Microwave-Assisted Domino Palladium Catalysis in Water: A Diverse Synthesis of 3,3′-Disubstituted Heterocyclic Compounds

Article abstract of DOI:10.1002/ejoc.201800155

An environmentally benign microwave-assisted domino [Pd]-catalyzed reaction, for the efficient and diverse synthesis of 3,3′-disubstituted indolines, oxindoles, and dihydrobenzofurans, is presented. Significantly, water served as the sole green solvent and the strategy displayed an excellent functional-group tolerance. Remarkably, the process was also amenable to unmasked functional groups and furnished the products, in very good to almost quantitative yields.

Full text of DOI:10.1002/ejoc.201800155

A Journal of
Accepted Article
Title: Microwave Assisted Domino [Pd]-Catalysis in Water: A
Diversified Synthesis of 3,3'-Disubstituted Heterocyclic
Compounds
Authors: Ramesh Karu, Suchand Basuli, and Gedu Satyanarayana
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To be cited as: Eur. J. Org. Chem. 10.1002/ejoc.201800155
Link to VoR: http://dx.doi.org/10.1002/ejoc.201800155
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10.1002/ejoc.201800155
European Journal of Organic Chemistry
COMMUNICATION
Microwave Assisted Domino [Pd]-Catalysis in Water: A
Diversified Synthesis of 3,3’-Disubstituted Heterocyclic
Compounds
Karu Ramesh, [a] Suchand Basuli [a] and Gedu Satyanarayana*[a]
compounds (indolines[5], oxindoles[6] and dihydrobenzofurans[7])
Abstract: An environmentally benign microwave assisted domino
[Pd]-catalysis, for the efficient and diversified synthesis of 3,3’-
disubstituted indolines, oxindoles and dihydrobenzofurans, was
presented. Significantly, water served as the sole green solvent and
the strategy displayed an excellent functional group tolerance.
Remarkably, the process was also amenable to unmasked functional
groups and furnished the products, in very good to near quantitative
yields.
constitutes chief structural cores of natural products and
pharmaceutical compounds [Figure 1 (A, B, C, E)[8a] (D),[8b] (F,
G)[8c, 8d]]. Among the many classical approaches,[9] particularly,
[Pd]-catalyzed domino intramolecular Heck and subsequent C−H
functionalization,[10] has proved to be of high significance. The
most significant initial results of this sort, were well established by
Ronald Grigg and co-workers.[11],[12] Stivala et al and Vachhani et
al, respectively, developed Heck and boration strategy, under
microwave irradiation. Stivala and co-workers, described
synthesis of aza-indolines via Heck and Suzuki coupling.
Whereas indolinone-3-methyl boronic esters, were accomplished
by the research group Vachhani.[13],[14] Notably, 3,3’-disubstituted
indolin-2-ones containing alkynyl moiety, were synthesized by the
research groups of Li and Guo, which, in fact, broadens the scope
of this concept.[15] To the best of our knowledge, there is no
general strategy for the preparation of different 3,3′-disubstituted
heterocycles bearing alkynyl functionality, particularly, for the
synthesis of indolines. In this context, very recently, we reported
an efficient strategy for the synthesis of alkyne substituted
dihydrobenzofurans via a domino intramolecular Heck and
Sonogashira coupling, under microwave assisting conditions. [16]
Introduction
In the recent past, development of environmentally benign
synthetic strategies are in great demand to sustain the ecology of
our globe.[1] Green chemistry emerged as an essential alternative
to the otherwise very harsh conventional reaction conditions.[2]
The use of toxic and volatile organic solvents contributes to the
detrimental impact on the environment and may also cause an
insufficient E-factor.[3] Therefore, development of chemical
processes using green solvents has been one of the main facet
of green chemistry.[4] In this context, water is unique, ubiquitous,
and renewable polar solvent. Due to its inherently safe, non-
flammable nature, it has been regarded as green solvent.
In addition, the use of unconventional strategies, such as,
microwave irradiation technique has become evident as an
excellent alternative to conventional synthetic processes. The
microwave driven chemical strategies are beneficial, as: i) energy
efficient; ii) the reaction completes in short span of time; iii) and
high products yields and purity. Furthermore, domino processes
contribute to the green synthesis by enabling the formation of
multiple bonds, in a single pot via minimizing the detrimental
impact of step-wise synthesis. Accounting the advantages of
multiple bonds formation in an environmentally benign approach,
we aimed at the one-pot domino strategy with microwave
assistance, under environmentally benign conditions.
Fig. 1 Natural products and drugs having Indoline, oxindole,dihydrobenzofuran
core structure.
In continuation of our ongoing research interests on the
development of domino one-pot processes, [17] herein, we present
efficient and environmentally benign microwave assisted domino
[Pd]-catalysis, for a diversified synthesis of 3,3’-disubstituted
indolines, oxindoles and dihydrobenzofurans. Notably, unlike
earlier reports, this method is first of its kind on deliberating the
synthesis of indolines. Significantly, this strategy is successful
using water as the sole green solvent. This greener method
involves a domino intramolecular Heck[18] and intermolecular
Sonogashira couplings.[19] Remarkably, this process showed
Recently, investigations on establishing green chemical
processes, for the synthesis of functionalized heterocyclic
compounds of biological relevance has become crucial part of
organic synthesis. In particular, 3,3’-Disubstituted heterocyclic
[a]
Indian Institute of Technology (IIT) Hyderabad, Kandi – 502 285,
Sangareddy District, Telangana, INDIA
Fax: +91(40) 2301 6032
E-mail: gvsatya@iith.ac.in
Home page:
https://sites.google.com/site/gsresearchgrouphomepage/home
excellent functional group tolerance and even successful without
protecting the reactive functionalities (e.g. amine, hydroxyl and
carboxylic acid groups).
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10.1002/ejoc.201800155
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improvement even by increasing the microwave irradiation time
and with other bases (Table 1, entries 2 to 5). Also, Pd(OAc)2 in
conjunction with phosphine ligands, showed no improvement
(Table 1, entries 6 & 7). While the reaction in the presence of
Result and Discussions
To begin with, it was intended to explore the reaction with the
assistance of microwave irradiation, under different conditions, in
order to identify the best optimal conditions. Particularly, it was
aimed to conduct the reaction in water as the sole reaction
medium. Thus, ortho-iodophenyl allyl tertiary amine 1a and
phenylacetylene 2a, were chosen for this study. Initially, the
reaction was carried out under microwave irradiation, in the
presence of Pd2(dba)3 (1 mol%), base K2CO3 (3 equiv) in H2O (0.5
mL), at 100 C for 20 min. The desired indoline product 5aa was
obtained, in very poor yield (Table 1, entry 1). There was no
Pd(OAc)2/BINAP
and
quaternary
ammonium
salt
[benzyltriethylammonium chloride (BTEAC)], as an additive,
furnished 5aa, in moderate yield (Table 1, entry 8). Interestingly,
Pd2(dba)3/K2CO3 and additive BTEAC, was found to be suitable
and gave the product 5aa, in 75% yield (Table 1, entry 9). While
the reaction with tetrabutylammonium bromide (TBAB) and
tetrabutylammonium iodide (TBAI), as additives, gave the product
5aa, in 62% and 55% yields, respectively (Table 1, entries 10 &
11).
Table 1. Optimization for the formation of indolines 5aa from 2-iodo-N-alkyl-N-(2-methylallyl)anilines 1a and phenyl acetylene 2a.a,b,c
entry
catalyst
(1 mol%)
ligand
(10
additive
(1 equiv) (3 equiv)
base
Solvent tem time yield
p
(min 5aab
mol%)
)
(%)
(C)
1
2
3
4
5
6
7
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd(OAc)2
Pd(OAc)2
-
-
-
-
-
-
-
-
-
-
-
K2CO3
K2CO3
Na2CO3
NaOH
Cs2CO3
K2CO3
K2CO3
H2O
H2O
H2O
H2O
H2O
H2O
H2O
100 20
100 40
100 40
100 40
100 40
100 15
100 15
(10%)
(15%)
trace
(12%)
trace
(10%)
-
PPh3
Xantph
c
-
os
8
9
Pd(OAc)2
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd2(dba)3
Pd(PPh3)4
PdCl2
BINAP
BTEAC K2CO3
BTEAC K2CO3
H2O
H2O
H2O
H2O
H2O
H2O
100 20
100 20
100 20
100 20
100 20
100 15
100 15
100 15
100 15
100 10
(40%)
(75%)
(62%)
(55%)
trace
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
TBAB
TBAI
K2CO3
K2CO3
TBACH K2CO3
BTEAC NEt3
BTEAC Imidazole H2O
BTEAC Pyridine
BTEAC DBU
BTEAC DBU
BTEAC DBU
(40%)
c
-
c
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
H2O
ETOH
-
(98%)
(50%)
(62%)
(68%)
(64%)
(70%)
80
20
TBAB
TBAI
DBU
DBU
100 15
100 15
100 15
100 10
100 10
100 10
100 10
BTEAC DBU
BTEAC DBU
BTEAC DBU
BTEAC DBU
BTEAC DBU
c
-
c
Pd(PPh)3Cl2
Pd(TFA)2
Pd2(dba)3
-
c
-
(62%)
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26
Pd2(dba)3
-
BTEAC DBU
1,4-
Dioxane
EDC
100 10
100 10
(50%)
27
28
Pd2(dba)3
Pd2(dba)3
-
-
BTEAC DBU
BTEAC DBU
(15%)
(10%)
Toluene 100 10
aUnless otherwise mentioned, all the reactions were carried out under microwave irradiation in aqueous medium by using 71.7 mg (0.25 mmol) of 2-iodo-N-methyl-
N-(2-methylallyl)aniline 1a, 39.5 mg (0.37 mmol) of phenylacetylene 2a, base (0.75 mmol, 3 equiv), [Pd]-catalyst (1 mol%), ligand (10 mol%), and solvent-Water
(0.5 mL). bYields in the parentheses are isolated yields of product 5aa. cNo significant spot was observed on TLC; neither the starting material was recovered nor
any product was isolated.
Almost no progress was observed with tetrabutylammonium
chloride hydrate (TBACH) (Table 1, entry 12). On the other hand,
the reaction was inferior with nitrogen bases such as,
trimethylamine, imidazole and pyridine (Table 1, entries 13 to 15).
Gratifyingly, when 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was
employed as the base, in the presence of 1 mol% of Pd2(dba)3
and additive BTEAC, under microwave irradiation at 100 C for 15
min, the desired indoline product 5aa was obtained, in 98% yield
(Table 1, entry 16). The reaction for shorter reaction time (10 min)
at 100 C, gave the product in 50% yield (Table 1, entry 17).
However, at slightly low temperature (80 C), delivered the 5aa,
in 62% yield (Table 1, entry 18). While TBAB and TBAI as
additives along with the base DBU, afforded 5aa, in fair yields
(Table 1, entries 19 & 20). On the other hand, the reaction with
Pd(PPh3)4, base DBU and additive BTEAC, gave 5aa, in 70%
yield (Table 1, entry 21). While with other [Pd]-catalysts, the
reaction was inconclusive (Table 1, entries 22 to 24). On the other
hand, the reaction with organic solvents, gave the product 5aa, in
poor to good yields (Table 1, entries 25 to 28).
microwave irradiation, 100 C, 15 min (Table 1, entry 16)], to
demonstrate the scope of this green method, next, the reaction
was tested with different ortho-iodophenyl allylic amines 1a-1c
and acetylenes 2a-2o. To our delight, the method was found to
be quite amenable and afforded the corresponding alkyne
substituted indolines 5aa-3co, in very good to near quantitative
yields (Table 2). Notably, the reaction was suitable to aryl as well
as alkyl acetylenes. Significantly, the reaction was tolerable to
protecting group free amine functionality (5ae, 5be & 5ce, Table
2). Gratifyingly, the process was smooth enough with electron
withdrawing carboxylic acid group on the aromatic ring of aryl
acetylene 2f (5af, Table 2). In addition, the strategy was smoothly
amenable to cyclopropyl acetylenes (5ah & 5ch, Table 2).
Gratifyingly, the strategy was tolerable with aliphatic acetylenes
with protecting group free reactive hydroxyl group (5an, 5ao, 5bn,
5bo & 5co, Table 2). Significantly, the reaction was amenable
with testosterone acetylene 2p and furnished 5bp, as a
diastereomeric mixture. It is worth noting that the reaction is some
sort of more selective with ortho-iodophenyl allylic amines.
Because the reaction with the corresponding ortho-bromophenyl
allylic amines was sluggish.
With these optimal reaction conditions in hand [i.e.
Pd2(dba)3 (1 mol%), DBU (3 equiv), additive BTEAC (1 equiv),
Table 2: Synthesis of indolines 5aa-5fa from 2-iodo-N-alkyl-N-(2-methylallyl)anilines 1a-1f and terminal alkynes 2a-2p.a,b,c
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aReaction conditions: 2-iodo-N-alkyl-N-(2-methylallyl)aniline 1a-1f (0.25 mmol), acetylenes 2a-2p (0.37 mmol) Pd2(dba)3 (1 mol%), DBU (1,8-
Diazabicyclo[5.4.0]undec-7-ene)(3 equiv), and solvent Water (0.5 mL), 100 C, 15 minutes. bYields in the parenthesis are chromatographically isolated pure products.
cThe first alphabet of products 5aa-5fa refers to the 2-iodo-N-alkyl-N-(2-methylallyl)aniline, while the second letter indicates the acetylenes.
It is worth noting that the reaction of N-arylallylamine 1d with an
terminal alkyne 2a gave the product 5da with 86% of yield. But,
the process, the reaction was examined with ortho-iodophenyl
enamides 3a-3b and terminal acetylenes 2a-2p, under standard
microwave irradiation conditions. To our delight, the reaction was
quite successful and gave the desired oxindoles 6aa-6ap, in very
good to near quantitative yields (Table 3). Remarkably, the
reaction was compatible with different aryl or alkyl acetylenes.
Significantly, the reaction was tolerable with protecting group free
functional moieties such as amine, hydroxyl and carboxylic acid
groups.
unfortunately,
the
reaction
with
3-iodo-N,N-bis(2-
methylallyl)pyridin-4-amine 5e and 2-iodo-N-(2-methylallyl)aniline
5f were not successful (neither the starting material nor the
product was isolated).
After successful accomplishment of alkyne substituted
indolines 5aa-5fa (Table 2), further to ascertain the applicability of
Table 3: Synthesis of oxindoles 6aa-6ap from N-(2-iodophenyl)-N-alkylmethacrylamide 3a-3b and terminal alkynes 2a-2p.a,b,c
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aReaction conditions: N-(2-iodophenyl)-N-alkylmethacrylamide 3a-3b (0.25 mmol), acetylenes 2a-2p (0.37 mmol) Pd2(dba)3 (1 mol%), DBU (1,8-
Diazabicyclo[5.4.0]undec-7-ene)(3 equiv), and solvent Water (0.5 mL), 100 C, 15 minutes. bYields in the parenthesis are chromatographically isolated pure products.
cThe first alphabet of products 6aa-6ap refers to the N-(2-iodophenyl)-N-methylmethacrylamide, while the second letter indicates the acetylenes.
Furthermore, to exemplify the utility and tolerance of this green
one-pot domino [Pd]-catalyzed intramolecular Heck and
subsequent Sonogashira coupling, it was extended to the reaction
between ortho-iodophenyl allyl ethers 4a-4g and terminal
acetylenes 2a-2p, using standard microwave conditions.
Delightfully, as anticipated, the protocol was smooth and afforded
the desired dihydrobenzofurans 7aa-7cp, in very good to near
quantitative yields (Table 4). Significantly, the method was
amenable to a wide range of allyl ethers. For example, suitable
for simple to alkyl substituted aromatic rings of allyl ether (7aa-
7dh, Table 4). Notably, amenable to electron deactivating F, Cl
and Br substituents of the allyl ether (7ea-7ga, Table 4). On the
other hand, the reaction was quite smooth with various aryl
acetylenes and showed excellent functional group tolerance.
Particularly, the reaction was smooth with acetylenes containing
protecting group free reactive –NH2 and –COOH groups on the
aromatic ring of the acetylene (7be, 7ce & 7cf, Table 4). Also,
successful with heteroaryl acetylene 2g and bromoaryl acetylene
2d (7ad, 7ag & 7cg, Table 4). In addition, the reaction was quite
successful with terminal aliphatic acetylenes. For example, well
suited with cyclopropyl acetylenes and furnished the
dihydrobenzofuran products, in very good to excellent yields (7ah,
7dh, 7eh & 7fh, Table 4). Remarkably, successful with free
hydroxyl group containing acetylenes (7co, Table 4). In addition,
coupling of ortho-iodophenyl allyl ether 4c with steroidal acetylene
2p was smooth and afforded 7cp, as a diastereomeric mixture.
The plausible reaction mechanism for the synthesis of
heterocyclic products 5/6/7 is as depicted in Scheme 1. Insertion
of Pd0 catalyst across the C(sp2)-I bond of iodoarene of 1/3/4,
furnishes the corresponding aryl-PdII species A. Intramolecular
Heck reaction of A, gives the bicyclic alkyl-PdII species B. Now,
the intermediate B undergoes -coordination with terminal
acetylene 2 and affords the complex C. Then the -complex C
transforms into the -complex D via the elimination of hydroiodic
acid (HI). Finally, reductive elimination via Sonogashira coupling,
leads to the formation of desired heterocyclic products 5/6/7 and
regenerates the Pd0 catalyst and thus completes the catalytic
cycle.
Table 4: Synthesis of dihydrobenzofurans 7aa-7cp from 1-iodo-2-((2-methylallyl)oxy)benzene 4a-4g and terminal alkynes 2a-2p.a,b,c
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aReaction conditions: 1-iodo-2-((2-methylallyl)oxy)benzene 4a-4g (0.25 mmol), acetylenes 2a-2p (0.37 mmol), Pd2(dba)3 (1 mol%), DBU (1,8-
Diazabicyclo[5.4.0]undec-7-ene)(3 equiv), and solvent Water (0.5 mL), 100 C, 15 minutes. bYields in the parenthesis are chromatographically isolated pure products.
cThe first alphabet of products 7aa-7cp refers to the ortho-iodophenyl allyl ether, while the second letter indicates the acetylenes.
free amino, hydroxyl and carboxylic acid functionalities, and
afforded the products, in very good to near quantitative yields.
Acknowledgement
We are grateful to the Department of Science and Technology-
Science and Engineering Research Board (DST-SERB)
[No.SB/S1/OC-39/2014], New Delhi, for financial support. K.R.
and S.B. thank MHRD, New Delhi, for the award of a research
fellowship.
Keywords Microwaves. Domino. Pd-catalysis. 3,3’-Disubstituted
Heterocycles.
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10.1002/ejoc.201800155
European Journal of Organic Chemistry
COMMUNICATION
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Karu Ramesh, [a] Suchand Basuli [a] and
Gedu Satyanarayana*[a]
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Microwave Assisted Domino [Pd]-
Catalysis in Water: A Diversified
Synthesis of 3,3’-Disubstituted
Heterocyclic Compounds
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