a, the
position of the directing group was also observed for the
recovered imidate 5.
According to the above mechanistic studies, a plausible
reaction mechanism is proposed (Scheme 5). First,
Scheme 5. Proposed Reaction Mechanism
Figure 2. Reaction progress monitored by NMR spectrometer.
[Cp*RhCl2]2 reacts with AgSbF6 to produce the catalytically
active rhodium species A, which can efficiently decompose
diazoester 2a to generate carbenoid B. The attack of carbenoid
B by amide 1a gives intermediate C, which is further
transformed to imidate 5 by protonation with the concurrent
regeneration of rhodium species A. Then, the Cp*RhIII-
catalyzed C−H activation of imidate 5 occurs to generate the
five-membered cyclorhodium intermediate D. Coordination,
followed by the subsequent migratory insertion of diphenyla-
cetylene 3a into the C−Rh bond of intermediate D, affords the
seven-membered rhodacycle intermediate E. Reductive elim-
ination along with the oxidation of rhodium by the N−O bond
gives intermediate F. Lastly, the protonation and dissociation
of metal delivers the final product 4aaa together with methanol
and the recovered Cp*RhIII catalyst.
In conclusion, a rhodium-catalyzed one-pot three-compo-
nent reaction has been developed, providing an alternative way
to synthesize isoquinoline derivatives. The reaction proceeds
via a relay catalysis mechanism, involving successive O-
alkylation and C−H activation processes, both of which are
promoted by the same Cp*RhIII catalyst. Preliminary
mechanistic studies were carried out, and a plausible reaction
mechanism is depicted.
formation of imidate 5 was very fast and was completed within
10 min (71% yield). In sharp contrast, no isoquinoline product
4aaa was detected, even after 30 min, implying that this three-
component relay catalysis proceeds in a temporal separation
manner. Namely, the reaction of N-methoxybenzamide 1a and
α-diazoester 2a finished before the reaction of imidate 5 with
alkyne 3a began. From about the 40th minute, the amount of
imidate 5 started to decline along with the gradual increment
of the isoquinoline 4aaa as well as the side product methanol,
further confirming that imidate 5 was the actual reaction
intermediate (Figure 2b). Notably, the reaction of imidate 5
and alkyne 3a was much slower than the reaction of N-
methoxybenzamide 1a and α-diazoester 2a.
Subsequently, the H/D exchange experiments were
conducted. When imidate 5 was treated with D2O under the
standard reaction conditions, considerable H/D exchange on
the ortho position was observed, indicating that the C−H
bond activation process was reversible (Scheme 4, eq 1).
Moreover, when imidate 5 was allowed to react with
diphenylacetylene 3a, product 4aaa was obtained in 58%
yield with a contamination of 13% of 4aaa-d1, suggesting that
the reverse reaction of C−H activation was much slower than
the reaction step following the C−H activation (Scheme 4, eq
2). In addition, the incorporation of 60% D on the ortho
C
DOI: 10.1021/acs.orglett.9b01456
Org. Lett. XXXX, XXX, XXX−XXX

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Letter
land, 2016; p 133. (n) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.;
Zhang, Y. Org. Chem. Front. 2015, 2, 1107. (o) Zheng, C.; You, S.-L.
RSC Adv. 2014, 4, 6173. (p) Wencel-Delord, J.; Glorius, F. Nat.
Chem. 2013, 5, 369. (q) Zhu, C.; Wang, R.; Falck, J. R. Chem. - Asian
J. 2012, 7, 1502. (r) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew.
Chem., Int. Ed. 2012, 51, 8960. (s) White, M. C. Science 2012, 335,
807. (t) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(u) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F.
Angew. Chem., Int. Ed. 2012, 51, 10236. (v) Engle, K. M.; Mei, T.-S.;
Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788. (w) Yeung, C. S.;
Dong, V. M. Chem. Rev. 2011, 111, 1215. (x) Wencel-Delord, J.;
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.or-
glett.9b01456.
■
S
1
Experimental details, characterization data, and H and
13C NMR spectra (PDF)
Accession Codes
CCDC 1908915 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
data_request@ccdc.cam.ac.uk, or by contacting The Cam-
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
̈
Droge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740. (y) Sun,
C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293. (z) Li, H.; Li, B.-
J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191. (aa) Cho, S. H.; Kim, J.
Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068. (ab) Baudoin,
O. Chem. Soc. Rev. 2011, 40, 4902. (ac) Ackermann, L. Chem. Rev.
2011, 111, 1315. (ad) C−H Activation; Yu, J.-Q., Shi, Z.-J., Eds.;
Topics in Current Chemistry 292; Springer: Berlin, 2010; p 1.
(ae) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(af) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin,
O. Chem. - Eur. J. 2010, 16, 2654. (ag) Colby, D. A.; Bergman, R. G.;
Ellman, J. A. Chem. Rev. 2010, 110, 624. (ah) Balcells, D.; Clot, E.;
Eisenstein, O. Chem. Rev. 2010, 110, 749. (ai) Giri, R.; Shi, B.-F.;
Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
(aj) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42,
1074. (ak) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew.
Chem., Int. Ed. 2009, 48, 5094. (al) Bergman, R. G. Nature 2007, 446,
391.
AUTHOR INFORMATION
■
Corresponding Author
*E-mail: wangjun23@mail.sysu.edu.cn.
ORCID
Jijun Jiang: 0000-0001-9483-6033
Jun Wang: 0000-0002-4035-2786
Notes
The authors declare no competing financial interest.
(3) (a) Zhang, Y.; Zhu, H.; Huang, Y.; Hu, Q.; He, Y.; Wen, Y.; Zhu,
G. Org. Lett. 2019, 21, 1273. (b) Hoang, G. L.; Zoll, A. J.; Ellman, J.
A. Org. Lett. 2019, 21, 3886. (c) Wang, Z.; Yin, J.; Zhou, F.; Liu, Y.;
You, J. Angew. Chem., Int. Ed. 2019, 58, 254. (d) Hoang, G. L.; Streit,
A. D.; Ellman, J. A. J. Org. Chem. 2018, 83, 15347. (e) Halskov, K. S.;
Witten, M. R.; Hoang, G. L.; Mercado, B. Q.; Ellman, J. A. Org. Lett.
2018, 20, 2464. (f) Boerth, J. A.; Maity, S.; Williams, S. K.; Mercado,
B. Q.; Ellman, J. A. Nat. Catal. 2018, 1, 673. (g) Boerth, J. A.; Ellman,
J. A. Angew. Chem., Int. Ed. 2017, 56, 9976. (h) Boerth, J. A.;
Hummel, J. R.; Ellman, J. A. Angew. Chem., Int. Ed. 2016, 55, 12650.
(i) Boerth, J. A.; Ellman, J. A. Chem. Sci. 2016, 7, 1474.
ACKNOWLEDGMENTS
We thank the National Natural Science Foundation of China
(grant 21402244).
■
REFERENCES
■
(1) (a) Zhang, J.; Liang, Z.; Wang, J.; Guo, Z.; Liu, C.; Xie, M. ACS
Omega 2018, 3, 18002. (b) Wang, Y.; Lu, H.; Xu, P.-F. Acc. Chem. Res.
2015, 48, 1832. (c) Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K.
Chem. Rev. 2014, 114, 8323. (d) Cioc, R. C.; Ruijter, E.; Orru, R. V.
A. Green Chem. 2014, 16, 2958. (e) Brauch, S.; van Berkel, S. S.;
Westermann, B. Chem. Soc. Rev. 2013, 42, 4948. (f) Yu, J.; Shi, F.;
Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156. (g) Bariwal, J. B.; Trivedi,
J. C.; Van der Eycken, E. V. In Synthesis of Heterocycles via
Multicomponent Reactions II; Orru, R. V. A., Ruijter, E., Eds.; Springer:
(4) (a) Liang, Q.-J.; Xu, Y.-H.; Loh, T.-P. Org. Chem. Front. 2018, 5,
2765. (b) Skubi, K. L.; Blum, T. R.; Yoon, T. P. Chem. Rev. 2016, 116,
́
10035. (c) Afewerki, S.; Cordova, A. Chem. Rev. 2016, 116, 13512.
(d) Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.;
MacMillan, D. W. C. Science 2014, 345, 437. (e) Chen, D.-F.; Han, Z.-
Y.; Zhou, X.-L.; Gong, L.-Z. Acc. Chem. Res. 2014, 47, 2365. (f) Du,
Z.; Shao, Z. Chem. Soc. Rev. 2013, 42, 1337. (g) Allen, A. E.;
MacMillan, D. W. C. Chem. Sci. 2012, 3, 633. (h) Zhou, J. Chem. -
Asian J. 2010, 5, 422. (i) Zhong, C.; Shi, X. Eur. J. Org. Chem. 2010,
2010, 2999. (j) Shao, Z.; Zhang, H. Chem. Soc. Rev. 2009, 38, 2745.
(k) Lee, J. M.; Na, Y.; Han, H.; Chang, S. Chem. Soc. Rev. 2004, 33,
302.
́
Berlin, 2010; p 169. (h) Toure, B. B.; Hall, D. G. Chem. Rev. 2009,
109, 4439. (i) D’Souza, D. M.; Muller, T. J. J. Chem. Soc. Rev. 2007,
̈
̈
́
36, 1095. (j) Domling, A. Chem. Rev. 2006, 106, 17. (k) Ramon, D. J.;
Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602. (l) Domling, A.; Ugi, I.
̈
Angew. Chem., Int. Ed. 2000, 39, 3168.
(2) (a) Wang, W.; Lorion, M. M.; Shah, J.; Kapdi, A. R.; Ackermann,
L. Angew. Chem., Int. Ed. 2018, 57, 14700. (b) Sambiagio, C.;
(5) (a) Wu, X.; Li, X.; Huang, W.; Wang, Y.; Xu, H.; Cai, L.; Qu, J.;
Chen, Y. Org. Lett. 2019, 21, 2453. (b) Kawauchi, D.; Ueda, H.;
Tokuyama, H. Eur. J. Org. Chem. 2019, 2019, 2056. (c) Yuan, Q.;
Sigman, M. S. J. Am. Chem. Soc. 2018, 140, 6527. (d) Camp, J. E. Eur.
J. Org. Chem. 2017, 2017, 425. (e) Zhu, S.; Niljianskul, N.; Buchwald,
S. L. Nat. Chem. 2016, 8, 144. (f) Ngwerume, S.; Lewis, W.; Camp, J.
E. J. Org. Chem. 2013, 78, 920. (g) Lorion, M. M.; Gasperini, D.;
Oble, J.; Poli, G. Org. Lett. 2013, 15, 3050. (h) Li, L.; Herzon, S. B.
Nat. Chem. 2014, 6, 22. (i) Kanbayashi, N.; Takenaka, K.; Okamura,
T.-a.; Onitsuka, K. Angew. Chem., Int. Ed. 2013, 52, 4897. (j) Chen,
W.; Tay, J.-H.; Ying, J.; Sabat, M.; Yu, X.-Q.; Pu, L. Chem. Commun.
2013, 49, 170. (k) Chen, J. R.; Li, C. F.; An, X. L.; Zhang, J. J.; Zhu,
X. Y.; Xiao, W. J. Angew. Chem., Int. Ed. 2008, 47, 2489. (l) Fustero,
S.; Jimenez, D.; Sanchez-Rosello, M.; del Pozo, C. J. Am. Chem. Soc.
2007, 129, 6700. (m) Seigal, B. A.; Fajardo, C.; Snapper, M. L. J. Am.
Chem. Soc. 2005, 127, 16329. (n) Evans, P. A.; Robinson, J. E. J. Am.
Chem. Soc. 2001, 123, 4609.
̈
Schonbauer, D.; Blieck, R.; Dao-Huy, T.; Pototschnig, G.; Schaaf, P.;
Wiesinger, T.; Zia, M. F.; Wencel-Delord, J.; Besset, T.; Maes, B. U.
W.; Schnurch, M. Chem. Soc. Rev. 2018, 47, 6603. (c) Hu, Y.; Zhou,
̈
B.; Wang, C. Acc. Chem. Res. 2018, 51, 816. (d) Gandeepan, P.;
Ackermann, L. Chem. 2018, 4, 199. (e) Yoshino, T.; Matsunaga, S.
Adv. Synth. Catal. 2017, 359, 1245. (f) Ping, L.; Chung, D. S.;
Bouffard, J.; Lee, S. G. Chem. Soc. Rev. 2017, 46, 4299. (g) Ma, W.;
Gandeepan, P.; Li, J.; Ackermann, L. Org. Chem. Front. 2017, 4, 1435.
(h) Liao, K.; Pickel, T. C.; Boyarskikh, V.; Bacsa, J.; Musaev, D. G.;
Davies, H. M. L. Nature 2017, 551, 609. (i) He, J.; Wasa, M.; Chan,
K. S. L.; Shao, Q.; Yu, J.-Q. Chem. Rev. 2017, 117, 8754. (j) Crabtree,
R. H.; Lei, A. Chem. Rev. 2017, 117, 8481. (k) Gulías, M.; Mascarenas,
̃
J. L. Angew. Chem., Int. Ed. 2016, 55, 11000. (l) Gensch, T.;
Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev.
2016, 45, 2900. (m) Dailler, D.; Danoun, G.; Baudoin, O. In C−H
Bond Activation and Catalytic Functionalization II; Dixneuf, P. H.,
Doucet, H., Eds.; Springer International Publishing: Cham, Switzer-
D
DOI: 10.1021/acs.orglett.9b01456
Org. Lett. XXXX, XXX, XXX−XXX

Organic Letters
Letter
(6) (a) Zheng, H.; Wang, Y.; Xu, C.; Xiong, Q.; Lin, L.; Feng, X.
Angew. Chem., Int. Ed. 2019, 58, 5327. (b) Zhang, Q.; Wang, J.; Wei,
Y.; Zhai, H.; Li, Y. Org. Lett. 2019, 21, 1694. (c) Ge, S.; Cao, W.;
Kang, T.; Hu, B.; Zhang, H.; Su, Z.; Liu, X.; Feng, X. Angew. Chem.,
Int. Ed. 2019, 58, 4017. (d) Zhu, C.; Pinkert, T.; Gressies, S.; Glorius,
F. ACS Catal. 2018, 8, 10036. (e) Zhou, W.; Kang, J.; Cheng, K.; He,
S.; Shi, J.; Zhou, C.; Zhang, Q.; Chen, J.; Peng, L.; Chen, M.; Wang,
Y. Angew. Chem., Int. Ed. 2018, 57, 12012. (f) Zhang, D.; Lin, L.;
Yang, J.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2018, 57, 12323.
(g) Zhang, D.; Huang, Y.; Zhang, E.; Yi, R.; Chen, C.; Yu, L.; Xu, Q.
Adv. Synth. Catal. 2018, 360, 784. (h) Yang, L.-C.; Tan, Z. Y.; Rong,
Z.-Q.; Liu, R.; Wang, Y.-N.; Zhao, Y. Angew. Chem., Int. Ed. 2018, 57,
7860. (i) Yang, J.; Ke, C.; Zhang, D.; Liu, X.; Feng, X. Org. Lett. 2018,
20, 4536. (j) Wu, F.; Huang, W.; Yiliqi; Yang, J.; Gu, Y. Adv. Synth.
Catal. 2018, 360, 3318. (k) Sawant, D. M.; Sharma, S.; Pathare, R. S.;
Joshi, G.; Kalra, S.; Sukanya, S.; Maurya, A. K.; Metre, R. K.;
Agnihotri, V. K.; Khan, S.; Kumar, R.; Pardasani, R. T. Chem.
Commun. 2018, 54, 11530. (l) Rieckhoff, S.; Frey, W.; Peters, R. Eur.
J. Org. Chem. 2018, 2018, 1797. (m) Meng, J.; Fan, L.-F.; Han, Z.-Y.;
Gong, L.-Z. Chem 2018, 4, 1047. (n) Matsuda, T.; Ito, H. Org. Biomol.
Chem. 2018, 16, 6703. (o) Lu, Q.; Mondal, S.; Cembellin, S.; Glorius,
F. Angew. Chem., Int. Ed. 2018, 57, 10732. (p) Liu, Z.; Du, Q.; Zhai,
H.; Li, Y. Org. Lett. 2018, 20, 7514. (q) Li, L.-L.; Su, Y.-L.; Han, Z.-Y.;
Gong, L.-Z. Chem. - Eur. J. 2018, 24, 7626. (r) Jia, Z.-J.; Shan, G.;
Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int.
Ed. 2018, 57, 14493. (s) Huang, L.-Z.; Xuan, Z.; Jeon, H. J.; Du, Z.-
T.; Kim, J. H.; Lee, S.-g. ACS Catal. 2018, 8, 7340. (t) Hu, B.; Li, J.;
Cao, W.; Lin, Q.; Yang, J.; Lin, L.; Liu, X.; Feng, X. Adv. Synth. Catal.
2018, 360, 2831. (u) Gong, J.; Wan, Q.; Kang, Q. Adv. Synth. Catal.
2018, 360, 4031. (v) Chen, Y.; Dong, S.; Xu, X.; Liu, X.; Feng, X.
Angew. Chem., Int. Ed. 2018, 57, 16554. (w) Liu, X.; Mao, R.; Ma, C.
Org. Lett. 2017, 19, 6704. (x) Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang,
G.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2016, 55, 6075.
(y) Friedman, A. A.; Panteleev, J.; Tsoung, J.; Huynh, V.; Lautens, M.
Angew. Chem., Int. Ed. 2013, 52, 9755.
Ackermann, L. Chem. - Eur. J. 2015, 21, 15525. (p) Gupta, S.; Han, J.;
Kim, Y.; Lee, S. W.; Rhee, Y. H.; Park, J. J. Org. Chem. 2014, 79, 9094.
(q) Han, W.; Zhang, G.; Li, G.; Huang, H. Org. Lett. 2014, 16, 3532.
(r) He, R.; Huang, Z.; Zheng, Q.; Wang, C. Angew. Chem., Int. Ed.
2014, 53, 4950. (s) He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C.
Tetrahedron Lett. 2014, 55, 5705. (t) Zhao, D.; Lied, F.; Glorius, F.
Chem. Sci. 2014, 5, 2869. (u) Chinnagolla, R. K.; Pimparkar, S.;
Jeganmohan, M. Chem. Commun. 2013, 49, 3703. (v) Chuang, S. C.;
Gandeepan, P.; Cheng, C. H. Org. Lett. 2013, 15, 5750.
(w) Chinnagolla, R. K.; Pimparkar, S.; Jeganmohan, M. Org. Lett.
2012, 14, 3032. (x) Wang, H.; Grohmann, C.; Nimphius, C.; Glorius,
F. J. Am. Chem. Soc. 2012, 134, 19592. (y) Zheng, L.; Ju, J.; Bin, Y.;
Hua, R. J. Org. Chem. 2012, 77, 5794. (z) Wang, Y. F.; Toh, K. K.;
Lee, J. Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927. (aa) Wei,
X.; Zhao, M.; Du, Z.; Li, X. Org. Lett. 2011, 13, 4636. (ab) Zhang, X.;
Chen, D.; Zhao, M.; Zhao, J.; Jia, A.; Li, X. Adv. Synth. Catal. 2011,
353, 719. (ac) Too, P. C.; Wang, Y. F.; Chiba, S. Org. Lett. 2010, 12,
5688. (ad) Fukutani, T.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M.
Chem. Commun. 2009, 5141. (ae) Guimond, N.; Fagnou, K. J. Am.
Chem. Soc. 2009, 131, 12050. (af) Parthasarathy, K.; Cheng, C. H. J.
Org. Chem. 2009, 74, 9359. (ag) Korivi, R. P.; Cheng, C. H. Org. Lett.
2005, 7, 5179.
(9) (a) Lam, H.-W.; Man, K.-Y.; Chan, W.-W.; Zhou, Z.; Yu, W.-Y.
Org. Biomol. Chem. 2014, 12, 4112. (b) Hyster, T. K.; Ruhl, K. E.;
Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364.
(10) For related studies of this reaction, see: (a) Guimond, N.;
Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2011, 133, 6449.
(b) Guimond, N.; Gouliaras, C.; Fagnou, K. J. Am. Chem. Soc. 2010,
132, 6908.
(7) For reviews regarding diazo chemistry, see: (a) Xia, Y.; Qiu, D.;
Wang, J. Chem. Rev. 2017, 117, 13810. (b) Thumar, N. J.; Wei, Q. H.;
Hu, W. H. Adv. Organomet. Chem. 2016, 66, 33. (c) Liu, L.; Zhang, J.
Chem. Soc. Rev. 2016, 45, 506. (d) DeAngelis, A.; Panish, R.; Fox, J.
M. Acc. Chem. Res. 2016, 49, 115. (e) Hu, F.; Xia, Y.; Ma, C.; Zhang,
Y.; Wang, J. Chem. Commun. 2015, 51, 7986. (f) Ford, A.; Miel, H.;
Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev.
2015, 115, 9981. (g) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
(h) Xia, Y.; Zhang, Y.; Wang, J. ACS Catal. 2013, 3, 2586. (i) Doyle,
M. P.; Liu, Y.; Ratnikov, M. Org. React. 2013, 80, 1. (j) Davies, H. M.
L.; Morton, D. Chem. Soc. Rev. 2011, 40, 1857. (k) Doyle, M. P.;
Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704.
(l) Davies, H. M.; Manning, J. R. Nature 2008, 451, 417. (m) Davies,
H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
(8) For references for isoquinoline synthesis via C−H activation,
see: (a) Deshmukh, D. S.; Gangwar, N.; Bhanage, B. M. Eur. J. Org.
Chem. 2019, 2019, 2919. (b) Lin, W.; Hu, X.-X.; Zhuang, C.-W.;
Wang, Y.-Z. Tetrahedron 2019, 75, 3015. (c) Wang, Q.; Lou, J.;
Huang, Z.; Yu, Z. J. Org. Chem. 2019, 84, 2083. (d) Liu, M.; Gong,
W.; You, E.; Zhang, H.; Shi, L.; Cao, W.; Shi, J. Eur. J. Org. Chem.
2018, 2018, 4991. (e) Shi, X.; Wang, R.; Zeng, X.; Zhang, Y.; Hu, H.;
Xie, C.; Wang, M. Adv. Synth. Catal. 2018, 360, 4049. (f) Sun, J.-G.;
Zhang, X.-Y.; Yang, H.; Li, P.; Zhang, B. Eur. J. Org. Chem. 2018,
2018, 4965. (g) Webb, N. J.; Raw, S. A.; Marsden, S. P. Tetrahedron
2018, 74, 5200. (h) Wu, X. L.; Dong, L. Asian J. Org. Chem. 2018, 7,
2422. (i) Lu, Q.; Gressies, S.; Cembellin, S.; Klauck, F. J. R.; Daniliuc,
C. G.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 12778. (j) Kim, J.
H.; Greßies, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 5577.
(k) Muralirajan, K.; Kuppusamy, R.; Prakash, S.; Cheng, C.-H. Adv.
Synth. Catal. 2016, 358, 774. (l) Wang, J.; Zha, S.; Chen, K.; Zhu, J.
Org. Chem. Front. 2016, 3, 1281. (m) Zhang, S.-S.; Liu, X.-G.; Chen,
S.-Y.; Tan, D.-H.; Jiang, C.-Y.; Wu, J.-Q.; Li, Q.; Wang, H. Adv. Synth.
Catal. 2016, 358, 1705. (n) Sen, M.; Kalsi, D.; Sundararaju, B. Chem. -
Eur. J. 2015, 21, 15529. (o) Wang, H.; Koeller, J.; Liu, W.;
E
DOI: 10.1021/acs.orglett.9b01456
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