Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes

Article abstract of DOI:10.1039/d0cc02650f

A Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines instead of oxazolidines. The reaction with styrene resulted in a mixture of 2,4-diarylquinoline and 4-Arylquinoline, while only 3-Arylquinoline was formed from the reaction of epoxystyrene. This journal is

Full text of DOI:10.1039/d0cc02650f

View Article Online
View Journal
ChemComm
Chemical Communications
Accepted Manuscript
This article can be cited before page numbers have been issued, to do this please use: A. Purkait, S. Saha,
S. Ghosh and C. K. Jana, Chem. Commun., 2020, DOI: 10.1039/D0CC02650F.
Volume 54
This is an Accepted Manuscript, which has been through the
Number
January 2018
Pages 1-112
1
4
Royal Society of Chemistry peer review process and has been
accepted for publication.
ChemComm
Chemical Communications
rsc.li/chemcomm
Accepted Manuscripts are published online shortly after acceptance,
before technical editing, formatting and proof reading. Using this free
service, authors can make their results available to the community, in
citable form, before we publish the edited article. We will replace this
Accepted Manuscript with the edited and formatted Advance Article as
soon as it is available.
You can find more information about Accepted Manuscripts in the
Information for Authors.
Please note that technical editing may introduce minor changes to the
text and/or graphics, which may alter content. The journal’s standard
Terms & Conditions and the Ethical guidelines still apply. In no event
shall the Royal Society of Chemistry be held responsible for any errors
or omissions in this Accepted Manuscript or any consequences arising
from the use of any information it contains.
ISSN 1359-7345
COMMUNICATION
S. J. Connon, M. O. Senge et al.
Conformational control of nonplanar free base porphyrins:
towards bifunctional catalysts of tunable basicity
rsc.li/chemcomm

Page 1 of 5
Please doChneomt Caodmjumst margins
View Article Online
DOI: 10.1039/D0CC02650F
COMMUNICATION
Lewis Acid Catalyzed Reactivity Switch: Pseudo Three-Component
Annulation of Nitrosoarenes and (Epoxy)styrenes
Anisha Purkait, Subhajit Saha, Santanu Ghosh, and Chandan K. Jana*a
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
Lewis acid catalyzed annulation reaction via arene functionalization strong coordination with the anionic oxygen atom of the
of nitrosoarenes, and C-C cleavage of (epoxy)styrene to provide nitrone. This would open the possibility of a different mode of
arylquinolines is reported. The Lewis acid catalyst altered the reactivity of nitrone with the olefin.9 For example, the desired
annulation pattern providing arylquinolines instead of C-H functionalization of nitrosoarene could be achieved if the
oxazolidines. The reaction with styrene gave a mixture of 2,4- nitrone reacts with the styrene via a Povarov type reaction.
diarylquinoline and 4-arylquinoline, while only 3-arylquinoline was However, to the best of our knowledge, there is no report on
formed from the reaction of epoxystyrene.
the reaction of styrene or epoxystyrene with the nitrosoarene
as a three atom unit known in the literature. Herein we report
the first example of a Yb and Cu-catalyzed pseudo-three-
component annulation reaction of nitrosoarenes and styrene or
epoxystyrene providing a wide range of aryl quinolines (Scheme
1, eq 2).
Annulation reaction involving two or more components is a
powerful strategy for the synthesis of a cyclic compound.1
Multiple numbers of bond breaking and bond making are
achieved in a single operation, which makes this strategy
advantageous in the context of step and atom economy as
compared to the classical multistep reactions. Nitrosoarenes
were used in a wide variety of reactions, such as Diels-Alder,
ene, [3+2] cycloaddition, aldol reactions to install the amine and
oxygen functionality in the organic molecules.2 In addition,
nitrosoarenes also participate in different annulation reactions
to provide a variety of heterocycles.3 Primarily, the reactive
nitroso functionality of the nitrosoarenes participates in the
reactions. In most of the cases, the arene moiety is sacrificed
after the reaction. Therefore, the development of reaction for
the C-H functionalization of nitrosoarene that incorporates the
arene moiety into the product is of great interest. In this
context, a few examples of reactions of nitrosoarenes involving
both nitroso and arene moiety have been developed recently.4,5
Highly reactive molecules, such as aryne, alkyne, enone and
donor-acceptor cyclopropanes reacted with nitrosoarene acting
as three atom unit (C-C-N) in the presence of suitable metal
catalyst/reagents to provide the different heterocycles.5 In
contrast, only the nitroso functionality participates in the
reaction of nitrosoarene with styrene to provide the nitrone6
and oxazolidine derivatives (Scheme 1, eq 1).7 Nitrone, which is
well known for their 1,3-dipolar cycloaddition reaction with the
styrene/oliefin,8 formed in situ from nitrosoarene and the
styrene reacted with another equivalent of the styrene to
provide the corresponding oxazolidine derivative. We
anticipated that the use of oxophilic lanthanide-based Lewis
acid, such as Sc3+, Yb3+ could deactivate the dipole through
Scheme 1: Reactions of nitrosoarenes with styrene and epoxystyrene.
Functionalized quinoline, particularly, arylquinoline are widely
found as the key scaffold of many natural products and
bioactive molecules.10 Therefore, the efforts are being devoted
to the development of novel and more efficient synthetic
methods for the synthesis of functionalized quinoline
derivatives.11 However, the development of novel synthetic
methods to provide quinoline derivatives with wide structural
diversity starting from readily available starting materials under
simple reaction conditions still remains challenging and
desirable.
To test our hypothesis, we started our investigation by
performing a reaction of nitrone
presence of a catalytic amount of Sc(OTf)3. We were pleased to
observe that the reaction of and provided quinoline
instead of classical product, oxazolidine (eq. 3).
1 with styrene 2 in the
1
2
3
a.Department of Chemistry, Indian Institute of Technology Guwahati, India-781039
E-mail: ckjana@iitg.ac.in
† Footnotes relating to the title and/or authors should appear here.
Electronic Supplementary Information (ESI) available: [details of any supplementary
information available should be included here]. See DOI: 10.1039/x0xx00000x
Please do not adjust margins

Please do not adjust margins
ChemComm
Page 2 of 5
COMMUNICATION
Journal Name
The best reaction conditions were then used to inVvieewstAirgticaleteOntlhinee
DOI: 10.1039/D0CC02650F
substrate scope of this unprecedented annulation reaction.
First, nitrosobenzene was reacted with diversely substituted
styrene derivatives. The desired quinolines 5a-g and 5a’-g’ were
isolated with good combined yields. Styrene derivatives with
substituents at p-positions provided better yields as compared
to the substrates having m-substituents. The reaction of styrene
having a strong electron withdrawing group reacted slowly to
provide the desired quinolines with moderate yields (SI, Scheme
S1). Then the scope of the reaction using different
Then the stage was ready for testing a pseudo-three-
component reaction of nitrosoarene and styrene in the
presence of Sc(OTf)3. Accordingly, nitrosobenzene
4 was
nitrosoarenes
was
tested.
Accordingly,
substituted
reacted with styrene in the presence of 30 mol% of Sc(OTf)3 in
2
nitrosoarenes reacted smoothly with different styrene
derivatives to provide the quinoline derivatives 5h-s and 5h’-s’
with good combined yields. Interestingly, it was observed that
the quinolines which are originated from the unsubstituted
nitrones were obtained with a little lower yields as compared to
the quinolines that are formed from the substituted nitrone.
The observation can be rationalized based on the lower stability
of the unsubstituted nitrones as compared to its substituted
analogs.12
refluxing toluene for 24 h. As expected, the 2,4-diarylquinoline
5b and 4-arylquinoline 5b’ were isolated as 3:1 ratio with a 47%
combined yield (SI, Table S1). The best yield of the desired
quinoline was observed when the reaction with reduced
catalyst loading was carried out in refluxing DCE instead of
refluxing toluene (entry 6).
The reaction of substrate 6 having two styrene moiety was then
investigated. Both mono-substituted 7b and 2,4-disubstituted
7a quinolines were formed under standard conditions (eq 4).
Quinoline 7a derivative having two styrene units can serve as
the potential crosslinking agent in polystyrene synthesis. The
reactions
with
α-methylstyrene,
stilbene
and
1-
phenylbutadiene did not provide the desired quinolines
(Scheme S2). Interestingly, the reaction of β-methylstyrene and
nitrosobenzene under standard conditions provided 2-phenyl
quinoline via a different reaction pathway (eq 5, Scheme S2).
Subsequently, we explored the possibility of the annulation
reaction of nitrosobenzene with epoxy-styrene. Therefore,
nitrosobenzene was reacted with styrene oxide in place
styrene. Interestingly, only 3-phenyl quinoline was isolated with
53% yield. This interesting observation led us to investigate the
reaction further. Various reaction conditions were screened to
maximize the yield of 3-phenyl quinoline (Table S2). Sc(OTf)3
was found to be the best catalyst for this reaction in refluxing
dichloroethane. However, a similar result was obtained when
Cu(OTf)2 was used as the catalyst under the same conditions.
Optimized conditions using cost-effective catalyst Cu(OTf)2 was
used to study the substrate scope of the reaction. Differently
substituted styrene oxides were reacted with various
Scheme 2: Scope of annulation reaction of nitrosoarenes and styrenes.
2 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 3 of 5
ChemComm
Please do not adjust margins
Journal Name
COMMUNICATION
nitrosoarene to obtain a series of structurally diverse 3-aryl CuII. C-C bond cleavage of the resulting ionic intermediate 18
View Article Online
quinolines 9a-o with good yields (Scheme 3). Substrates occurred to provide the nitrone 12 and aDldOeI:h1y0d.1e03199/D. T0ChCe0m26e5t0aFl
containing both the electron-donating and electron- coordinated nitrone 12 reacted with the enolate 21, which was
withdrawing groups provided the desired quinolines with good generated in situ from styrene oxide
8 via Meinwald
yields. The reaction of 4-oxiranylpyridine did not provide the rearrangement,15 either via a concerted or stepwise pathway
desired quinoline. However, alkyl epoxide participated in the involving Friedel-Crafts reaction (Scheme S5) to provide the N-
reaction to provide 3-alkylquinoline 9p
.
oxide 20. A reaction of pre-formed nitrone 10 with aldehyde 17
which is capable of generating enolate related to 21, producing
desired quinolines (9a 9q) supports the intermediacy of 21 in
,
,
the reaction. Fast aromatization followed by dehydration
yielded observed 3-aryl quinoline as the single regioisomer.
Scheme 3: Scope of the reaction of nitrosoarenes and styrene oxide derivatives.
On the basis of our experimental results and literature reports,
a plausible mechanism for the formal [3+2+1] annulation of
nitrosoarene and styrene is depicted in Scheme 4a. The nitrones
1 (11) and 10 (12) were formed from the reaction of
nitrosoarene and styrene involving azodioxy dimer A113 and
diazetidine derivative D114 (Scheme S4, see SI).6 The nitrones
could also be formed from nitrosoarene 4 and styrene following
a radical pathway.6,7 Both the metal coordinated nitrone
derivatives 11 and 12 reacted with another equivalent of
styrene through the Povarov type reaction to provide the
tetrahydroquinoline derivatives 14 and 13
, respectively.
Aromatization and dehydration of 14 and 13 produced
respective dihydroquinoline 16 and 15, which upon oxidation in
the presence of oxygen or nitrosoarene provided the observed
aryl quinolines
To understand the mechanism of annulation reaction of epoxy
styrene and nitrosoarene, epoxy styrene was reacted with
5 and 5’.
Scheme 4: Controlled experiments and proposed reaction mechanism.
8
In summary, we have developed an unprecedented annulation
reaction of nitrosoarenes and epoxy(styrene) providing
arylquinolines with wide structural diversity. The cleavage
across C=C of styrene and epoxide of epoxystyrene provided the
nitrone intermediate. The use of the Lewis acid catalyst
switched the reaction of nitrone and styrene from [3+2] to [4+2]
cycloaddition and thus allowed to form quinoline derivatives
instead of oxazolidines. The nitrones reacted with styrene to
give a mixture of 2,4-diarylquinoline and 4-arylquinoline. On the
other hand, 3-arylquinoline was formed selectively from the
reaction of epoxystyrene via cycloaddition of nitrone and
pre-formed nitrone 10 from nitroarene and formaldehyde
(Scheme 4, eq 5). Under standard conditions, the 3-aryl
quinoline 9a was isolated with 73 % yield. This indicates the
intermediacy of nitrone 10 in the annulation reaction of epoxy
styrene and nitrosoarene. Moreover, the formation of aryl
aldehyde (19) corresponding to the styrene oxide was observed
in the reaction (Scheme S3). Based on these results, a plausible
reaction mechanism has been depicted in Scheme 4c.
Nucleophilic nitrosoarene
4 added to the least hindered site of
styrene oxide 8, which is activated by the coordination with the
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
Please do not adjust margins

Please do not adjust margins
ChemComm
Page 4 of 5
COMMUNICATION
Journal Name
55, 13590; (i) J. B. Shaum, D. J. Fisher, M. M. Sroda, L. Limona
enol/metal-enolate derived from epoxystyrene through
Meinwald rearrangement.
We acknowledge Science and Engineering Research Board
(SERB), New Delhi (CRG/2019/000330) for funding.
View Article Online
and J. R. de Alaniz, Chem. Sci., 2018, 9,D8O7I:4180..1039/D0CC02650F
(a) A. van der Werf and N. Selander, Org. Lett., 2015, 17, 6210;
(b) C. K. Ingold, J. Chem. Soc., Trans., 1925, 127, 513; (c) P. W.
Robertson, T. R. Hitchings and G. M. Will, J. Chem. Soc.,1950,
808; (d) R. J. Sundberg, R. H. Smith and J. E. Bloor, J. Am. Chem.
Soc., 1969, 91, 3392; (e) S. K. Roy, A. Purkait, S. M. T. Aziz and
C. K. Jana, Chem. Commun., 2020, 56, 3167
4
5
Conflicts of interest
“There are no conflicts to declare”.
(a) A. Penoni, J. Volkman and K. M. Nicholas, Org. Lett., 2002,
4
, 699; (b) A. Penoni, G. Palmisano, Y. -L. Zhao, K. N. Houk, J.
Volkman and K. M. Nicholas, J. Am. Chem. Soc., 2009, 131
,
653; (c) S. Murru, A. A. Gallo and R. S. Srivastava, Eur. J. Org.
Chem., 2011, 2035; (d) S. Murru, A. A. Gallo and R. S.
Notes and references
‡ Footnotes relating to the main text should appear here.
Srivastava, ACS Catal., 2011,
1, 29; (e) S. Chakrabarty, I.
Chatterjee, L. Tebben and A. Studer, Angew. Chem., Int. Ed.,
2013, 52, 2968; (f) S. Das, S. Chakrabarty, C.G. Daniliuc and A.
Studer, Org. Lett., 2016, 18, 2784; (g) S. Das, C. G. Daniliuc and
A. Studer, Org. Lett., 2016, 18, 5576; (h) A. Purkait, S. K. Roy,
H. K. Srivastava and C. K Jana, Org. Lett., 2017, 19, 2540; (i) L.
1
For selected reviews see; (a) D. Mal and P. Pahari, Chem. Rev.,
2007, 107, 1892; (b) R. Narayan, M. Potowski, Z. J. Jia, A. P.
Antonchick and H. Wadmann, Acc. Chem. Res., 2014, 47
,
1296; (c) M. E. Jung, Tetrahedron, 1976, 32, 3; (d) A. Moyano
and R. Rios, Chem. Rev., 2011, 111, 4703; (e) G. Dominguez
and J. Perez-Castells, Chem. Soc. Rev., 2011, 40, 3430; (f) B.
Alcaide, P. Almendros and C. Aragoncillo, Chem. Soc. Rev.,
2010, 39, 783; (g) Y. Wang, H. Lu, P.-F. Xu, Acc. Chem. Res.
2015, 48, 1832; for selected report; (h) S. M. B. Maezono, S.
H. Kim and Y. R. Lee, Org. Chem. Front., 2018,
Davies, J. -F. Marcoux and P. J. Reider, Org. Lett., 2001,
(j) X. Xu, X. Xu, P.Y. Zavalij and M. P. Doyle, Chem. Commun.,
2013, 49, 2762; (k) K. B. Manjappa, Y.-T. Peng, T. -J. Liou and
D. -Y. Yang, RSC Adv., 2017, 7, 45269; (l) X. -F. Mao, X. -P. Zhu,
Yang, B. Tan, F. Wang and G. Zhong, J. Org. Chem., 2009, 74
1744; (j) Z. -X. Sun and Y. Cheng, Org. Biomol. Chem., 2012, 10
,
,
4088; (k) P. Sharma and R. S. Liu, Org. Lett., 2016, 18, 412; (l)
Y. Yang, H. X. Ren, F. Chen, Z. B. Zhang, Y. Zou, C. Chen, X. J.
Song, F. Tian, L. Peng and L. X. Wang, Org. Lett., 2017, 19
,
5
, 3368; (i) I. W.
, 209;
2805; (m) W. Hu, Q. Zheng, S. Sun and J. Cheng, Chem.
Commun., 2017, 53, 6263; (n) S. Qiu, R. Liang, Y. Wang and S.
Zhu, Org. Lett., 2019, 21, 2126; (o) Y. Xiao, X. Wu, H. Wang, S.
Sun, J.-T. Yu and J. Cheng, Org. Lett., 2019, 21, 2565.
(a) C. K. Ingold and D. Weaver, J. Chem. Soc., 1924, 125, 1456;
(b) N. F. Hepfinger and C. E. Griffin, Tetrahedron Lett., 1963,
3
6
D. -Y. Li and P. -N. Liu, J. Org. Chem., 2017, 82, 7032.
2
Selected reviews see, (a) H. Waldmann, Synthesis, 1994, 535;
(b) W. Adam and O. Krebs, Chem. Rev., 2003, 103, 4131; (c) B.
4
, 1361.
7
8
J. Y. Kang, A. Bugarin and B. T. Connell, Chem. Commun., 2008,
S. Bodnar and M. J. Miller, Angew. Chem., Int. Ed., 2011, 50
,
3522.
5630; (d) L. I. Palmer, C. P. Frazier and J. R. de Alaniz, Synthesis,
2014, 269; (e) H. Yamamoto and N. Momiyama, Chem.
Commun., 2005, 3514; (f) J. Huang, Z. Chen, J. Yuan and Y.
(a) T. Hashimoto and K. Maruoka, Chem. Rev., 2015, 115
,
5366; (b) K.V. Gothelf and K. A. Jørgensen, Chem. Rev., 1998,
98, 863; (c) L. Zheng, F. Gao, C. Yang, G, -L, Gao, Y. Zhao, Y.
Gao and W. Xia, Org. Lett., 2017, 19, 5086.
(a) P. Merino, T. Tejero, I. Delsoc and R. Matuted, Org. Biomol.
Chem., 2017,15, 3364; (b) L. R. Domingo, Eur. J. Org. Chem.,
2000, 2265; (c) P. Merino and T. Tejero, Tetrahedron, 2001,
57, 8125.
Peng, Asian J. Org. Chem., 2016,
5, 951; Selected recent
reports: (g) J. Seayad, P. K. Patra, Y. Zhang and J. Y. Ying, Org.
Lett., 2008, 10, 953; (h) D. J. Fisher, G. L. Burnett, R. Velasco
and J. R. de Alaniz, J. Am. Chem. Soc., 2015, 137, 11614; (i) V.
Dhayalan, C. Sämann and P. Knochel, Chem. Commun., 2015,
51, 3239; (j) I. Ramakrishna, H. Sahoo and M. Baidya, Chem.
Commun., 2016, 52, 3215; (k) P. Sharma and R. -S. Liu, Chem.
Eur. J., 2016, 22, 15881; (l) Y. Hayashi, J. Yamaguchi, T. Sumiya
and M. Shoji, Angew. Chem., Int. Ed., 2004, 43, 1112; (m) S. K.
Roy, A. Tiwari, M. Saleem and C. K. Jana, Chem. Commun.,
2018, 54, 14081; (n) C. K. Jana and A. Studer, Angew. Chem.,
Int. Ed., 2007, 46, 6542; (o) C. K. Jana, S. Grimme and A.
Studer, Chem. Eur. J. 2009, 15, 9078; (p) D. Atkinson, M. A.
Kabeshov, M. Edgar and A. V. Malkov, Adv. Synth. Catal.,
2011, 353, 3347; (q) B. Maji and H. Yamamoto, J. Am. Chem.
Soc., 2015, 137, 15957; (r) A. P. Chavannavar, A. G. Oliver and
B. L. Ashfeld, Chem. Commun., 2014, 50, 10853; (s) R. K. R.
Singha and R. -S. Liu, Chem. Commun., 2014, 50, 15864; (t) J.
Feng, P.-J. Ma, Y.-M. Zeng, Y.-J. Xub and C. -D. Lu, Chem.
Commun., 2018, 54, 2882; (u) J. Liu, M. Skaria, P. Sharma, Y. -
9
10 (a) J. P. Michael, Nat. Prod. Rep., 2008, 25, 166; (b) J. P.
Michael, Nat. Prod. Rep., 2001, 18, 543.
11 Selected relevant reports see: (a) J. Liu, F. Liu, Y. Zhu, X. Ma
and X. Jia, Org. Lett., 2015, 17, 1409; (b) Y. Li, X. Cao, Y. Liu and
J. -P. Wan, Org. Biomol. Chem., 2017, 15, 9585; (c) Y. Zhang,
M. Wang, P. Li and L. Wang, Org. Lett., 2012, 14, 2206; (d) R.
Deshidi, S. Devaria and B. A. Shah, Org. Chem. Front., 2015, 2,
515; (e) W. Ahmed, S. Zhang, X. Yu, Y. Yamamoto and M. Bao,
Green Chem., 2018, 20, 261; (f) M. Zhong, S. Sun, J. Cheng and
Y. Shao, J. Org. Chem., 2016, 81, 10825; (g) Y. Liu, C. Wang, N.
Lv, Z. Liu and Y. Zhanga, Adv. Synth. Catal., 2017, 359, 1351;
(h) W. Jiang, Y. Wang, P. Niu, Z. Quan, Y. Su and C. Huo, Org.
Lett., 2018, 20, 4649; (i) J. Cen, J. Li, Y. Zhang, Z. Zhu, S. Yang
and H. Jiang, Org. Lett., 2018, 20, 4434; (j) S. Das, D. Maiti and
S. De Sarkar, J. Org. Chem. 2018, 83, 2309. (k) H. Jiang, X. An,
K. Tong, T. Zheng, Y. Zhang, S. Yu, Angew. Chem. Int. Ed. 2015,
54, 4055.
W. Chiang and R. -S. Liu, Chem. Sci., 2017, 8, 5482.
3
(a) N. Vemula, A. C. Stevens, T. B. Schon and B. L. Pagenkopf,
Chem. Commun., 2014, 50, 1668; (b) N. Vemula and B. L.
Pagenkopf, Eur. J. Org. Chem., 2015, 4900; (c) T. Chidley, N.
Vemula, C. A. Carson, M. A. Kerr and B. L. Pagenkopf, Org.
Lett., 2016, 18, 2922; (d) R. K. Kawade and R. S. Liu, Angew.
Chem., Int. Ed., 2017, 129, 2067; (e) C. -H. Chen, Y. -C. Tsai and
R. -S. Liu, Angew. Chem., Int. Ed., 2013, 52, 4599; (f) S. Manna,
R. Narayan, C. Golz, C. Strohmann and A. P. Antonchick,
Chem.Comm., 2015, 51, 6119; (g) X. Lv, Z. Kang, D. Xing and
W. Hu, Org. Lett., 2018, 20, 4843; (h) S. Ghosh, G. Kumar,
Naveen, S. Pradhan and I. Chatterjee, Chem. Commun., 2019,
12 E. J. Fornefeld and A. J. Pike, J. Org. Chem., 1979, 44, 835.
13 D. Beaudoin and J. D. Wuest, Chem. Rev., 2016, 116, 258.
14 (a) P. Singh, D. G. B. Boocock and E. F. Ullman, Tetrahedron
Lett., 1971, 12, 3935; (b) R. W. Hoffmann and H. Häuser,
Angew. Chem., 1964, 76, 346; (c) J. Firl and S. Sommer,
Tetrahedron Lett., 1969, 10, 1133; (d) A. I. Meyers, J. Org.
Chem., 1961, 26, 218.
15 (a) M. W. C. Robinson, K. S. Pillinger and A. E. Graham,
Tetrahedron Lett., 2006, 47, 5919; (b) A. K. Pandey, R. K.
Varshnaya and P. Banerjee, Eur. J. Org. Chem., 2017, 1647.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins

Page 5 of 5
ChemComm
Please do not adjust margins
Journal Name
COMMUNICATION
View Article Online
DOI: 10.1039/D0CC02650F
TOC: Lewis acid alters the annulation pattern to
construct arylquinolines via C-H functionalization of
nitrosoarenes, and C-C cleavage of (epoxy)styrene.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins