The cooperative FeCl3/DDQ system for the regioselective synthesis of 3-arylindoles from β-monosubstituted 2-alkenylanilines

Article abstract of DOI:10.1039/c6ob00074f

A highly regioselective synthesis of 3-arylindoles by using the cooperative FeCl₃/DDQ system has been developed. This new protocol represents an attractive route for the synthesis of 3-arylindoles from readily accessible non-indole precursors, β-aryl-substituted 2-styrylanilines, using an inexpensive catalyst and oxidant. Noteworthy is the unique synergetic and synergistic effect of FeCl₃ and DDQ on the 1,2-aryl migratory process.

Full text of DOI:10.1039/c6ob00074f

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DOI: 10.1039/C6OB00074F
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Cooperative FeCl3/DDQ System for the Regioselective Synthesis of
3-Arylindoles from β-Monosubstituted 2-Alkenylanilines
Su San Jang and So Won Youn*
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A highly regioselective synthesis of 3-arylindoles by using the
cooperative FeCl3/DDQ system has been developed. This new
protocol represents an attractive route for the synthesis of 3-
arylindoles from readily accessible non-indole precursors, β-aryl-
substituted 2-styrylanilines, using inexpensive catalyst and oxidant.
Noteworthy is the unique synergetic and synergistic effect of FeCl3
and DDQ on the 1,2-aryl migratory process.
Scheme 1 2- or 3-Arylindole synthesis from 2-alkenylanilines
Indoles are one of the most significant heterocycles found in a
wide range of natural products, pharmaceuticals, and other
functional molecules.1 Among them, 3-arylindoles are known to
possess various biological properties2 and also have been
utilized for the synthesis of numerous natural products and
pharmacologically important compounds.3 Consequently, a
diverse range of synthetic methods for the formation of 3-
arylindoles from non-indole4 or indole5 precursors have been
developed.
mediated C-H amidation (Scheme 1, bottom).
In recent years, iron salts have attracted considerable attention
as effective catalysts due to their low cost, abundance, non-
toxicity, and environmentally benign properties.7 Several
examples have been reported on the oxidative coupling
reactions catalyzed by FeCl3 as a Lewis acid in the presence of
DDQ as an oxidant.7-8 However, to the best of our knowledge,
Fe-catalyzed oxidative C-N bond forming process involving 1,2-
aryl migration has not been developed.
Herein we disclose a highly regioselective synthesis of 3-
arylindoles from β-aryl monosubstituted 2-alkenylanilines in
the presence of FeCl3 and DDQ as a catalyst and oxidant,
respectively. In particular, the peculiar effect of FeCl3 in the
presence of DDQ on the 1,2-aryl migratory process is highly
noteworthy. This protocol could be complementary to other
Recently, our group reported an operationally simple and
robust C-H amidation of 2-alkenylanilines by the use of DDQ
(2,3-dichloro-5,6-dicyanobenzoquinone)
for
the
straightforward access to a diverse array of indoles in excellent
yields (Scheme 1, top).6a In addition, the related Ag(I)-
mediated6b and Pd(II)-catalyzed6c indole forming reactions from
2-alkenylanilines have been also developed, in both which an
uncommon 1,2-migratory process of β-monosubstituted 2-
alkenylanilines with solvent- and/or oxidant-dependence was
demonstrated to be operative. However, the low
regioselectivities limited their synthetic utility, giving the
mixture of inseparable 3- and 2-substituted indole products
(3-:2- = ≤ 4.5:1). During the course of these studies, we
systematically examined various combination of Lewis acids and
oxidants, and a very intriguing effect of Lewis acid, especially
FeCl3, on the 1,2-aryl migration was observed in the DDQ-
methods (e.g., intramolecular cyclization of α-substituted 2-
4g
vinylanilines6a-b or enamines,4c,
intermolecular coupling
between anilines and terminal alkynes4a, 4d-f or cinnamic acids4h)
for the synthesis of 3-arylindoles using non-indole precursors,
albeit with somewhat limited substrate scope.
We began our investigations on a variety of Lewis acids using 1a
and DDQ as the test substrate and oxidant, respectively (Table
1, for complete data, see ESI). Gratifyingly, it was found that
FeCl3 promoted 1,2-phenyl migration significantly to afford 2a
along with 3a in a good combined, isolated yield (71%, 2a:3a =
7:1) (entry 1). In contrast, other Fe(II) and Fe(III) salts gave
comparable good yields of indole products but very low or no
degree of migration (entries 2-4). With the exception of InCl3,
other Lewis acids examined afforded 3a as a major or single
Center for New Directions in Organic Synthesis, Department of Chemistry and
Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea.
E-mail: sowony73@hanyang.ac.kr
† Electronic Supplementary Information (ESI) available: [Full experimental details
and characterization data]. See DOI: 10.1039/x0xx00000x
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Table 1 Optimization studies: Selected data
Table 2 Substrate scope
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DOI: 10.1039/C6OB00074F
Entry R1
R2
H (1a)
Fe(III)a Time
Yieldb (2:3)c
75% (89:11)
32% (100:0)
57% (100:0)
74% (89:11)
97% (89:11)
59% (100:0)
84% (0:100)
92% (0:100)
48% (100:0)
79% (96:4)
80% (91:9)
91% (92:8)
100% (89:11)
67% (100:0)
96% (91:9)
98% (90:10)
67% (100:0)
Entry Lewis Acid
Oxidant
DDQ
DDQ
DDQ
DDQ
DDQ
DDQ
DDQ
BQ
Cu(OAc)2
tBuOOtBu
DDQ
DDQ
DDQ
Time (h)
6
5
7
Yield (%)a 2a:3ab
1
FeCl3
91 (71)
90
7:1
1:7
1
Ph
10
5
4 h
2d
3
4-MeOC6H4 H (1b)
30 min
30 min
6 h
10 min
10 min
24 h
2
FeBr3
3
4
Fe2(SO4)3·xH2O
FeCl2
100
100
100
81
0:1
1:7
2:1
1:2
4-MeC6H4
3-MeC6H4
2-MeC6H4
H (1c)
H (1d)
H (1e)
10
15
10
15
10
10
10
15
10
20
8
4
5
5
InCl3
24
24
24
24
24
24
4
4
24
24
6d
7e
8e
9
10
11
12
13
14
15
16
17
1-Naphthyl H (1f)
6
7
Sc(OTf)3
CuCl2
100
10
1:24
2:1
4-NO2C6H4
3-CF3C6H4
4-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
2-MeC6H4
H (1g)
H (1h)
4-Me (1i)
4-MeO (1j)
4-Me (1k)
4-Cl (1l)
4-NO2 (1m) 25
3-Me (1n)
3-Cl (1o)
3-NO2 (1p)
2-MeO (1q) 10
8
FeCl3
24 h
9
FeCl3
52
40
(72)
(75)
(30)
(7)
1:12
1:1.4
8:1
8:1
0:1
30 min
10 min
30 min
1 h
10
11c
12c
13c-d
14c-e
FeCl3
FeCl3
FeCl3·6H2O
-
FeCl3·6H2O
2 h
-
10:1
10
20
15
30 min
20 min
8 h
Yields were determined by 1H NMR using trichloroethylene as an internal
a
standard. Value in parentheses indicates an isolated yield. b Determined by 1H NMR.
c
d
At 80 °C. 1a was recovered in 43-46% yield. e N-Ts-2-Phenylindoline (4a) was
2 h
obtained in 40% yield.
a
b
c
Amount (mol%) of the used FeCl3·6H2O. Isolated yield. Ratios of inseparable
isomers were determined by 1H NMR. d Using FeCl3. e At 120 °C.
product (entries 5-7). Other oxidants and solvents were
examined (entries 8-10 and see ESI): DDQ and ClCH2CH2Cl were
identified as the most effective oxidant and solvent, forming 2a
with high efficiency. Further optimization of reaction conditions
(entries 11-12) showed that lower reaction temperature was
beneficial for higher ratio of 2a to 3a, while the use of
FeCl3·6H2O instead of FeCl3 led to both comparable chemical
yield and ratio.
withdrawing aryl substituents such as NO2 resulted in no
rearrangement (entries 7-8), alluding to the involvement of a
cationic rearrangement.6, 9-10
Next, we investigated the effects of substituents (R2) residing on
the aromatic moiety of N-Ts-anilines (entries 9-17). Both
electron-donating and –withdrawing substituents were well
tolerated regardless of their position, showing an electronic
dependence. Electron-donating substituents appeared to
facilitate 1,2-aryl migration considerably rather than their
electron-withdrawing counterparts, leading to generally faster
Control experiment employing only DDQ gave 3a as a sole
product with a low conversion as our previous report6a (entry
13), whereas the use of only FeCl3·6H2O resulted in a very small
amount of indole products (7%, 2a:3a = 10:1) along with the
completion of the reactions and higher selectivities for 2 over 3.
corresponding indoline product (4a) in 40% yield (entry 14).
These findings indicate that there is a remarkable synergetic
and synergistic effect of FeCl3 and DDQ which are both essential
and can obviously increase the reactivity and selectivity for this
1,2-migratory transformation. Compared to several examples
on more general 1,2-aryl migration in indole forming reactions
from β,β-disubstituted 2-alkenylanilines,9 the related process of
β-monosubstituted 2-alkenylaniline derivatives has been very
rarely observed in very few examples even with only low
selectivities (3-arylindole:2-arylindole = 1:9.1 ~ 4.5:1),10 making
this finding of great interest and significance. To the best of our
knowledge, this represents the very first example of highly
selective 1,2-aryl migration using the cooperative FeCl3/DDQ
system for the regioselective synthesis of 3-arylindoles from β-
aryl-substituted 2-styrylanilines.
It should be noted that most reactions completed after rather
short reaction time and were quite sensitive to the amount of
Fe(III) catalyst. In general, when the used amount of FeCl3
increased, the ratios of
2 to 3 increased while the combined
yields decreased (Figure S1 in ESI). Unfortunately, efforts to
expand the scope of this protocol into a selective migration in
the related reaction of β,β-diaryl-2-alkenylanilines as well as
application to benzofuran synthesis were unsuccessful.
To gain mechanistic insight into this reaction, a series of control
experiments were performed. When 2a alone or the mixture of
2a and 3a were subjected to the standard reaction conditions,
only 2a was recovered in 45-50% yields without any 3a (Scheme
2a). On the other hand, trace amount of 2a was observed in the
reaction of 3a under the same conditions. All these reactions
produced some unidentified complex mixture along with
significant decomposition of indole compounds, 2a and 3a both.
In the light of our observation (Table 1, entry 14) and previous
reports11 on FeCl3-catalyzed inter- or intramolecular
hydroamination between N-Ts-amines and olefins, the reaction
of a putative intermediate, indoline 4a, either (1) under our
standard reaction conditions, (2) employing only FeCl3·6H2O as
With the optimized reaction conditions in hand, we first
explored the substituent effect (R1) at the alkene moiety. Both
electron-rich and -neutral aryl groups irrespective of the
position of their substituents could migrate to give the
corresponding 3-arylindole
2 with high selectivities and little
steric dependence (Table 2, entries 1-6). In contrast, electron-
2 | J. Name., 2012, 00, 1-3
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additive had deleterious effect, shutting down VtiehweArrtieclaecOtniloinne
either completely or to a large extentDO(SI:c1h0e.1m03e9/2Cc6)O.BI0n00t7h4eF
presence of BHT, the corresponding trapping product was
obtained as a byproduct. These results may suggest a
mechanism involving a radical intermediate during the reaction.
However, it cannot be ruled out that DDQ was consumed by its
direct reaction with these additives, thus leading to depletion of
DDQ oxidant and ineffective reaction as well as the formation
of a byproduct.
Scheme 2
a sole catalyst, or (3) using only DDQ was performed (Scheme
2b). No reaction occurred in the presence of only FeCl3·6H2O,
while DDQ promoted the oxidation reaction of 4a to afford only
3a. In sharp contrast, very intriguingly, the mixture of 2a and 3a
was obtained in the reaction of 4a under the standard reaction
conditions, albeit in a low yield and selectivity. After longer
reaction time, almost two times increase of the selectivity was
observed without increasing the chemical yield. On the other
hand, the reaction of the other regioisomeric indoline 5a under
the standard reaction conditions led to the formation of only 2a
quantitatively in only 1 h, so did that using only DDQ.
To further investigate if the generation of indoline
Scheme 3 Proposed mechanism
intermediates (i.e.,
4 or 5) and the transformation of 3 into 2
were involved during the reaction, the reaction of 1a (and 1p
was monitored by TLC and H NMR analyses by withdrawing
aliquots at regular intervals (Figure S2 in ESI). However, neither
)
Although a clear mechanistic picture is elusive at this juncture,
a plausible mechanistic proposal is presented in Scheme 3. FeCl3
might play two important roles as a Lewis acid8: (1) increasing
the oxidizing power by coordination with the carbonyl O atom
1
4a nor 5a (and the corresponding indolines derived from 1p
was observed. In contrast, products and were forming
continuously, while the ratio of to remained almost constant
)
2
3
of DDQ and (2) increasing the reactivity of substrate
1 by
2
3
chelation to promote an intramolecular cyclization for an initial
C-N bond formation. Two plausible mechanisms, i.e., either 1)
ionic8e, 8g or 2) radical8b mechanism can be conceived for this
oxidative cyclization reaction. In an ionic mechanism (Scheme
during the reaction. Interestingly, in comparison with the
outcomes in Scheme 2a, conspicuous decomposition of 2a and
3a was not observed during the reaction progress. These
findings suggest that initially generated both 2- substituted
indoles (e.g., 3a) and indolines (e.g., 4a) are the unlikely
intermediates in the rearrangement.
3a),8e, 8g species
, which is initially formed by a chelation of Fe(III) with
sulfonamide and alkene moieties of . Then sequential
B is generated by deprotonation from species
A
1
Inclusion of TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl), BHT
(3,5-di-tert-butyl-4-hydroxytoluene), or ascorbic acid as an
intramolecular C-N bond and intermolecular C-O bond forming
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J. P. Tillement, J. Pharmacol. Exp. Ther., 1989, 249, 288; (c) K.
reactions between
to Fe(III) takes place to afford the species
intermediate is most likely to undergo a 1,2-aryl migration
directly (path a) or indirectly via (path c) to give and
regenerate the catalytically active Fe(III) species along with
HDDQ‾. Subsequent deprotonation of by HDDQ‾ forms the
desired 3-arylindole . The formation of 2-arylindole can be
derived from re-aromatization directly from (path b) or
through (path c) by the loss of a proton. When an aryl
substituent (Ar) is not electron-rich enough, its expected much
less or no participation in the process of can explain the
only formation of (e.g., 3g and 3h, Table 2, entries 7-8).
Alternatively, a radical mechanism could be also conceived
(Scheme 3b).8b Species
is oxidized by DDQ to afford the
electrophilic Fe(IV) species , which then undergoes an alkene
insertion to generate . Next, the intermediate is most likely
to undergo a 1,2-aryl migration directly (path a) or indirectly via
(path c) to give along with Fe(II), which is reoxidized by
HDDQ• to regenerate the catalytically active Fe(III) species. As
mentioned above, subsequent deprotonation of by HDDQ‾
occurs to give . In this pathway, FeCl3 seems to be involved in
single electron transfer process as an essential catalyst for the
reaction. However, 1,2-aryl migration in this oxidative
cyclization reaction was also promoted to some extent (albeit
less than FeCl3) by other Lewis acids (e.g., InCl3, Sc(OTf)3,
Yb(OTf)3, ZnCl2, MgCl2), which are incapable of catalyzing
oxidative coupling processes via higher oxidation state.
Therefore, although a mechanism remains elusive at this
juncture, the ionic mechanism seems to work more generally in
this cooperative Lewis acid (FeCl3)/DDQ system.
B
and the activated DDQ
C
by coordination
View Article Online
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In summary, we have developed a highly regioselective
synthesis of 3-arylindoles by using the cooperative FeCl3/DDQ
system, involving 1,2-aryl migration. This new protocol
represents an attractive route for the synthesis of 3-arylindoles
from non-indole precursors, readily accessible β-aryl-
substituted 2-styrylanilines, using inexpensive catalyst and
oxidant, mostly after short reaction time. Noteworthy is the
unprecedented, unique catalytic effect of FeCl3 in the presence
of DDQ on the 1,2-aryl migratory process.
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ref 6.
This work was supported by both the Basic Science Research
Program and Nano·Material Technology Department Program
through the National Research Foundation of Korea (NRF)
funded by the Ministry of Education and Ministry of Science, ICT
9
and
future
Planning
(nos.
2012R1A1A2041471,
2012M3A7B4049644, 2015R1A2A2A01002559, and 2014-
011165). We thanks Mr. Sung Hong Kim (Daegu Center, Korea
Basic Science Institute) for HRMS analysis.
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