Straightforward synthesis of quinolines from enones and 2-aminobenzyl alcohols using an iridium-catalyzed transfer hydrogenative strategy

Article abstract of DOI:10.1039/c8ob01321g

A new protocol for the direct synthesis of quinolines from enones and 2-aminobenzyl alcohols via iridium-catalyzed transfer hydrogenative reactions has been demonstrated. This method employs easily available [IrCp?Cl₂]₂/t-BuOK as the efficient catalyst system, proceeding with the merits of high step- and atom efficiency, mild reaction conditions and operational simplicity. The experimental studies suggest that the reactions start with transfer hydrogenation, followed by the Friedl?nder reaction to give the final products.

Full text of DOI:10.1039/c8ob01321g

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Takeharu Haino et al.
Solvent-induced emission of organogels based on tris(phenylisoxazolyl)
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Straightforward Synthesis of Quinolines from Enones and 2-
Aminobenzyl Alcohols Using an Iridium-Catalyzed Transfer
Hydrogenative Strategy
Received 00th January 20xx,
Accepted 00th January 20xx
Biao Xiong*, Yingying Wang, Yuan Liu, Yandan Bao, Zhaoguo Liu, Yanan Zhang and Yong Ling*
DOI: 10.1039/x0xx00000x
www.rsc.org/
A new protocol for the direct synthesis of quinolines from enones and 2-aminobenzyl alcohols via iridium-catalyzed
transfer hydrogenative reactions has been demonstrated. This method employs easily available [IrCp*Cl2]2/t-BuOK as the
efficient catalyst system, proceeding with the merits of high step- and atom efficiency, mild reaction conditions and
operational simplicity. The experimental studies suggest that the reactions start with the transfer hydragenation, followed
by
Friedländer
reaction
to
give
the
final
products.
functionalized products. Generally, these methods abstract
hydrogen from alcohols and transfer it to unsaturated bonds
of starting coupling reagents, intermediate products or
additional sacrificial hydrogen acceptors (SHAs). To date, a
plenty of protocols of metal-catalyzed (Ru,11 Rh,12 Ir,13 Pd14) TH
reactions for the synthesis of quinolines from 2-aminobenzyl
alcohols with ketones or alcohols have been documented
(Scheme 1, eq 1). Despite the high efficiency and good
selectivity of these TH protocols, high temperature and
equivalent unsaturated substrates (carbonyls or alkylenes) as
SHAs are needed. Apart from the work above, Cai and the co-
workers13d demonstrated the efficient synthesis of quinolines
from allylic alcohols and oABAIs via iridium-catalyzed tandem
cyclization that also need excess allylic alcohols as SHAs (eq 2).
Considering the aforementioned drawbacks, the search for
step- and atom efficiency synthetic methods with mild
reaction conditions for the construction of quinolines is still
demanding.
Introduction
Quinoline derivatives represent a very important class of N-
heterocycles because of the wide range of their
pharmaceutical and biological activities such as anti-
inflammatory,1 antimalarial,2 neuroprotection,3 antipakinson,4
etc. In addition, quinolines can also serve as valuable building
blocks for manufacturing photoelectric materials5 and dyes.6
Owing to these significant functions, considerable effort has
been made to the development of effective methods to
construct functionalized quinolines. As is well known, some
classic name reactions such as the Skraup, Combes, Doebner–
von Miller, Conrad–Limpach, and Pfitzinger quinoline
syntheses are well-established.7 However, these conventional
synthetic routes are more or less limited in harsh reaction
conditions, low chemo-selectivity, multiple steps and low
product yields. By contrast, the Friedländer annulation8 is one
of the most simple and practical approaches for the
construction of quinolines, but the disadvantage is that the
substrates 2-aminobenzaldehydes are both unstable and
expensive. Hence, it is quite essential to find out cheap and
stable alternative reactants.
Previous work
O
R3
R3
R2
OH
[M]
R1
(1)
R1
or
OH
+
NH2
N
R3
1
Notably, Cho and Shim9 first reported the Ru-catalyzed
indirect Friedländer reaction that utilized easily available 2-
aminobenzyl alcohols (oABAIs) to react with ketones. The
R2
M = Ru, Rh, Ir or Pd
need carbonyls or alkylenes as SHAs
1
OH
O
R3
(2)
NaBH4
R3 step 1
[Ir], KOH
R1
R2
(2 equiv)
R3
Tol, 100 o
step 2
C
R2
mechanism shows the reaction undergoes
a transfer
N
R2
hydrogenation (TH) process. In recent years, TH strategy10 has
emerged as a super synthetic tool to promote the utilization of
alcohols, which allows effective elaboration of various
need allylic alcohols as SHAs
This work
R1
[IrCp*Cl2]2
t-BuOK
t-amyl alcohol
R3
O
OH
+
NH2
R1
(3)
R2
R3
N
R2
rt, N2
step- and atom efficiency
mild reaction conditions
operational simplicity
Scheme 1 Synthesis of quinolines from oABAIs by TH reactions.
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Considering the effective utilization of hydrogen from presence of [IrCp*Cl2]2 (entries 7-10). However, all these solvents
alcohols in TH strategy and the important significance of decreased the yield in different degrees relative to TAA. Next, we
quinoline synthesis, we became interested in exploring the tended attention to the effects of various bases (entries 11-14).
straightforward annulation of 2-aminobenzyl alcohols with Obviously, weak inorganic bases like K2CO3 and Cs2CO3 were difficult
enones. We envisioned that a catalytic system can transfer the to furnish the desired compound, and half equivalent of t-BuOK was
hydrogen from 2-aminobenzyl alcohols to α, β-unsaturated found to be better for the formation of 3aa (entry 15), indicating
carbonyl compounds to form 2-aminobenzaldehydes and that the base plays an important role in this TH annulation.
ketones directly, then followed by Friedländer annulation to Interestingly, the absence of metal catalyst also could afford a
o
generate quinolines (Scheme 1, eq 3).
certain amount of 3aa by heating to 100 C but along with a lot of
side reactions (entry 16), which might proceed a Meerwein–
Pondorf–Verley–Oppenauer (MPV-O) type hydrogen transfer
process.15 Finally, the evaluation of temperature showed that
heating could not promote the transformation (entry 17). Thus, the
optimal conditions are as described in entry 4 of Table 1.
Results and discussion
Table 1 Screening of optimal reaction conditions a
[IrCp*Cl2]2 (1 mol%)
O
OH
R3
t-BuOK (50 mol%)
Entry
1
Catalyst
Solvent
TAA
Base
Yieldb (%)
5
+
R2
R3
t-amyl alcohol (1.2 mL)
NH2
N
R2
3, isolated yield
rt, N2
Ru3(CO)12
t-BuOK
1a
2
Ph
2
RuCl2(PPh3)4
Co2(CO)8
TAA
TAA
t-BuOK
t-BuOK
t-BuOK
t-BuOK
t-BuOK
t-BuOK
t-BuOK
t-BuOK
t-BuOK
KOH
6
N
Ph
N
Ph
Cl
N
Ph
3
trace
3aa, 81%
3ab, 89%
3ac, 83%
OMe
4
[IrCp*Cl2]2
IrCl3·3H2O
Pd(OAc)2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
[IrCp*Cl2]2
-
TAA
86
5
TAA
45
N
Ph
I
N
Ph
Br
N
Ph
6
TAA
trace
3ad, 80%
3ae, 78%
3af, 62%
7
toluene
DMF
Diox
MeOH
TAA
59
8
8
N
Ph
CF3
N
Ph
N
Ph
N
3ag, 78%
3ah, 80%
3ai, 76%
OMe
O
9
41
47
N
S
10
11
12
13
14
15c
16
17e
78
N
Ph
N
Ph
N
Ph
3aj, 72%
3ak, 84%
3al, 77%
TAA
CH3ONa
K2CO3
71
Ph
TAA
ND
N
N
Ph
N
N
TAA
Cs2CO3
t-BuOK
t-BuOK
t-BuOK
ND
3am, 82%
3an, 43%
3ao, 27%
+
3ao', trace
TAA
(36, 85, 86)
(trace, 28d)
(86, 81, 72)
Scheme 2 Synthesis of quinolines from 2-aminobenzyl alcohol
TAA
and enones. Conditions: Unless otherwise stated, the reaction
was performed with 1a (0.35 mmol),
2 (0.35 mmol), [IrCp*Cl2]2
[IrCp*Cl2]2
TAA
(1 mol%), t-BuOK (50 mol%) in TAA (1.2 mL) at room
a Unless otherwise stated, the reaction was performed with 1a
(0.35 mmol), 2a (0.35 mmol), Cat (1 mol%), base (50 mol%) in
solvent (1.2 mL) at room temperature for 12 h under N2. GC
temperature for 12 h under N2.
b
With the optimized reaction conditions in hand, we then
investigated the substrate scope of this iridium-catalyzed
c
yield using hexadecane as an internal standard. Yields are
with respect to use of 25 mol%, 75 mol% and 100 mol% t-
tandem reaction. First, a wide range of enones (2a
examined with 2-aminobenzyl alcohol 1a to form 2,3-
substituted quinolines (Scheme 2, 3aa 3ao). As shown in
–2o) were
d
e
BuOK, respectively. 100 oC. Yields are with respect to the
temperature at 50 oC, 70 oC and 90 oC, respectively.
-
Scheme 2, all the reactions proceeded smoothly with a good
tolerance of various substituted groups. Electron donating
groups or electron withdrawing groups at the phenyl ring of
the enones readily delivered desired products in good isolated
To examine our tentative idea, we chose the reaction of 2-
aminobenzyl alcohol 1a with chalcone 2a as a model reaction to
formulate an efficient catalytic system. By performing the reaction
in t-amyl alcohol (TAA) at rt for 12 h under N2 protection, six
commercially available metal catalysts were tested with t-BuOK
respectively (Table 1, entries 1-6). To our delight, [IrCp*Cl2]2
exhibited good catalytic activity to give 3-benzyl-2-phenylquinoline
3aa in 86% (entry 4). Encouraged by this result, several solvents
such as toluene, DMF, dioxane and MeOH were investigated in the
yields (3aa-3ai). The 3-(2-methoxyphenyl)-1-phenylprop-2-en-
1-one 2f leads to a moderate transformation, which was
attributed to the steric influence of 2-methoxyl probably (3af).
Furthermore, three kinds of five-membered heterocycles such
as furan, thienyl, N-methylpyrrole were introduced to the
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quinoline skeleton in satisfactory yields (3aj-3al). Besides, 3-
benzyl-2-(p-tolyl)quinoline 3am was also obtained in good
yield. Specifically, 1-phenylprop-2-en-1-one resulted in a
deficient conversion to 3-methyl substituted quinoline 3an
,
possibly owing to the easily polymerizable property of the
terminal olefin motif. To investigate the effect of aliphatic
enone, 4-methylpent-3-en-2-one 2o reacted with 1a to give
the quinoline 3ao in a relatively low yield, and the regioisomer
3ao’ was trace in GC-MS detection.
Scheme 4 Synthesis of quinolines from 1a and cyclic enones.
To evaluate the applicability of cyclic enones, we used
cyclohex-2-en-1-one and benzoquinone to react with 1a under
standard conditions respectively (Scheme 4). However, these
two reactions could not deliver the desired products, as the
benzoquinone was quite easy to form hydroquinone and the
cyclohex-2-en-1-one was inclined to generate various fused
ring by-products.
Scheme 5 One pot reaction for the synthesis of 3aa
.
Considering the enones could be easily formed in ethanol
with base under mild conditions, we were quite interested in
making the integration of this aldol reaction and TH annulation
in one pot (Scheme 5). In order to maintain the efficient TH
process, we used t-BuOK and TAA to serve as the base and
solvent respectively in the synthesis of chalcone 2a (step 1).
Two hours later, [IrCp*Cl2]2 and 1a were introduced into the
reaction vessel without purification (step 2). The result showed
that this one pot two step reaction supplied quinoline 3aa in
an isolated yield of 62% which was lower than that obtained
via the reaction of purified 2a
.
To gain insight into the reaction mechanism, several control
experiments were performed under standard conditions. The
model reaction from 1a and 2a was interrupted to analyse the
intermediates after 2 hours. By means of GC-MS analysis,
quinoline product 3aa, 2-aminobenzaldehyde 1a’ and 1,3-
diphenylpropan-1-one 2a’ were detected in 43%, 1%, and 4%
yields, respectively (Scheme 6, eq 4), indicating rate-
determining step might be dehydrogenation of 2-aminobenzyl
alcohol 1a. However, the reaction of 1a’ with chalcone 2a
failed to provide product 3aa (eq 5). Besides, treatment of 2c
with equivalent 1a’ and 1b gave both products 3ac and 3bc in
similar yields (eq 6). From the above reactions, it is clear that
alcoholic hydroxyl group as hydrogen resource plays a crucial
role in this protocol that probably undergoes a pathway of
transfer hydrogenative coupling.
Scheme 3 Synthesis of quinolines from 2-aminobenzyl alcohols
and enonesa Unless otherwise stated, the reaction was
performed with
1 (0.35 mmol), 2 (0.35 mmol), [IrCp*Cl2]2 (1
mol%), t-BuOK (50 mol%) in TAA (1.2 mL) at rt for 12 h under
N2.
In addition to enones, we sought to probe the substrate
scope of 2-aminobenzyl alcohols, as described in Scheme 3.
Different substituted 2-aminobenzyl alcohols (1b-1f) could
effectively enable this new indirect Friedländer annulation.
Gratifyingly, halogen on the phenyl ring was well tolerated, as
exemplified by the presence of Cl or F atom (3bc-3ck).
Compared with (2-amino-5-chlorophenyl)methanol 1b, fluoro-
substrate 1c experienced a little decrease of transformation
which probably due to the fade of the nucleophilicity of amino
group. Apart from halogen, the methoxy group also had great
compatibility in this catalytic platform (3dk). Furthermore,
methyl substituted amino-alcohols (1e and 1f) were effective
transfer hydrogenative coupling partners to supply the
corresponding quinoline products (3ea-3fl).
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In conclusion, we have demonstrated a new method for the
synthesis of quinolines from easily available enones and 2-
aminobenzyl alcohols by utilizing a commercially available
catalyst system. The mechanism investigation indicates it
undergoes a hydrogen-transfer coupling strategy that enables
the synthetic protocol in an atom- and step-economic fashion
together with the merits of broad substrate scope, mild
conditions, operational simplicity, no need for external
reducing reagents and water as the only by-product, which
offers a practical alternative to access quinoline derivatives.
Conflicts of interest
There are no conflicts to declare.
Scheme 6 Control experiments.
Acknowledgements
Based on metal-catalyzed TH mechanism reported in the
literatures16 and the above control experiments, a plausible
reaction pathway is proposed in Scheme 7. First, IrCp*Cl2 and
t-BuOK proceed a ligand exchange process to generate
We gratefully acknowledge the financial support by Nantong
University, the Natural Science Foundation of China (Grant
Nos. 81302628), the Project of “Jiangsu Six Peaks of Talent”
(2014-SWYY-044 and 2016-SWYY-CXTD-008), the Project of
“Jiangsu 333 high-level talents”, and also thank the testing
service provided by Analysis and Testing Center in Nantong
University.
complex
to give alkoxide
aminobenzaldehyde 1’ and metal hydride
undergoes coordination with and then experience
hydrometallation to afford intermediate . Subsequently, with
the alcoholysis of by alcohol , transfer hydrogenation
product ketone 2’ is produced, and alkoxide is regenerated
A
which upon reaction with 2-aminobenzyl alcohol
which followed by β-H elimination to form 2-
. Next, enone
1
B
C
2
C
E
E
1
Notes and references
B
to accomplish the catalytic cycle. Finally, the formed 2-
aminobenzaldehyde 1’ and ketone 2’ undergoes the classic
Friedländer annulation with the assist of t-BuOK to provide the
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