From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization

Article abstract of DOI:10.1002/chem.201703218

Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.

Full text of DOI:10.1002/chem.201703218

A Journal of
Accepted Article
Title: From Anilines to Quinolines: Iodide and Silver-Mediated Aerobic
C-H/C-H Oxidative Annulation/Aromatization
Authors: Jiwei Wu, Zhixiong Liao, Dong Liu, Chien-Wei Chiang, Zheng
Li, Zhonghao Zhou, Hong Yi, Xu Zhang, Zixin Deng, and
Aiwen Lei
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To be cited as: Chem. Eur. J. 10.1002/chem.201703218
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From Anilines to Quinolines: Iodide and Silver-Mediated Aerobic
C-H/C-H Oxidative Annulation/Aromatization
Jiwei Wu+,[a] Zhixiong Liao+,[a],[b] Dong Liu,[a] Chien-Wei Chiang,[a] Zheng Li,[a] Zhonghao Zhou,[a] Hong
Yi,[a] Xu Zhang,[a] Zixin Deng,*[b] and Aiwen Lei*[a],[b]
Abstract: Quinolines synthesis from easily accessible raw materials,
such as anilines, is valuable and meaningful task. Herein, we
communicate an iodide and silver-mediated C-H/C-H oxidative
annulation/aromatization between anilines and allyl alcohols. This
protocol provides a direct route to the synthesis of quinolines
derivatives from inexpensive commodities. Various kinds of anilines,
even heterocyclic anilines, were shown to be workable substrates,
generating the corresponding multi-substituted quinolines in good
yields.
converting maximum atoms from the substrates into the target
molecules, or developing a general way to synthesize quinolines
with diverse substituents, etc.[15] Moreover, if transition-metal
free conditions were introduced, it could avoid metal residual in
the final product, which was more attractive but also challenging.
Recently, iodine-catalyzed oxidative coupling reactions are
undergoing blow-out advancements, which effectively avoid the
problem of metal residual and show excellent catalytic activity.[16]
Herein, we would like to communicate a direct method to
synthesize quinolines from easily accessible materials (anilines
and allyl alcohols) under iodide or iodide and silver-mediated
conditions.
Among the myriad ring-forming reactions in heterocycle
synthesis, the oxidative coupling/annulations of alkenes or
alkynes with aryl substrates bearing various heterotom-
containing functional groups is
a uniquely straightforward
method and one of the most promising strategies.[1] During the
last decade, a number of aryl substrates (like phenols,[2] benzoic
acids,[3] benzyl alcohols,[4] thiophenols,[5] aryphosphine oxides,[6]
nitrogen substituted anilines,[7] benzamides,[8] benzylamines,[9]
arylimines[10] and others[11] etc.) have been reported to conduct
oxidative annulations with alkenes or alkynes to synthesize
various kinds of heterocycles (like benzofurans, isocoumarins,
isochromenes, benzothiophenes, benzo[b]phosphole-oxides,
indoles, isoquinolones, isoquinolines etc.) under transition-metal
catalysis such as Rh, Ru, Pd, etc. However, in spite of such
achievements accomplished, protocols of direct oxidative
coupling/annulations between primary anilines with carbon-
carbon multiple bonds for the synthesis of heterocycles are still
rare and of great challenge,[12] which might be partially due to
the easily oxidized characteristic and strong coordination of
primary anilines.
Scheme 1. Reaction design of the oxidative coupling between anilines and
allyl alcohols for the synthesis of quinolines.
As a continous interest in heterocycles synthesis via oxidative
couplings in our group, we chose commercially available and
sixpenny anilines (C-C-N unit) to start our research to construct
quinolines nucleus. Then
a C-C-C unit was needed by
retrosynthetic analysis. Allyl alcohol, as a simple and easily
accessible chemical material, was an idea coupling partner.
Thus, an oxidative annulation/aromatization between simple
anilines and allyl alcohols for the synthesis of quinolines was
designed (scheme 1). From the view of efficiency of bond
formation and economy of raw material, this protocol represents
one of the most attractive strategies towards quinolines. Hence,
we document our recent progress on this topic.
Quinoline derivatives represent a significant and common
heterocyclic compounds, which widely exist in numerous natural
products, pharmaceuticals and agrochemicals.[13] Until now,
innumerable methods have been utilized for the construction of
quinoline skeletons.[14] However, challenges still existed, such as
using commercially available or readily accessible materials,
Initially, we chose 2-chloro-4-methylaniline (1a) and allyl
alcohol (2a) as the model substrates to launch oxidative cross-
coupling. Selected results are listed in Table 1. Gratifyingly, the
oxidative coupling/cyclization reaction proceeded smoothly to
afford the desired quinoline product in 56% yield by using
[a]
J. Wu, Z. Liao, D. Liu, C.-W. Chiang, Z. Li, Z. Zhou, H. Yi, X. Zhang,
Prof. Dr. Z. Deng, Prof. Dr. A. Lei
o
The Institute for Advanced Studies (IAS), college of Chemistry and
Molecular Sciences, Wuhan University
Wuhan 430072 Hubei (P.R.China)
K2S2O8 as the oxidant with KI as the effective additive at 120 C
in DMA for 12 h under O2 atmosphere (Table 1, entry 1). When
Ag2CO3 was added in this reaction, the yield of 3a improved to
63% (Table 1, entry 2). Through an investigation of different
silver salts, we found that Ag2CO3 was still the best choice for
this reaction (Table 1, entries 3 and 4). Extensive oxidants
E-mail: aiwenlei@whu.edu.cn; zxdeng@whu.edu.cn
Z. Liao, Prof. Dr. Z. Deng, Prof. Dr. A. Lei
Key Laboratory of Combinatorial Biosynthesis and Drug Discovery
(Wuhan University), Ministry of Education Wuhan University School
of Pharmaceutical Sciences,
[b]
[+]
2-
screening showed that S2O8 played a critical role in this
Wuhan 430072 Hubei (P.R.China)
These authors contributed equally to this work
transformation (Table 1, entries 5-10 and 20). Na2S2O8 and
(NH4)2S2O8 were inferior to K2S2O8. While DDQ and DTBP
revealed no reaction efficiency as well as in the absence of
K2S2O8. Notably, in the presence of hypervalent iodine reagent,
Supporting information for this article is given via a link at the end of
the document.
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Table 1. Impact of reaction parameters on the oxidative coupling
between 1a and 2a.[a]
Table 2. Substrate scope for oxidative coupling between anilines
and allyl alcohols for the synthesis of quinolines.
Reaction conditions: [a] 1 (0.5 mmol), 2a (1.0 mL), Ag2CO3 (2 mol%) KI (0.5
mmol), K2S2O8 (1 mmol) in 2.0 mL DEF at 120 oC under O2 for 12 h. Yields
presented were of isolated products. [b] 1 (0.5 mmol), 2a (1.0 mL), KI (0.4
mmol), K2S2O8 (0.8 mmol) in 2.0 mL DMA at 120 oC under O2 for 12 h.
[a] Unless otherwise noted, the reaction was carried out with 1a (0.5 mmol), 2a
(1.0 mL), [Ag] (2 mol%), RI (0.4 mmol), [O] (0.8 mmol) in 2.0 mL [Sol.] at 120
oC under O2 for 12 h. [b] Yields shown are of isolated products. [c] 100 oC. [d]
KI 1 equiv. [e] KI 1.5 equiv. [f] K2S2O8 2 equiv. [g] K2S2O8 3 equiv. n.d. = not
detected. DDQ = 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone. DTBP = Di-tert-
butylperoxide. DEF = N,N-Diethylformamide.
experiment demonstrated that KI additive significantly promoted
this transformation since a poor yield was obtained in the
absence of KI (20% vs 70%, Table 1, entries 16 and 17). When
the amount of KI increased to 1 equivalent, the yield of 3a
improved to 73% (entery 18). It is noteworthy that increasing the
amount of K2S2O8 to 2 equivalent afforded an improved yield of
80% (Table 1, entry 21).
PhI(OAc)2, no desired quinoline product was detected while
molecular iodine gave an inferior result to K2S2O8. Other iodine
n
sources such as Bu4NI were inferior to KI (Table 1, entry 11).
Further optimization showed that reaction temperature also
distinctly influenced the reaction efficiency, since a sharply
decreased yield was obtained at 100 oC (Table 1, entry 12).
However, solvent effect showed that DEF is a superior choice
than DMA, DMF, DMSO and NMP, which increased the yield of
the desired product to 70% (Table 1, entries 13-16). A control
With the optimal reaction conditions established, reactions of
various substituted anilines (1) combined with allyl alcohol (2a)
were explored and results are summarized in table 2. Initially,
we tested the reactivity of 2,4-disubstituted anilines. Notably,
anilines bearing all the halogen substituents from F to I (3b to 3i)
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could all be well tolerated in this reaction, generating the
corresponding halogenated quinolines in moderate to good
yields, which allows for further functionalization of this type of
heterocyclic cores. 2,3-Disubstituted anilines, the substituent
including NO2 (3j) and Cl (3k) could be well tolerated in this
method and the yields of desired products are up to 72%. For
2,5-disubstituted anilines, reactions also proceeded smoothly
with allyl alcohol to deliver the desired products in good yields, in
which F (3m), Cl (3o), Br (3l) even NO2 (3n) groups could be
well tolerated. 3,5-Dimethylaniline could be well transformed into
the desired quinoline (3x) in 70% yield. Then we turned our
attention to mono-substituted anilines. The results revealed that
anilines with ortho substituents such as OPh (3p), Ph (3q) or I
(3r) could be well tolerated. p-COOEt and p-Ph-substituted
anilines could also cross-couple smoothly with allyl alcohol to
generate the desired quinoline derivatives (3s and 3t) in
moderate yields. Notably, biaryl substituted anilines (3u-3w)
proved to be good substrates. In addition, 2,4,5-trisubstituted
aniline (3y) or 2,3,4-trisubstituted aniline (3z) could also be well
tolerated. Benzo[h]quinolone (3aa) could be constructed by
using simple naphthalen-1-amine combined with allyl alcohol in
this protocol. Notably, heterocyclicaniline, 6-methylpyridin-2-
amine (3ab) and isoquinolin-5-amine (3ac) were shown to be
good coupling partners with allyl alcohol, smoothly delivering the
desired heteroquinolines, albeit in low yields.
Scheme 3. Control experiments.
Furthermore, in order to gain more mechanistic understanding
of this reaction, control experiments (Scheme 3 and Scheme S1)
were carried out. Initially, allyl amines were supposed to be
generated from anilines and allyl alcohols, and considered to be
the real reaction intermediates. Thus N-allyl-2-methyl-3-
nitroaniline (4) was synthesized and put into the reaction system
under standard conditions (Scheme 3， eq. 1). However, the
desired quinoline product was isolated in only 37% yield with
Ag2CO3 and 27% without Ag2CO3, which indicated that allyl
amine was possibly not the active intermediate of this reaction
and the role of Ag2CO3 may just promote 4 to form 3a. On the
other hand, allyl alcohol was believed to be easily oxidized to
allyl aldehyde (5), which could possibly react with aniline to
generate imine intermediate. Therefore, reaction of aniline with
allyl aldehyde was further carried out (Scheme 3， eq. 2). While
no desired product was observed, thus implying that imine was
also probably not the reaction intermediate. Meanwhile, radical-
trapping experiment was conducted to clarify whether this
reaction involved radical process. When 2 equiv of BHT (2,6-di-
tert-butyl-4-methylphenol) was added into the reaction system,
the desired product could still be obtained in 77% yield (Scheme
3， eq. 3), thus suggesting that radical process was probably
not involved in this reaction.
Then different allyl alcohols were explored in above optimal
reaction conditions, unfortunately, with very low reactivity.
Through an investigation of different reaction conditions, we
delight to found that 2-chloro-4-methylaniline (1a) reacted with 2-
methylprop-2-en-1-ol (2b) efficiently by using 1 equivalent KI
and 2 equivalent of K2S2O8 at 120 oC in DMSO for 12 h under O2
atmosphere, giving the desired product in 75% yield.
Interestingly, 3ae was obtained when 2-buten-1-ol (2c) was
used in this reaction and the structure of 3ae was proved by X-
ray single crystal diffractometer (Scheme 2).
The experimental results of the combination of KI/ I2/ O2 and
the absence of KI (Table 1, entries 10 and 17) indicated that
some undefined iodine species was involved and played a
critical role in this transformation. According to the previous
reports[17] and above results, a proposed mechanism is depicted
in Scheme 4. Firstly, electrophilic attack of iodine species on the
unsaturated bond of 2a affords three membered ring of iodonium
A, followed by nucleophilic attack of aniline to afford B. Then,
proton elimination of B generates intermediate C. Subsequently,
intramolecular nucleophilic substitution of C delivers an oxonium
cation
D along with the release of iodide anion. Later,
intramolecular nucleophilic attack of D affords E, followed by
proton elimination to generate F. Finally, F was oxidized by
K2S2O8 and O2 to give the desired quinolines. In path B, the
intermediate 4 was formed from oxidation dehydration of aniline
and 2a. Then unsaturated bond of 4 was attacked by iodine
species to form an iodonium intermediate G. Finally, silver
promoted transformation of G to desired product 3.
Scheme 2. Substrate scope for oxidative coupling between 1a and allyl
alcohols for the synthesis of quinolines.
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10.1002/chem.201703218
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This work was supported by the National Natural Science
Foundation of China (21390400, 21520102003, 21272180,
21302148), the Hubei Province Natural Science Foundation of
China (2013CFA081), the Research Fund for the Doctoral
Program of Higher Education of China (20120141130002), and
the Ministry of Science and Technology of China
(2012YQ120060). The Program of Introducing Talents of
Discipline to Universities of China (111 Program) is also
appreciated.
Keywords: Quinolines • iodide • silver • oxidative annulation •
aromatization
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In conclusion, we have communicated an iodide and silver-
mediated C-H/C-H oxidative annulation/aromatization for the
synthesis of multisubstituted quinolines from simple primary
anilines and allyl alcohols. Different substituted quinolines could
be synthesized in good yields from the corresponding anilines
and allyl alcohols. Mechanistic studies showed that radical
process was unlikely to be involved in this transformation, and
some uncertain iodine species was possibly the active reaction
species
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Experimental Section
Method A: Ag2CO3 (2.8 mg, 2 mol%), K2S2O8 (270.3 mg, 1 mmol), 1 (0.5
mmol) and KI (83.0 mg, 0.5 mmol) were added to a 25 mL dried schlenk
tube equipped with a magnetic stirred bar. A balloon filled with O2 (1 atm)
was connected to the Schlenk tube through the side arm, and DEF (2
mL), 2 (1 mL) were then injected into the tube by syringe. The reaction
was then heated to 120 oC and stirred for 12 h. After completion of the
reaction, the mixture was quenched and neutralized by NaHCO3
aqueous solution. The solution was extracted with ethyl acetate. The
organic layers were combined and dried over sodium sulfate. After
concentrated under vacuum, the residue was then purified by flash
chromatography on silica gel with a mixed eluent of petroleum and ethyl
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10.1002/chem.201703218
Chemistry - A European Journal
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Text for Table of Contents
Jiwei Wu, Zhixiong Liao, Dong Liu,
Chien-Wei Chiang, Zheng Li, Zhonghao
Zhou, Hong Yi, Xu Zhang, Zixin Deng,*
and Aiwen Lei*
Page No. – Page No.
From Anilines to Quinolines: Iodide
and Silver-Mediated Aerobic C-H/C-H
Oxidative Annulation/Aromatization
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