Multicomponent Synthesis of Isoindolinone Frameworks via RhIII-Catalysed in situ Directing Group-Assisted Tandem Oxidative Olefination/Michael Addition

Article abstract of DOI:10.1002/asia.201800120

A Rh^III-catalysed three-component synthesis of isoindolinone frameworks via direct assembly of benzoyl chlorides, o-aminophenols and activated alkenes has been developed. The process involves in situ generation of o-aminophenol (OAP)-based bidentate directing group (DG), Rh^III-catalysed tandem ortho C?H olefination and subsequent cyclization via aza-Michael addition. This protocol exhibits good chemoselectivity and functional group tolerance. Computational studies showed that the presence of hydroxyl group on the N-aryl ring could enhance the chemoselectivity of the reaction.

Full text of DOI:10.1002/asia.201800120

CHEMISTRY
AN ASIAN JOURNAL
www.chemasianj.org
Accepted Article
Title: Multicomponent Synthesis of Isoindolinone Frameworks via
Rh(III)-Catalysed in situ Directing Group Assisted Tandem
Oxidative Olefination/Michael Addition
Authors: Liang Wang, Xi Liu, Jian-biao Liu, Jun Shen, Qun Chen, and
Ming-yang He
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10.1002/asia.201800120
Chemistry - An Asian Journal
COMMUNICATION
Multicomponent Synthesis of Isoindolinone Frameworks via
Rh(III)-Catalysed in situ Directing Group Assisted Tandem
Oxidative Olefination/Michael Addition
Liang Wang,a* Xi Liu,a Jian‐biao Liu,b Jun Shen,a Qun Chena and Ming‐yang Hea*
Abstract:
A
Rh(III)-catalysed three-component synthesis of
a),[2] hydroxyl group activation followed by nucleophilic
displacement (Scheme 1, b),[3] base-catalysed tandem
aldol/cyclization reaction (Scheme 1, c),[4] intramolecular aza-
conjugate addition (Scheme 1, d),[5] and tandem C-H
olefination/Michael addition (Scheme 1, e).[6] While
acknowledging these pioneering work in this field, the reported
procedures a~d always suffered from the use of toxic reagents,
tedious synthetic routes, or harsh reaction conditions. In most
cases, the starting materials were not readily available. By
contrast, route e which involved the direct C-H olefination
followed by intramolecular aza-Michael addition should be a
good alternative.[7] However, there are still some challenges to
be addressed. Firstly, cumbersome operations are usually
required for installation or removal of the DGs. Secondly,
limited variability of the introduced DGs also remain as issues
requiring further improvement. Finally, the C-H activation of N-
aryl benzamides may be complicated since both arene C-H
bonds on the C-aryl ring and N-aryl ring could be
cleavaged.[6d,8]
isoindolinone frameworks via direct assembly of benzoyl chlorides,
o-aminophenols and activated alkenes has been developed. The
process involves in situ generation of o-aminophenol (OAP)-based
bidentate directing group (DG), Rh(III)-catalysed tandem ortho
C−H olefination and subsequent cyclization via aza-Michael
addition. This protocol exhibits good chemoselectivity and
functional group tolerance. Computational studies showed that the
presence of hydroxyl group on the N-aryl ring could enhance the
chemoselectivity of the reaction.
Isoindolinone
derivatives
are
important
heterocyclic
compounds owing to their ubiquitous structures in natural
products and pharmaceuticals.[1] For example, Taliscanine,
Nuevamine and Pazinaclone have shown a wide range of
biological properties including antihypertensive, antipsychotic,
anti-inflammatory, and antiviral activities (Figure 1).
Particularly, some biologically active compounds with general
formula I possess anxiolytic and sedative activity. Thus, the
development of efficient methodologies to access such
heterocyclic scaffolds is of great importance.
Figure 1. Selected biologically active isoindolinones.
Literatures on existing approaches toward the synthesis
of compond I include palladium-catalysed three-component
carbonylation/amination/Michael addition process (Scheme 1,
[a]
[b]
Dr. L. Wang, Miss J. Shen, Miss X. Liu, Prof. Q. Chen and Prof. M.
He
School of Petrochemical Engineering, Jiangsu Key Laboratory of
Advanced Catalytic Materials & Technology, Changzhou University,
Changzhou 213164, P. R. China; Fax: +86 519 86330251;
E-mail: lwcczu@126.com;hemingyangjpu@yahoo.com
Dr. J. Liu
College of Chemistry, Chemical Engineering and Materials Science,
Collaborative Innovation Center of Functionalized Probes for
Chemical Imaging in Universities of Shandong, Institute of Molecular
and Nano Science, Shandong Normal University, Jinan 250014, P.
R. China
Scheme 1. Synthetic approaches for preparation of isoindolinone I.
In past decades, some strategies including traceless
DG,[9] deciduous DG,[10] transient DG,[11] and in situ DG[12]
have been conceived and accomplished to address above
issues. Especially, domino C-H activation reactions via in situ
generation of a DG made these processes more simple and
atom-efficient. Just recently, Wan and co-workers reported a
three-component synthesis of o-arylated benzamides by
utilizing o-aminophenol as the DG.[13] Such bidentate DG
Supporting information for this article is given via a link at the end of
the document.
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Table 1. Optimization of reaction conditions.[a]
precursors features not only in the easy availability and low
cost, but also in the direct utility without any prior elaboration.
More importantly, easy variation of the hydroxyl group in the
target products can be realized.
Inspired by these contributions, we envisioned that the
direct assemblies of benzoyl chlorides, o-aminophenol
activated alkenes may provide a step economical approach to
access diverse isoindolinone I. In addition, the hydroxyl group
on the N-aryl ring may enhance the regioselectivity of the
reaction through coordination with the metal catalyst. Notably,
further structural modification of the products can be achieved
through the chemical modification of the hydroxyl group.
Herein, in continuation of our interest in C-H activations,[14] we
disclosed our recent findings in the Rh(III)-catalysed
multicomponent synthesis of isoindolinone frameworks
(Scheme 2).
Entry
Catalyst
Base
Oxidant
Ag2CO3
Solvent
toluene
DMF
Yield(%)[b]
1
2
3
4
5
6
7
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
K2CO3
n.r.
15
17
29
41
69
Ag2CO3
Ag2CO3
DMSO
dioxane
DCE
Ag2CO3
Ag2CO3
Ag2CO3
CH3CN
CH3CN
O
Cu(OAc)2•H2O
85,
O
57[c],22[d]
NH2
[Rh]
R
N
Cl
+
R
+
EWG
8
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
[RhCp*Cl2]2
Pd(OAc)2
K2CO3
K2CO3
K2CO3
K2CO3
Cs2CO3
NaHCO3
NaOH
Et3N
Cu(OTf)2
Ag2O
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
trace
21
Oxidant, Solvent
Temp
OH
HO
EWG
1
3
2
4
9
10
11
12
13
14
15
16
17
18
K2S2O8
n.r.
n.r.
79
Scheme 2. Rh(III)-catalysed multicomponent synthesis of isoindolinones.
O2
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Cu(OAc)2•H2O
Initially, benzoyl chloride (1a), OAP (2) and methyl
acrylate (3a) were selected as the model substrates to
optimize the reaction conditions (Table 1). As shown from the
results, tentative reaction in toluene led to the failure of the
reaction (entry 1). Low yields were obtained in solvents such
as N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO),
dioxane, and 1,2-dichloroethane (DCE) (15~41%, entries 2~5).
Encouragingly, switching the solvent to acetonitrile provided
the desired product 4a in 69% yield (entry 6). Different
oxidants were then examined and Cu(OAc)2•H2O turned out to
be the optimal (85% yield, entry 7). It was worth noting that the
employment of additive such as AgSbF6 and AgBF4 gave
inferior yeilds and C-H olefination on N-aryl ring was also
observed. Substitution of Cu(OAc)2•H2O with Cu(OTf)2 gave
only trace amount of the product, indicating that OAc- might be
necessary for the reaction. Other oxidants including Cu(OTf)2,
Ag2O, K2S2O8 and oxygen gave rather poor yields (entries
8~11). Further investigation in screening the base additives
using K2CO3, Cs2CO3, NaHCO3, NaOH and Et3N proved that
K2CO3 was the best choice (entries 12~15). Among the
surveyed catalysts, Pd(OAc)2 and [RuCl2(p-Cymene)]2 were
not effetive for this transforamtion, while only 32% yield of the
corresponding product was obtained in the presence of
[{Rh(cod)Cl}2] (entries 16~18). Finally, results showed that only
moderate yield was obtained at 80 oC, and no obvious change
in the yield was observed when the reaction was carried out at
a higher temperature (entry 19).
14
23
26
K2CO3
K2CO3
K2CO3
n.r.
32
[{Rh(cod)Cl}2]
[RuCl2(p-
Cymene)]2
trace
19
[RhCp*Cl2]2
K2CO3
Cu(OAc)2•H2O
CH3CN
45[e], 81[f]
[a] Reaction conditions: mixture of 1a (0.3 mmol), 2a (0.3 mmol) and base
(0.9 mmol) in solvent (2 mL) was stirred for 2 h; then 3a (0.45 mmol),
catalyst (5 mol%), and oxidant (0.6 mmol, 2 equiv.) were added, and the
reaction mixture was further stirred overnight at 110 oC. [b] Isolated yields.
[c] AgSbF6 (20 mol%) as the additive. [d] AgBF4 (20 mol%) as the additive.
[e] Reaction at 80 oC. [f] Reaction at 120 oC
(3a) smoothly to provide the corresponding products in good
yields (80~91%). Functional groups such as methyl, tert-butyl,
methoxyl, fluoro, chloro, bromo, and trifluoromethyl survived
the reactions well to afford the desired products in excellent
yields. Notably, the C-halo bonds in the products 4e~4g were
not affected and no Heck coupling byproducts were detected,
enabling the further functionalization of the initial products.
However, p-nitrobenzoyl chloride was not compatible for this
reaction system, and some unknown byproducts were
detected. The steric hindrance showed negligible influence on
the reaction, and substrate 1j successfully delivered product 4j
in 88% yield. Interestingly, evaluation on the substrates 1k and
With the optimized conditions in hand, a series of
benzoyl chlorides were employed to explore the generality of
this protocol (Table 2). Generally, most of the investigated
benzoyl chlorides coupled with OAP (2) and methyl acrylate
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Table 3. Reaction scope for alkenes.[a]
1l showed that these reactions occurred selectively at the less
hindered site. By contrast, extension of this protocol to
heteroaryl benzoyl chlorides turned out to be unsuccessful
under the standard conditions. No reaction occurred when 1m
was employed as the substrate and only olefinated product
was obtained for substrate 1n (4n, 47%).
Table 2. Reaction scope for benzoyl chlorides.[a]
O
O
HO
HO
O
HO
N
N
N
COOMe
COOMe
COOMe
4a, 85%
4b, 90%
4c, 86%
O
HO
O
HO
O HO
N
N
N
MeO
F
Cl
COOMe
COOMe
COOMe
[a] Reaction conditions: mixture of 1a (0.3 mmol), 2a (0.3 mmol) and K2CO3
(0.9 mmol) in CH3CN (2 mL) was stirred for 2 h; then 3 (0.45 mmol),
[RhCp*Cl2]2 (5 mol%), Cu(OAc)2•H2O (0.6 mmol, 2 equiv.) and CH3CN (1 mL)
were added, and the reaction mixture was further stirred overnight at 110 oC;
isolated yields.
4e, 82%
4f, 83%
4d, 91%
O
HO
O
HO
O
HO
N
N
N
O2N
Br
F3C
COOMe
COOMe
COOMe
4g, 81%
4h, 80%
4i, unknow compounds
O
O
HO
O
HO
HO
MeO
N
N
N
COOMe
COOMe
COOMe
4j, 88%
4k, 85%
4l, 83%
O
HO
O HO
HN
O
N
N
COOMe
COOMe
4m, n.r.
4n, 47%
[a] Reaction conditions: mixture of 1 (0.3 mmol), 2a (0.3 mmol) and
K2CO3 (0.9 mmol) in CH3CN (2 mL) was stirred for 2 h; then 3a (0.45
mmol), [RhCp*Cl2]2 (5 mol%), Cu(OAc)2•H2O (0.6 mmol, 2 equiv.) and
CH3CN (1 mL) were added, and the reaction mixture was further stirred
overnight at 110 oC; isolated yields.
A series of alkenes were then examined and the results
were summarized in Table 3. Olefins including methyl acrylate,
methyl methacrylate, ethyl acrylate, n-butyl acrylate, tert-butyl
acrylate and benzyl acrylate readily participated in this reaction,
affording the corresponding products in good to excellent
yields (80~93%). It was worth noting that reaction of
acrylonitrile also proceeded smoothly to give the
corresponding product 4s in 80% yield, which enabled the
further modification of isoindolinone frameworks. We also tried
the reaction of methyl methacrylate, however, no desired
product 4t was observed, probably due to the steric effect.
Finally, electron-neutral olefin such as styrene was checked
and no reaction was observed.
Scheme 2. Control experiment and isotope effect experiment.
Some control experiments were then conducted to get
some insight into the reaction mechanism (Scheme 2).
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Initially, competition reactions were performed with a
series of benzamides. When an equimolar amount of substrate
5 and 6 were subjected to the standard reaction conditions
with a single equivalent of 3a, the reaction favored the
formation of product 4h which was derived from the more
to generate 5-membered rhodacycle B. Then, insertion of an
alkene leads to seven-membered rhodacycle C. Subsequent
β-H elimination releases intermediate D, which undergoes
intramolecular aza-Michael addition to generate the final
product 4a. The RhI cation is oxidized back to RhIII by copper
acetate to complete the catalytic cycle.
electron-deficient
benzamide.
However,
when
such
competition experiment was conducted between substrate 7
and 6, the products were formed in nearly equal amounts.
These results suggested that the Michael reaction could not be
the turnover limiting step for the catalytic cycle. Moreover,
when a 1:1 mixture of 8 and d5-8 was subjected to the reaction,
a significant kinetic isotope effect (kH/kD = 2.9) was observed
(See Supporting information). This indicated that the C–H
bond cleavage was involved in the rate-determining step.
Finally, in order to better explain the good chemoselectivity of
this reaction, substrates 9 and 10 were prepared and coupled
with methyl acrylate 3a. Although these reactions could
provided the target products, considerable C-H olefination
byproducts on the N-aryl ring of the benzamides were also
detected, indicating that the presence of hydroxyl group on the
N-aryl ring greatly enhance the chemoselectivity of the
reaction.
In addition, a computational study was performed (Figure
1, also see Supporting information). As shown in Figure 1,
among the three possible intermediates, the intermediate b is
4.1 and 7.7 kcal/mol more stable respectively than
intermediates a and c, which should be attributed to the
significant C-H/ interactions between Cp* ring and the phenyl
rings.[15] The function of hydroxyl group on the N-aryl ring was
speculated to stabilize the intermediate during the N-
metalation process (See intermediate A in Scheme 3).
Scheme 3. Proposed mechanism.
In summary,
a
Rh(III)-catalysed three-component
synthesis of isoindolinone frameworks via direct assembly of
benzoyl chlorides, o-aminophenols and activated alkenes has
been developed. A series of benzoyl chlorides and activated
alkenes were well tolerated, affording the corresponding
products in good to excellent yields. In most cases, excellent
chemoselectivity was observed. It was assumed that the in situ
generated o-aminophenol (OAP)-based bidentate directing
group could stabilize the intermediate during the N-metalation
and C-H activation process, which was consistent with the
computational study. Notably, potential application of the
target compounds was also exciting. The –OH group could be
readily transformed to other functional groups via conventional
organic reactions.
Cp*
O
Rh
*Cp
O
Rh
O
N
OH
N
Rh
Cp*
b
N
OH
OH
a
c
Relative free energies
(kcal/mol)
7.7
0.0
4.1
Experimental Section
General procedure for the synthesis of compound 4
In a 10 mL reaction vial equipped with a stir bar was charged with 1
(0.3 mmol), 2a (0.3 mmol) and K2CO3 (0.9 mmol) and CH3CN (2 mL).
The mixture was stirred for 2 h. After that, 3 (0.45 mmol), [RhCp*Cl2]2
(5 mol%), Cu(OAc)2•H2O (0.6 mmol, 2 equiv.) and CH3CN (1 mL) were
added, and the reaction mixture was further stirred overnight at 110 oC.
After reaction, the mixture was cooled to room temperature and 10 mL
water was added. After extraction with ethyl acetate (3 × 10 mL), the
combined organic phase was dried over Na2SO4, and the solvent was
removed under reduced pressure. The residue was purified by silica
gel chromatography to afford the desired product 4.
Figure 1. Possible structures of intermediates.
In light of these experiments, a plausible catalytic cycle
was proposed (Scheme 3). Initially, the rhodium dimer
precatalyst exchange ligands to form an acetate-ligated
species with the copper acetate,[8a] which coordinates with in
situ formed N-aryl benzamide to initiate N-metalation. A stable
5-membered rhodacycle A is formed with the assistance of
hydroxyl group. A chemoselective C-H activation then occurs
Selected characterization data
4a: Light yellow solid; 1H NMR (300 MHz, CDCl3) δ 8.33 (s, 1H), 7.91
(dd, J = 4.5, 4.0 Hz, 1H), 7.65 – 7.58 (m, 1H), 7.58 – 7.49 (m, 2H), 7.25
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10.1002/asia.201800120
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COMMUNICATION
– 7.15 (m, 2H), 7.09 (dd, J = 8.1, 1.4 Hz, 1H), 7.00 – 6.95 (m, 1H), 5.65
(dd, J = 8.4, 4.2 Hz, 1H), 3.59 (s, 3H), 2.84 (dd, J = 16.2, 4.3 Hz, 1H),
2.52 (dd, J = 16.2, 8.4 Hz, 1H). 13C NMR (75 MHz, CDCl3) δ 170.6,
168.2, 152.2, 145.2, 132.6, 130.7, 129.0, 128.7, 124.8, 124.3, 124.1,
122.6, 120.9, 120.2, 58.7, 52.0, 36.9. HRMS (ESI): Calcd for
C17H15NNaO4 (M + Na)+ 320.0893, found 320.0899.
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We gratefully acknowledge financial support from the National
Natural Science Foundation of China (21302014 and
21676030), the Jiangsu Key Laboratory of Advanced Catalytic
Materials and Technology (BM2012110), the Priority Academic
Program Development (PAPD) of Jiangsu Higher Education
Institutions, and the Advanced Catalysis and Green
Manufacturing Collaborative Innovation Center of Changzhou
University of Changzhou University.
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Keywords: Isoindolinones • C-H activation • Rh(III) catalysis •
Multicomponent synthesis • Chemoselectivity
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10.1002/asia.201800120
Chemistry - An Asian Journal
COMMUNICATION
Entry for the Table of Contents
COMMUNICATION
Liang Wang,a* Xi Liu,a Jian-biao Liu,b
Jun Shen,a Qun Chena and Ming-yang
Hea*
Page No. – Page No.
Multicomponent Synthesis of
Isoindolinone Frameworks via Rh(III)-
Catalysed in situ Directing Group
Assisted Tandem Oxidative
A Rh(III)-catalysed three-component, chemoselective synthesis of isoindolinone
frameworks via direct assemblies of benzoyl chlorides, o-aminophenols and
activated alkenes has been developed.
Olefination/Michael Addition
This article is protected by copyright. All rights reserved.