Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives

Article abstract of DOI:10.1039/c7cc06448a

A method for the oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary stereocenters in good to excellent yields via sequential intramolecular oxidative arylacetoxylation, hydrolysis and oxidation steps.

Full text of DOI:10.1039/c7cc06448a

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DOI: 10.1039/C7CC06448A
Authors
S. Karnakanti,+ Z.-L. Zang,+ S. Zhao, P.-L. Shao, P. Hu* and Y. He*
Affiliations
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, School of
Pharmaceutical Sciences, Chongqing University, 55 Daxuecheng South Road, Shapingba,
Chongqing 401331, P.R. China.
Acknowledgements
We are grateful for financial support from the National Natural Science Foundation of China (No.
21372267, 21402150, 21572027, 21602023) and the Postdoctoral Research Grant (2016M602658)
and Fundamental Research Funds for the Central Universities (10611201CDJXY460001) for financial
support.

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Palladium-Catalyzed Oxidative Arylacetoxylation of Alkenes:
Synthesis of Indole and Indoline Derivatives
Received 00th January 20xx,
Accepted 00th January 20xx
DOI: 10.1039/x0xx00000x
www.rsc.org/
A method for oxidative arylacetoxylation of alkenes has been diverse range of biological activities.6 As a result, effective
developed to synthesize indole and indoline derivatives from methods for synthesizing indoles to access these classes of
readily accessible substrates. The cinnamyl tethered anilines with compounds have been actively investigated,7 and one of the
picolinamide as a directing group provided 3-substituted indoles most desirable strategy is via direct oxidative C-H
via intramolecular oxidative arylacetoxylation, and the 2-methyl functionalization. In particular, the construction of substituted
substituted cinnamyl anilines furnished indoline derivatives with indole
derivatives
via
intramolecular
oxidative
3-position quaternary stereocenters in good to excellent yields via functionalization is even more valuable.8 Similarly, indolines
sequential intramolecular oxidative arylacetoxylation, hydrolysis with a quaternary center at the 3-position are of considerable
and oxidation steps.
interest because of their remarkable prevalence in numerous
natural products and biologically active compounds.9 To
continue our research in palladium-catalyzed C−H
functionalization,10 herein we report the development of a
carbo-acetoxy functionalization method to efficiently
synthesize indole and indoline derivatives employing a similar
palladium catalytic system.
Metal catalyzed oxidative difunctionalization of alkenes is
an emerging field which establishes multiple bonds in a single
operation to facilitate the synthesis of organic molecules from
simple starting materials without the requirement of
prefunctionalizations.
Intramolecular
carbo-
heterofunctionalization of unsaturated bonds of alkenes or
alkynes proved to be an efficient synthetic strategy to access
various heterocyclic natural products.1 In recent years,
transition-metal-catalyzed oxidative C(sp2)-H functionalization
directed by a functional group has been recognized as an
increasingly viable method to construct C-X (X = carbon or
heteroatom) bonds.2 In these reactions, directing groups are
essential for acceleration and regioselective controls,3 and the
intermolecular version has been under active investigation and
proven to be highly fruitful.4 In contrast, the intramolecular
oxidative arene/olefin coupling, especially with unactivated
olefins, has been poorly studied.5 We envisioned that such an
intramolecular reaction of electronrich arenes with
unactivated olefins could provide an efficient synthesis of
indole and indoline derivatives.
We began the investigation of the intramolecular
carboacetoxy functionalization using anilide 1a as a model
substrate, which contains a tethered cinnamyl moiety and a
picolinamide (PA) as an easily removable directing group
(Table 1). After screening various reaction conditions, we
isolated the desired spiro-dihydroqunoline 2a in 68% yield
employing the following catalytic system [Pd(OAc)2 (0.10
equiv), PhI(OAc)2 (2.50 equiv), 2-chloro-4-cyanopyridine
(PyClCN, 0.40 equiv), 110 °C,
2 h, toluene], and the
concentration of 1a in toluene was 0.075 mol/L (entry 1). We
then investigated the role of each reactant by performing
various control experiments. As expected, Pd(OAc)2 and
PhI(OAc)2 played pivotal roles in the transformation, and no
reaction was observed in the absence of them (entry 2).
Various Pd(II) catalysts such as PdCl2(PhCN)2, PdCl2(PPh3)2, or
PdCl2(dppf) were examined and found to be less effective than
Pd(OAc)2, providing the desired product in significantly lower
yields (15−42%) (entries 3-5). Other common metal catalysts
such as FeCl3, RuCl3, Sc(OTf)3, Bi(OTf)3, or In(OTf)3 could not
initiate this reaction (entry 6). Omitting PyClCN led to low
yield, confirming its essential role in the reaction (entry 7). Use
of various additives such as PhCN, 2,2- bipyridine, S-BINAP, or
S-BINAL resulted in lower yields (entries 8-11), and varying the
solvent or lowering the reaction temperature did not improve
Many heterocycles including natural products possessing
an indole core are important structural motifs as they display a
† Electronic Supplementary Information (ESI) available: CCDC 1562681, 1562684.
For ESI and crystallographic data in CIF or other electronic format see DOI:
10.1039/x0xx00000x
+ These authors contributed equally to the manuscript.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 1
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Table 1 Optimization of the arylacetoxylation reactiona
Journal Name
Scheme 1 Synthesis of indole derivativesa
entry
variation from the "standard" condition
yield (%)
1
2
3
4
5
none
68
0
without Pd(OAc)2 or PhI(OAc)2
PdCl2(PhCN)2 instead of Pd(OAc)2
PdCl2(PPh3)2 instead of Pd(OAc)2
PdCl2(dppf) instead of Pd(OAc)2
42
21
15
FeCl3, RuCl3, Sc(OTf)3, Bi(OTf)3 or In(OTf)3
instead of Pd(OAc)2
6
0
7
without PyClCN
48
55
< 5
< 5
< 5
41
25
28
45
0
8
PhCN instead of PyClCN
2,2-bipyridine instead of PyClCN
S-BINAP instead of PyClCN
S-BINAL instead of PyClCN
DCE instead of toluene
dioxane instead of toluene
CH3CN instead of toluene
80 °C instead of 110 °C
PA replaced by Me
9
10
11
12
13
14
15
16
17
18
aReaction conditions:
1 (0.3 mmol), Pd(OAc)2 (0.03 mmol), PhI(OAc)2
(0.75 mmol), PyClCN (0.12 mmol), toluene (4 mL), N2, 2 h. bYield was
that of the isolated product. cYield in parentheses on gram scale.
dPd(OAc)2 (0.03 mmol), PhI(OAc)2 (0.75 mmol), Ac2O (1.5 mmol), AcOH
(1.5 mmol), 2 h.
withdrawing aryl groups at the tethered chain were well-
tolerated and afforded the corresponding substituted indoles
(
2o-u) in good yields. However, attempts to utilize a terminal
alkene devoid of an aryl moiety for the cascade reaction were
unsuccessful (see ESI).
PA replaced by Ac
0
PA replaced by Ts
0
After establishing an efficient route to a variety of indole
derivatives, we were interested in extending the method to
prepare indoline derivatives by exploring the reaction with
substrates bearing a methyl substitution at double bond of
cinnamyl tethered anilides (Scheme 2). It was found that
anilides containing typical electron donating and electron
withdrawing functional groups, such as p-Me, p-Et, p-iPr, p-tBu,
p-OMe, p-F, p-Cl and p-CF3, were well tolerated. All the
indoline-forming reactions delivered diasteremeric mixtures
(≤2:1), and so all the studied examples were subjected to
hydrolysis and followed by oxidation to afford the
corresponding indoline derivatives 4a-i in good yields.
aAll reactions were carried out on a 0.3 mmol scale. bYield was that of
the isolated product
the yield (entries 12-15). The reaction did not occur if the PA
group was replaced by Me, Ac or Ts group (entries 16-18),
suggesting the critical role of PA.
With the optimized conditions established, the generality
of the carbo-acetoxy functionalization reaction was
subsequently investigated (Scheme 1), and the electronic
effects of different aniline substituents (R) were examined.
Introduction of an electron-donating group, such as p-Me, p-
Et, p-iPr, p-tBu and p-OMe, to the anilide moiety of
1 led to the
corresponding products 2b-f in good yields (66−81%).
Substitutions of electron-withdrawing p-F, p-Cl, p-COMe, p-
CO2Me and p-CF3 groups on N-aryl ring were well tolerated,
and provided 2g-k in slightly reduced yields (51-68%),
presumably due to the lower nucleophilicity of the N-aryl
moiety. However, substrate bearing cyano group (1l) at the
para-position, turned out to be a difficult one, did not afford
The products of this reaction could be easily converted into
useful entities (Scheme 3). The hydrolysis is non-selective and
both acetyl and picolinamide groups could be readily removed
in one pot by using aqueous 10% NaOH at 0 °C to afford (1H-
indol-3-yl)(phenyl)methanol, which upon selective N-
protection with (Boc)2O and oxidation of hydroxyl group with
Dess–Martin periodinane afforded the 3-acylindole derivative
5a. The related 3-acylindoles represent an important class of
biologically active heterocyclic compounds such as
pravadoline, ramosetron and BPR0L075,11 and our method
provides a rapid access to the core structure of these
compounds. Interestingly, when we perform the hydrolysis
the desired product. Substrate with m-OMe substitution (1m
)
was chosen to test the regioselectivity of the reaction, which
selectively cyclized to produce the 6-methoxy indole (2m) as
the predominate product (2m : 2m' = 5:1) as confirmed by 1H-
NMR analysis. Substrates bearing o-Me also afforded the
corresponding products 2n in 66% yield. Interestingly,
2 | J. Name., 2012, 00, 1-3
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Scheme 2 Synthesis of indoline derivativesa
respectively. The scope of this synthesis and the application of
alkylideneindolenine intermediates for the synthesis of indole
alkaloids are under study.
To gain some mechanistic insight, the picolinyl protected 3-
benzylindole (9a) was synthesized to examine the possibility of
acetoxylation at the benzylic position. As shown in Scheme 4,
under the optimized conditions, the reaction did not afford the
desired product 2a (see ESI). This result suggest that the
mechanism for arylacetoxylation of 1a is not via the stable 3-
benzylindole intermediate.
Scheme 4 Attempted acetoxylation on 3-benzylindole 9a
On the basis of our observations and previous mechanistic
studies,13
a plausible mechanism for the formation of
indoles/indolines is depicted in Scheme 5. The
difunctionalization may proceed via arene palladation with
subsequent olefin insertion followed by oxidation to high-
valent palladium (IV) intermediate with diacetoxyiodobenzene
as the oxidant, which undergoes sequential acetoxylation and
reductive elemination to afford the compound 2a. In case of
substrate 3a, due to methyl group substitution, isomerization
aReaction conditions: (1)
PhI(OAc)2 (0.75 mmol), PyClCN (0.12 mmol), toluene (5 mL), N2, 110 °C,
3 h. (2) K2CO3, MeOH/H2O, r.t, 3 h. (3) DMP, DCM, r.t, 2 h. bYield was
that of the isolated product. See Supporting Information for details.
3 (0.3 mmol), Pd(OAc)2 (0.03 mmol),
restricted and acetoxylation afforded the compound 4a
.
using NaOH in MeOH/H2O as solvent produced methoxy
substituted indole derivative 6a via alkylideneindolenine
intermediate
(
Int-I).12 Moreover, compound 2a was
Scheme 5 Plausible reaction mechanism
transformed into various heteroatom substituted indole
derivatives 7a and 8a using propane-2-thiol and benzylamine,
Scheme 3 Derivatization of 2aa
O
N
O
O
5a
1. NaOH, THF:H2O, 0 °C
2. (Boc)2O, DMAP
3. DMP, DCM
AcO
O
In summary, we have developed a method to access indole
and indoline derivatives from simple substrates in
NaOH
benzylamine
DMF:H2O, r.t
81%
HN
NaOH
a
N
MeOH:H2O, r.t
88%
N
N
H
straightforward and efficient manner. Bearing picolinamide as
a directing group, the cinnamyl anilines (1a-u) cyclized to
afford indoles (2a-u) in moderate to good yields via direct
oxidative arylacetoxylation, while the 2-methyl substituted
O
N
H
8a
2a
6a
NaOH
propane-2-thiol
DMF:H2O, r.t
75%
N
Int-I
cinnamyl anilines (3a-i) furnished the indoline derivatives (4a-i
)
in good yields via sequential oxidative arylacetoxylation,
hydrolysis and oxidation steps. Studies to establish an
asymmetric oxidative arylation are currently ongoing in our
laboratory.
S
N
7a
H
aSee Supporting Information for details.
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Journal Name
7
8
Synthesis of indoles through palladium-catalyzed reactions
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Conflicts of interest
There are no conflicts to declare.
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DOI: 10.1039/C7CC06448A
A method for oxidative arylacetoxylation of alkenes has been developed to synthesize
indole and indoline derivatives from readily accessible substrates.