A highly efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides

Article abstract of DOI:10.1039/c4cc06457g

An efficient Pd-catalyzed decarboxylative ortho-arylation of amides with aryl acylperoxides was developed. A variety of anilides reacted with aryl acylperoxides to afford the corresponding ortho-arylation products, and N-methoxyarylamides generated phenanthridinones. This journal is

Full text of DOI:10.1039/c4cc06457g

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A highly efficient Pd-catalyzed decarboxylative ortho-
arylation of amides with aryl acylperoxides
Dengke Li,a Ning Xu,a Yicheng Zhang,a and Lei Wang*a,b
Cite this: DOI: 10.1039/x0xx00000x
Received 00th xxxx 2014,
Accepted 00th xxxx 2014
DOI: 10.1039/x0xx00000x
www.rsc.org/
An efficient Pd-catalyzed decarboxylative ortho-arylation of
amides with aryl acylperoxides was developed. A variety of
anilides reacted with aryl acylperoxides to afford the
corresponding
ortho-arylation
products,
and
N-
methoxyarylamides generated phenanthridinones.
During the past decades, the transitionꢀmetalꢀcatalyzed
functionalization of C–H bonds has emerged as a powerful tool
in organic synthesis. Many versatile and flexible methodologies
have been made to activate C–H bonds, in particular aromatic
ones for the synthesis of complicated natural products, drugs
and advanced materials from simple and commercially
available chemicals.1 With the assistance of an orthoꢀposition
directing group in C–H activation, a highly efficient and regioꢀ
selective functionalization could be achieved.2 A wide variety
of functional groups,3−9 such as anilides,3 amides,4
pyridines/quinolones,5 oximes,6 carboxylic acids,7 ketones,8
Nꢀ
methoxy amides,9 have been developed as directing groups.
Among them, directed orthoꢀarylation to construct biaryl
skeleton has gained significant attention because the biaryl
linkages constitute a valuable class of important structural
units.10 It showed that Ru, Rh, Pd, Cu or other transition metal
complexes are efficient catalysts for the direct arylation of
aromatic C–H bonds using arenes which are functionalized with
boron, halides or other organometals.11 However, their
relatively high price and complicated preparation would reduce
their potential applications in organic synthesis.
Scheme 1. Directing-group assisted decarboxylative C–H arylations
Goossen,13 Forgione,14 Myers,15 Liu and Fu,16 Su,17 et al 18
.
However, high reaction temperature and long reaction time
could not be avoided in most cases.
In 2009, Yu demonstrated a direct decarboxylative ortho
ꢀ
arylation of 2ꢀphenylpyridines with benzoyl peroxides in the
presence of a Pdꢀcomplex with good reactivity and selectivity
for the synthesis of arylated derivatives.19 It is the first
utilization of directing groups in decarboxylative crossꢀ
coupling using a peroxide as substrate (Scheme 1).20,21 In our
continuing efforts on the sp2 C−H activation using directing
groups to construct C−C bonds,22 herein, we will report that Pdꢀ
catalyzed direct arylation of anilides using aryl acylperoxides
afforded the corresponding orthoꢀarylation products, and the
Most recently, the utilization of nonꢀtoxic and low cost
carboxylic acids for decarboxylative arylations is an attractive
development in this area.12 It accesses reactive organometallic
intermediates through the removal of CO2 without using
prefunctionalized substrates comparing to traditional crossꢀ
coupling methods. The representative examples of
decarboxylative arylation crossꢀcouplings are developed by
reaction of
Nꢀmethoxyarylamides with aryl acylperoxides
generated the phenanthridinones (Scheme 1).
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In our initial study, we focused on
Nꢀphenylpivalamide
1a), shown relatively high reactivity,3b and benzoyl peroxide
Pd(OAc)2 (7.5 mol%)
H
O
(
(
H
N
R2
TfOH (2.0 equiv)
H
N
O
2a) as the model substrates to screen the optimal reaction
conditions. Treatment of 1a with 2a in the presence of
R2
o
O
+
3A MS, CH3CN
- CO2
O
O
O
2a
3
1
Pd(OAc)2 (7.5 mol%) and TfOH (2.0 equiv) in CH3CN (2.0
o
mL) at 80 C for 32 h, providing the desired product 3a in 53%
yield (Table S1, ESI†). It is noteworthy that the yield of 3a
could be improved to 77% significantly, when activated 3Å
molecular sieves was added to the reaction, but 4Å molecular
sieves was inferior.7c To optimize the reaction conditions,
various additives, temperature and solvents were examined.
Our investigation indicated that no desired product was
obtained when the model reaction was performed in the
absence of TfOH or in the presence of a base, such as K2CO3 or
NEt3 (Table S1, ESI†), and TfOH is crucial for the
reaction.23,3a,8c Other acids including TFA, HOAc, and pivalic
H
H
N
H
H
N
N
N
O
O
O
O
3d, 65%
3c, 50%
3b, 66%
3a, 77%
N
H
N
O
N
N
O
O
3g, N.D.
3f, N.D.
3e, 69%
Scheme 2. Palladium-catalyzed decarboxylative ortho-arylation of N-
substituted anilides with benzoyl peroxide [Reaction conditions:
(0.25 mmol), 2a (0.40 mmol), Pd(OAc)2 (7.5 mol%), TfOH (2.0 equiv),
acid were also surveyed, but they were all ineffective. When pꢀ
1
TsOH and CH3SO3H were used in the model reaction, 3a was
obtained in 31% and 35% yields, respectively. It was also found
that the optimized amount of TfOH is 2.0 equiv. The reaction
temperature and time were also examined and the reaction
activated 3Å MS (70 mg), CH3CN (2.0 mL), air, 80 oC, 32 h]
o
generated the desired product in highest yield at 80 C for 32 h.
The control experiments also showed that the reaction did not
proceed in the absence of Pd and the Pd amount was found to
be 7.5 mol%. Use of other Pdꢀcatalysts, such as Pd(TFA)2,
PdCl2, Pd(PPh3)2Cl2, Pd(PPh3)4 led to the lower yields of 3a
compared with Pd(OAc)2. In addition, the effect of solvent was
explored. Toluene, DCE, 1,4ꢀdioxane, DMF, DMSO, DME or
HOAc/CH3CN were employed instead of CH3CN, poor yields
of 3a were observed (Table S1, ESI†). Therefore, the optimized
reaction conditions were Pd(OAc)2 (7.5 mol%), TfOH (2.0
equiv) and 3Å molecular sieves in CH3CN at 80 oC for 32 h.
With the optimized reaction conditions in hand, the effect of
N
ꢀsubstituents on the anilides including acetanilide (1b),
phenylbutyramide 1c), ꢀphenylbenzamide 1d), 1ꢀ
phenylpyrrolidinꢀ2ꢀone (1e), ꢀacetylꢀ2,3ꢀdihydroindole (1f
Nꢀ
(
N
N
(
)
and 1,1ꢀdimethylꢀ3ꢀphenylurea (1g) was studied and the results
are shown in Scheme 2. Gratifyingly, most of them reacted with
2a to generate the corresponding products (3b−3e) in 50−69%
yields. However, 1f and 1g failed to react with 2a. It showed
that pivalanilide was the best one for the arylation.
Under the optimized reaction conditions, the substrate scope
of
investigated to illustrate the efficiency of this strategy (Scheme
3). ꢀArylpivalamides with various substituents (Me, ꢀPr,
Nꢀarylpivalamides (1) and aryl acylperoxides (2) was
N
i
OMe, F, Cl, Br) on the benzene rings were explored.
Pivalamides bearing electronꢀdonating groups at metaꢀ and/or
paraꢀpositions of the phenyl rings (1h
underwent the decarboxylative orthoꢀarylation smoothly to
generate the corresponding products (3h 3i 3k 3l and 3p
Scheme 3) in 61 81% yields. An obvious orthoꢀsubstituent
effect was observed in the reaction of 2ꢀmethyl substituted
pivalamide 1j with 2a 3a,9b
However, the substrates bearing
, 1i, 1k, 1l and 1p)
Scheme 3. The scope of Pd-catalyzed decarboxylative ortho-arylation
of anilides with aryl acylperoxides [Reaction conditions: 1 (0.25 mmol),
,
,
,
,
2
(0.40 mmol), Pd(OAc)2 (7.5 mol%), TfOH (2.0 equiv), activated 3Å MS
−
o
a
(70 mg), CH3CN (2.0 mL), air, 80 C, 32 h; With K2S2O8 (2.0 equiv) at
130 oC for 32 h]
.
electronꢀwithdrawing groups (3ꢀF, 3ꢀCl, 3ꢀBr) reacted with 2a
under the standard reaction conditions, but failed. When the
reactions were performed with addition of K2S2O8 (2.0 equiv)
acylperoxides underwent the coupling with 1i smoothly, giving
the coupling products 3r–3u, 3w and 3x in 55–75%, 59% and
47% yields, respectively. An orthoꢀsubstituent effect was also
found during the formation of 3v in 36% yield. However,
at 130 oC, the desired orthoꢀarylation products (3m
,
3n, and 3o
)
were obtained in 33
was instead of 1ꢀnapthyl (1q), it provided 3q in 50% yield.
To further expand the substrate scope, we performed the
present arylation of ꢀ( ꢀtolyl)pivalamide (1i) with a variety of
aryl acylperoxides (2b 2j), and the results are also shown in
−
41% yields. Whereas the phenyl ring in
1
neither the strong electronꢀwithdrawing (
pꢀNO2) nor the strong
electronꢀdonating group ( ꢀCH3O) could be functionalized to
p
generate the desired product in the reaction with starting
materials unchanged and recovered (3y and 3z).
With the obtained 3b in hand, its transformation through an
intramolecular cyclization under Buchwald amination conditions
was examined, providing carbazole 4b in 91% yield (Scheme 4).24
N
m
–
Scheme 3. Substituted groups, such as 4ꢀmethylꢀ, 4ꢀfluoroꢀ, 3ꢀ
chloroꢀ, 4ꢀchloroꢀ, 4ꢀbromoꢀ, and 4ꢀtertꢀbutylphenyl
2 | J. Name., 2014, 00, 1-3
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generated through chelateꢀdirected C−H activation of Nꢀ
phenylpivalamide (1a) with the assistance of TfOH. Meanwhile,
phenyl radical produced in situ by the thermal decomposition of
benzoyl peroxide (2a) along with release of CO2, reacted with
intermediate I to realize the oxidation of Pd(II) to dimeric Pd(III) or
Pd(IV) (intermediate II).25 Finally, Pd(II) species was regenerated
through the reductive elimination of II, with providing the desired
product 3a. When the radical scavengers, such as TEMPO (2,2,6,6ꢀ
tetramethylpiperidylꢀ1ꢀoxyl) and ascorbic acid were added up to 1.0
equiv in the reaction, no desired product was observed, suggesting
the reaction may be undergo a radical process (Table S3, ESI†).
Scheme 4. Synthesis of carbazole via Buchwald amination
Subsequently, other amide substrates were carried out for the
purpose of broadening the application of current methodology. A
series of amides, such as benzamide, Nꢀisoꢀpropylbenzamide, Nꢀ
tosylbenzamide were used for the reaction with benzoyl peroxide,
but failed. Much to our pleasure, Nꢀmethoxybenzamide (5a) was
found to be a promising coupling partner in the reaction, providing
an arylationꢀcyclization product phenanthridinone (6a), as an
important structural motif in numerous biologically molecules, in
oneꢀpot with 21% yield (Table S2, ESI†). Further optimization
revealed that a best of reaction conditions is consisted of Pd(OAc)2
(7.5 mol%), TfOH (2.0 equiv) and 4Å molecular sieves in
HOAc/CH3CN (V/V = 1/1) at 80 oC for 24 h.
Using this strategy, a number of phenanthridinone derivatives
could be prepared in moderate to good yields and the results are
summarized in Scheme 5. A variety of Nꢀmethoxyarylamides with
either electronꢀdonating or electronꢀwithdrawing groups, even the
strong electronꢀwithdrawing group (pꢀNO2), on the benzene rings
could be tolerated under the employed reaction conditions, and
afforded the desired products in moderate to good yields. It should
be noted that Nꢀmethoxyarylamides with electronꢀdonating groups
on the benzene rings gave a higher yield than that with electronꢀ
withdrawing groups on the benzene rings (55–62% yields for 6b, 6c,
6g and 6h vs 37–46% yields for 6d, 6e, 6f and 6i). Nꢀ
Methoxyarylamides with an electronꢀdonating group such as methyl
H
N
O
HOAc
TfO
II
O
O
O
H
O
O
2a
1a
Cyclopalladium
H
N
Pd(OAc)2/TfOH
O
O
Pd II
2
I
H
N
CO2
O
H
N
Pd
TfO
O
3a
Scheme 6. A plausible reaction mechanism
In summary,
decarboxylative orthoꢀarylation of amides with aryl
acylperoxides via C H activation and functionalization was
a
highly efficient palladiumꢀcatalyzed
−
(Me), phenyl (Ph), and methoxy (MeO) at the paraꢀ or metaꢀposition developed. This synthetic methodology provides a simple and
of the phenyl rings gave the comparable product yields to nonꢀ
substituted one (Nꢀmethoxybenzamide, 5a). To further expand the
substrate scope, some aryl acylperoxides, including 4ꢀmethylphenyl
direct route to a wide variety of diversely orthoꢀfunctionalized
biaryl compounds from anilides, and phenanthridinones from
Nꢀmethoxyarylamides through an arylationꢀcyclization process.
acylperoxide, 4ꢀchlorophenyl acylperoxide, and 4ꢀbromophenyl The further investigation is currently underway.
acylperoxide, were used to react with 5a, providing the
corresponding products (6j–6l) in 35–57% yields.
This work was financially supported by the National Science
Foundation of China (No. 21172092).
R2
O
Pd(OAc)2 (7.5 mol%)
TfOH (2.0 equiv)
O
O
O
OMe
N
O
OMe
Notes and reference
O
N
N
HOAc/CH3CN = 1/1
+
H
o
O
R1
a
- CO2
4A MS,
R1
R2
H
Department of Chemistry, Huaibei Normal University, Huaibei, Anhui
2
R2
5
6
235000, P R China; Eꢀmail: leiwang@chnu.edu.cn
Tel.: +86ꢀ561ꢀ380ꢀ2069; fax: +86ꢀ561ꢀ309ꢀ0518
O
O
O
OMe
OMe
OMe
OMe
N
N
O
N
b
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of
F
Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R
China
6c, 58%
6d, 42%
6a, 60%
6b, 62%
OMe
O
O
O
OMe
OMe
OMe
†
Electronic Supplementary Information (ESI) available: [details of
N
N
N
N
N
any supplementary information available should be included here]. See
DOI: 10.1039/b000000x/
Cl
Br
Ph
MeO
6h, 55%
6e, 46%
6g, 58%
6f, 43%
O
O
O
O
OMe
OMe
Br
OMe
OMe
Cl
N
N
N
1 (a) Transitions Metals for Organic Chemistry, 2nd ed. (Eds.: M. Beller, C.
Bolm), WileyꢀVCH, Weinheim, 2004; (b) J. A. Labinger and J. E.
Bercaw, Nature, 2002, 417, 507; (c) K. Godula and D. Sames, Science,
2006, 312, 67.
O2N
6k, 38%
6j, 57%
6i, 37%
6l, 35%
Scheme 5. The scope of one-pot Pd-catalyzed decarboxylative reaction
anilides with aryl acylperoxides for the synthesis of phenanthridinones
[Reaction conditions: 5 (0.25 mmol), 2 (0.40 mmol), Pd(OAc)2 (7.5 mol%),
TfOH (2.0 equiv), activated 4Å MS (70 mg), HOAc/CH3CN (V/V = 1/1, 2.0 mL),
air, 80 oC, 24 h]
2
For selected directingꢀgroup assisted CꢀH activation reviews, see: (a) D. A.
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Based on the literatures and our observation,19 a possible reaction
pathway is proposed in Scheme 6 although the mechanism is not
clear. Initially, a sixꢀmembered cyclopalladated intermediate I was
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