Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols

Article abstract of DOI:10.1002/adsc.201801606

A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).

Full text of DOI:10.1002/adsc.201801606

Title: Efficient Synthesis of Functionalized Indene Derivatives via
Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and
Allylic Alcohols
Authors: Lin Dong, Jing Zhang, Jun-Shu Sun, and Ying-Qi Xia
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201801606
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10.1002/adsc.201801606
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Efficient Synthesis of Functionalized Indene Derivatives via
Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and
Allylic Alcohols
Jing Zhang,a Jun-Shu Sun,a Ying-Qi Xia,a and Lin Donga,*
a
J. Zhang, J.-S. Sun, Y.-Q. Xia, Prof. Dr. L. Dong
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, West China School of
Pharmacy, Sichuan University, Chengdu 610041, China
E-mail: dongl@scu.edu.cn
Received: ((will be filled in by the editorial staff))
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/adsc.201######.((Please
delete if not appropriate))
Abstract:
A
highly efficient rhodium(III)-catalyzed
synthesis of novel functionalized indene derivatives has
been achieved via C−H activation/intramolecular aldol
condensation. This cascade reaction is an atom economical
protocol which could be further applied to build more
complex compounds.
Keywords: cascade reaction; indene derivatives;
oxadiazoles; allylic alcohols; rhodium.
Figure 1. Drug candidates bearing indene unit.
The indene units have emerged as an intriguing class
of synthetic skeletons owing to the unique properties
in drug candidates, catalysts and materials science
(Figure 1).[1] Thus, as a privileged scaffold, a number
of approaches used to construct the ring system have
been developed.[2] Despite this progress, more
efficient and simple synthesis methods for these units
have still been pursued and explored by chemists.
Recently, transition-metal-catalyzed C−H bond
functionalization has emerged as versatile protocols
to create various intricate compounds.[3] In particular,
these highly efficient and atom economical strategies
have been widely utilized to prepare the substituted
indene derivatives.[4-6] Li and Glorius have separately
reported novel rhodium(III)-catalyzed cascade
reactions to synthesize indene derivatives of aromatic
ketone derivatives via ortho C−H bond activation/
intramolecular aldol condensation (Scheme 1, eq 1).[5]
On the other hand, metal-catalyzed [3+2] annulations
of ketimines/ketones with alkynes/alkenes have also
been developed to build indene units (Scheme 1, eq
2).[6]
synthesis of functionalized indenes,[8] we envisaged
that the use of 3-aryl-1,2,4-oxadiazoles might
contribute to generate the new indene core derivatives.
In addition, we also hope to use commercially
available allylic alcohols as coupling partners to
study this new synthetic method.[9] Herein, we have
reported the novel reaction to synthesize N-(2-acetyl-
1H-inden-3-yl) acetamide derivatives through
rhodium(III)-catalyzed cascade annulation between
3-aryl-1,2,4-oxadiazoles and allylic alcohols (Scheme
1, eq 3). The protocol involves C−H
activation/intramolecular aldol condensation process,
and the cleavage of the labile N•O bond plays a
crucial role in the internal oxidation mechanism.[10]
1,2,4-oxadiazole core, bearing an N•O linkage in
the heterocyclic ring, has attracted attention due to its
beneficial to achieve an efficient synthesis of
complex frameworks via C−H activation.[7] In
continuation of our research interest in
1
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10.1002/adsc.201801606
Advanced Synthesis & Catalysis
25[c]
26[c]
27[c]
28[c]
[a]
TsOH/1.15
TsOH/1.25
TsOH/1.15
TsOH/1.15
DCE
DCE
DCE
DCE
84
78
Cu(OAc)2H2O/0.3
Cu(OAc)2H2O/0.3
CuOAc/0.3
Scheme 1. Synthesis indene derivatives via C–H activation.
70
78[e], 53[f]
Cu(OAc)2H2O/0.3
We commenced our examination by investigating
the cascade annulation of 5-methyl-3-phenyl-1,2,4-
oxadiazole 1a and but-3-en-2-ol 2a (Table 1).[11] In
Reaction conditions unless otherwise specified: 0.05
mmol of 1a, 5 equiv of 2a, 5 mol % of [Cp*RhCl2]2, 0.5
mL of solvent, 100 °C, 16 h, Ar atmosphere. 1-AdCOOH
is the abbreviation of 1-adamantanecarboxylic acid.
[b] Isolated yield.
.
the presence of [Cp*RhCl2]2 and Cu(OAc)2 H2O,
annulation product 3aa could be obtained in 18%
yield (entry 1). No reaction was observed when base
was added as an additive (entry 2). Various acids
were screened and p-toluenesulfonic acid gave the
relative high effect (entries 3-7). To our surprise, the
higher yield of 3aa could be afforded when the
[c]
5 equiv of 2a stirred for 6 h, then additional 2 equiv of
2a was added for 10 h.
[d] Under air.
[e] 0.3 mmol of 1a.
[f] 3 mmol of 1a.
.
loading of Cu(OAc)2 H2O was decreased to 0.3 equiv
Table 2. Substrate scope of the oxadiazoles.[a]
(entry 8), while only trace product was produced
.
without Cu(OAc)2 H2O (entry 9). Unfortunately, no
improvement was observed by using other copper
sources (entries 10−12). In addition, silver salts were
less effective for this cascade reaction (entries 13−16).
And other solvents also gave inferior results (entries
17–21). To our delight, when 2a was added in two
portions, the yield could be increased, probably
because allylic alcohols could be decomposed in this
reaction system and increasing the starting material
2a during the reaction process would make the
reaction proceed more smoothly (entry 22). While the
yield of product would be decreased under the air
condition (entry 23). Notably, the loading of TsOH
was very critical, 1.15 equiv of TsOH was proved to
give the best results (entries 24–26). In addition,
CuOAc as an additive gave rise to a lower yield
(entry 27). Increasing scale of 1a might slightly
reduce the yield of the reaction (entry 28).
Table 1. Optimization of the reaction conditions.[a]
Yield[b]
%
/
Entry
Additive/[equiv]
Acid/[equiv]
Solvent
1
2
3
4
5
6
7
8
-
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DME
TFE
18
trace
24
22
37
25
29
56
trace
51
52
trace
34
trace
trace
trace
52
trace
23
trace
trace
74
62
50
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/2
Cu(OAc)2H2O/0.3
--
Cu(acac)2/0.3
Cu(OAc)2/0.3
Cu(OTf)2/0.3
AgOAc /0.3
NaOAc/1
PivOH/1
1-AdCOOH/1
TsOH/1
CF3COOH/1
HOAc/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/1
TsOH/0.8
[a] Reaction conditions unless otherwise specified: 5 mol %
of [Cp*RhCl2]2, 1.15 equiv of TsOH, 0.5 mL of DCE, 0.05
mmol of 1, 5 equiv of 2a stirred for 6 h, then additional 2
equiv of 2a was added for 10 h, 100 °C, Ar atmosphere.
Isolated yield.
9
10
11
12
13
14
15
16
17
18
19
20
21
22[c]
23[c,d]
24[c]
[b] 0.3 mmol of 1.
[c] 0.5 mmol of 1.
With the optimized reaction conditions established,
AgSbF6/0.3
AgBF4/0.3
AgNTf2/0.3
the scope of oxadiazoles was explored (Table 2).[11]
A
broad of electron-donating and -withdrawing
substituents at the para positions of the benzene ring
were compatible, affording the corresponding
products (3ba-3ha) in good yields. In addition, meta-
substituted oxadiazoles 1i and 1j occurred smoothly
but giving a mixture of regioisomers. In contrast,
Cu(OAc)2H2O/0.3
Cu(OAc)2H2O/0.3
Cu(OAc)2H2O/0.3
Cu(OAc)2H2O/0.3
Cu(OAc)2H2O/0.3
Cu(OAc)2.H2O/0.3
Cu(OAc)2.H2O/0.3
Cu(OAc)2H2O/0.3
Dioxane
CH3CN
MeOH
DCE
DCE
DCE
2
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10.1002/adsc.201801606
Advanced Synthesis & Catalysis
meta-methyl substituent 1k showed excellent
regioselectivity. Furthermore, 3la was also obtained
in single isomer. While the steric effect of the ortho-
methyl and halogen substituent influenced the
efficiency dramatically, no corresponding products
were delivered (3ma-3na). Moreover, thiophene
derivatives with electron-withdrawing and -donating
groups were also tolerated in this reaction system but
gave inferior results, probably due to the electronic
effects (3oa-3qa). -Naphthyl-substituted 1r could
not give corresponding product owing to the steric
hindrance, while the -naphthyl-substituted 1s was a
suitable substrate and 3sa was obtained in 68% yield.
In addition, substituents on R2 position of oxazoles
could also be extended to other substituents such as
linear alkyl chains, phenyl and benzyl groups,
affording corresponding products (3ta-3wa) in
moderate to good yields. Unfortunately, 1x carrying
vinylic sp2 C−H bond exhibited negative reactivity
towards the cascade reaction.
better yields (3ai and 3aj) could be obtained when we
replaced TsOH with 1-adamantanecarboxylic acid. In
addition, heteroaryl and naphthyl-substituted allylic
alcohols showed good reactivity, giving the cascade
products in good yields (3ak-3am).
To determine the reaction pathway, deuterium-
labeling experiment and several competition
experiments were performed (Scheme 2). When 1a
was quenched by D2O in the absence of olefins after
4 h, 33% deuterium was observed at both ortho
positions (eq 1). Electron-donating and -withdrawing
substituents at the para positions of the benzene ring
exhibited similar reactivity in the reaction system (eq
2). Furthermore, methyl substituted oxazole was
more beneficial for this cascade reaction than phenyl
one (eq 3).
Table 3. Substrate scope of the allylic alcohols.[a]
Scheme 2.
Deuterium-labelling experiment and
competition experiments.
To demonstrate the synthetic utility of the carbonyl
acetamide structure 3, further transformations were
conducted in Scheme 3. Noticeably, under the
conditions of hydrolysis, the corresponding product 4
could be obtained in 77% yield. In addition, indeno
[1,2-d] pyrimidine was easily synthesized from 3aa
by using NH4OAc.
[a] Reaction conditions unless otherwise specified: 5 mol %
of [Cp*RhCl2]2, 1.15 equiv TsOH, 0.5 mL of DCE, 0.05
mmol of 1a, 5 equiv of 2 stirred for 6 h, then additional 2
equiv of 2 was added for 10 h, 100 °C, Ar atmosphere.
Isolated yield.
[b] 0.5 mmol of 1a.
[c] 2 equiv of 1-adamantanecarboxylic acid.
[d] 0.3 mmol of 1a.
Next, we explored the scope of the reaction with
respecting allylic alcohols as the coupling partners
(Table 3).[11] A series of straight chain alkyl-
substituted allylic alcohols reacted smoothly to
provide the desired products in good yields (3ab-3af).
Cyclic and branched chain substituted allylic alcohols
were also compatible and afforded corresponding
products in 64% and 88% yield, respectively (3ag
and 3ah). Interestingly, -aromatic-substituted allylic
alcohols could not undergo the cross-coupling
reaction under the current reaction conditions, while
Scheme 3. Synthetic application of product 3aa.
Based on mechanistic experiments and literature
reports, a plausible mechanism was proposed in
3
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10.1002/adsc.201801606
Advanced Synthesis & Catalysis
aldol condensation. Furthermore, the novel approach
has good applicability to a broad scope of functional
groups.
Experimental Section
General procedure for synthesis of the Indene
Derivatives: 5-methyl-3-phenyl-1,2,4-oxadiazole 1a (8.0
mg, 0.05 mmol), but-3-en-2-ol 2a (18.0 mg, 0. 25 mmol),
.
[Cp*RhCl2]2 (1.5 mg, 5 mol %), Cu(OAc)2 H2O (3.0 mg,
0.3 equiv) and TsOH (9.9 mg, 1.15 equiv.) were stirred in
DCE (0.5 mL) under argon atmosphere at 100 °C for 6 h,
then additional 0.1 mmol of 2a was added for 10 h. After
completion, the reaction mixture was purified by flash
chromatography eluting with ethyl acetate and petroleum
ether (1:15) to give the product 3aa as a yellow solid (9.0
mg, 84%).
Acknowledgements
We are grateful for the financial support from the NSFC
(21572138) and 111 Project (B18035).
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5
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Advanced Synthesis & Catalysis
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10.1002/adsc.201801606
Advanced Synthesis & Catalysis
COMMUNICATION
Efficient Synthesis of Functionalized Indene
Derivatives via Rh(III)-Catalyzed Cascade
Reaction between Oxadiazoles and Allylic
Alcohols
Adv. Synth. Catal. Year, Volume, Page – Page
Jing Zhang, Jun-Shu Sun, Ying-Qi Xia, and Lin
Dong*
7
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