Copper-Catalyzed Oxidative C?H Bond Functionalization of N-Allylbenzamide for Regioselective C?N and C?O Bond Formation

Article abstract of DOI:10.1002/asia.201900192

Copper-catalyzed oxidative couplings of N-allylbenzamides for C?N and C?O bond formations have been developed through C?H bond functionalization. To demonstrate the utility of this approach, it was applied to the synthesis of β-aminoimides and imides. To the best of our knowledge, these are the first examples in which different classes of N-containing compounds have been directly prepared from the readily available N-allylbenzamides using an inexpensive catalyst/oxidant/base (CuSO₄/TBHP/Cs₂CO₃) system.

Full text of DOI:10.1002/asia.201900192

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Accepted Article
Title: Copper-Catalyzed Oxidative C-H Bond Functionalization of N-
Allylbenzamide for Regioselective C-N and C-O Bond Formation
Authors: Jala Ranjith and Palakodety Radha Krishna
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COMMUNICATION
Copper-Catalyzed Oxidative C-H Bond Functionalization of N-
Allylbenzamide for Regioselective C-N and C-O Bond Formation
Jala Ranjith[a] and Palakodety Radha Krishna*[a]
[a]
Mr. Jala Ranjith, Dr. Palakodety Radha Krishna
Organic Synthesis and Process Chemistry Division
CSIR-Indian Institute of Chemical Technology
Hyderabad-500007, India.
E-mail: prkgenius@iict.res.in
Abstract: Novel copper-catalyzed oxidative couplings of N-
allylbenzamides via C-H bond functionalization for C-N and C-O
bond formations have been developed. To demonstrate the utility of
this approach, it was applied for the synthesis of β-aminoimides and
Imides. To the best of our knowledge, these are the first examples in
which different classes of N-containing compounds were directly
prepared from the readily available N-allylbenzamides using an
inexpensive catalyst-oxidant-base (CuSO4/TBHP/Cs2CO3) system.
an amine source into the corresponding β-aminoimides, using
CuSO4-TBHP as the system. To the best of our knowledge, no
report exists in the literature on these oxidative transformations
(Scheme 1).
The required substrates N-allylbenzamides were readily
prepared from the corresponding benzoyl chloride and
allylamine as per our earlier method.[11] At the outset, N-
allylbenzamide 1a was chosen as the model substrate to
optimize reaction conditions including the oxidant equivalents,
catalyst type, base, solvent, and time as disclosed in Table 1.
Accordingly, a preformed solution of N-allylbenzamide 1a (1.0
equiv), TBHP (70% solution in water, 2.0 equiv) and CuSO4 (2.5
mol %) was dissolved in CH3CN (2 mL) at room temperature.
Then, Cs2CO3 (2.0 equiv) and 1H-benzotriazole (1.0 equiv) as a
nucleophilic amine source was added and the resultant solution
The immense potential of C-H bond activation for organic
transformations using transition metal catalysts has been
realized in robust and efficient methods for C-C, C-O and C-N
bond formations over the decades.[1] Although different transition
metals are known to catalyze the C-H oxidations,[2] among them
copper is particularly advantageous because it is less expensive,
low toxicity with broad tolerance. Recently, the copper catalyzed
C-H oxidations for C(sp)-, C(sp2)- and C(sp3)-X (X = C, N, and
O) bond formations have been described.[3] Also, the direct
functionalization of allylic C-H bond of terminal alkenes has
received a great deal of interest, leading to the frequent
appearance of new protocols.[4] In particular, transition-metal
catalyzed direct difunctionalization of allyl moiety is an important
strategy for the synthesis of complex molecules.[5] In this context,
very recently, Zhao et al. reported nickel-catalyzed 1,3
difunctionalization of allylamine moieties.[6]
was stirred for 10
h at same temperature, the reaction
proceeded to afford the desired product β-aminoimide (2aa) in
low yield (Table 1, entry 1). In order to improve the efficiency, we
studied the amount of CuSO4, to our delight, 10 mol% of catalyst
provided an 89% yield of the desired product 2aa (Table 1,
entries 2, 3 and 4). Moreover, during the optimization study, the
required TBHP was reduced to 1.0 equiv and 1.5 equiv and the
yield of 2aa correspondingly decreased to 52% and 67%
respectively (Table 1, entries 5 and 6). In the absence of the
catalyst no product was formed (Table 1, entry 7). Next, the
replacement of CuSO4 with other catalysts, including CuBr, TBAI,
I2, and NIS resulted in no improvement (Table 1, entries 8, 9, 10
and 11). The replacement of TBHP with m-CPBA and oxone, the
product was undetected (Table 1, entries 12 and 13). In the
absence of the base no product formation was identified (Table
1, entry 14). Also, we optimized the reaction conditions with
various bases such as K2CO3, Na2CO3, and CaCO3 which
resulted in a decreased yield of 2aa (Table 1, entries 15, 16 and
17). Further optimization using other solvents such as CH2Cl2, 1,
2-dichloroethane (DCE), and THF resulted in the formation of
2aa in lower yields (Table 1, entries 18, 19 and 20). Through,
these results we concluded that CuSO4 (10 mol %), TBHP (70%
solution in water, 2.0 equiv) and Cs2CO3 (2.0 equiv) in CH3CN (2
mL) at room temperature are the optimal conditions for the
synthesis of β-aminoimide 2aa (Table 1, entry 4).
Scheme 1. C-H bond functionalization of allylbenzamides.
N-Containing compounds such as imides[7] and triazole[8]
moieties are present in a variety of biologically and medicinally
active compounds, and their synthesis and functionalization
have received great attention. Traditionally, the synthesis of
imides have relied primarily on amides with carbonyl chlorides,
aldehydes, and acetic anhydride.[9] Notwithstanding these
advancements, current trends on imide syntheses focus on the
direct oxidation of sp3 C-H bond adjacent to the nitrogen
atom.[10] Herein we disclose an efficient and practical approach
for the oxidative coupling of N-allylbenzamides with triazoles as
Table 1. Optimization of the reaction conditions[a,b]
.
Catalyst
(mol%)
oxidant
(equiv.)
Base
(2equiv.)
Yield
(%)b
Entry
Solvent
1
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10.1002/asia.201900192
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yield (Scheme 2). Likewise, a range of N-allylbenzamides (1b-e)
and sterically hindered substrates (1g-1i) bearing electronically
varied groups (e.g. OMe, F, Ph, NO2) on the phenyl ring were
found to be tolerant in these transformations, and the
corresponding products (2ab-2eb and 2gb-2ib) were obtained in
moderate to good yields in highly regioselective manner. Further
structural confirmation of 2ca and 2ab was ascertained by X-ray
studies (see SI). Other N-containing nucleophiles did not yield
the respective products.
1
2
CuSO4(2.5)
CuSO4 (5)
CuSO4(7.5)
CuSO4(10)
CuSO4 (10)
CuSO4 (10)
-
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (1)
TBHP(1.5)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
Cs2CO3
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
26
44
76
89
52
67
0
3
4
5
6
Scheme 2. Synthesis of β-amino imides [a,b]
.
7
8
CuBr (10)
TBAI (10)
I2 (10)
38
32
Trase
10
0
9
10
11
12
NIS (10)
m-CPBA
CuSO4 (10)
(2)
13
14
15
16
17
18
19
20
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
CuSO4 (10)
Oxone (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
TBHP (2)
Cs2CO3
-
CH3CN
CH3CN
CH3CN
CH3CN
CH3CN
CH2Cl2
DCE
0
0
2aa, R = H, 89%
2fa = 71%
2ba, R= p-OMe, 93%
2ca, R = 4-F, 83%
2da, R = 2-Ph, 84%
2ea, R = 4-NO2, 66%
K2CO3
Na2CO3
CaCO3
Cs2CO3
Cs2CO3
Cs2CO3
34
Trase
0
2ga, R = H, 91%
2ha, R = OMe, 83%
2ia, R = F, 79%
56
20
0
2ab, R = H, 86%
2bb, R = p-OMe, 90%
2cb, R = 4-F, 86%
2db, R = 2-Ph, 81%
2eb, R = 4-NO2, 71%
THF
2gb, R = H, 84%
2hb, R = OMe, 82%
2ib, R = F, 74%
[a] Reaction conditions: N-allylbenzamide (0.62 mmol), aq. TBHP (1.24 mmol),
CuSO4 (10 mol%), Cs2CO3 (1.24 mmol), benzotriazole (0.6 mmol, 1.0 equiv.),
solvent (2 mL), temperature (rt) under nitrogen atmosphere.
[a] Reaction conditions: 1a (1.0 equiv), CuSO4 (10 mol%), aq. TBHP (2.0
equiv), triazole (1.0 equiv) and Cs2CO3 (2.0 equiv) in CH3CN (2 mL) solvent at
rt. [b] Isolated yield.
[b] Isolated yield.
Having optimized reaction conditions in hand, we
investigated the scope and generality of the oxidative synthesis
of β-aminoimide 2. As illustrated (Scheme 2), all the substrates
1a-i well tolerated the optimized conditions to furnish the
corresponding β-aminoimide derivatives 2 in good to excellent
yields. Interestingly, the reaction shows excellent regioselectivity.
The electron rich substrate p-OMe (1b) also underwent the
reaction to give the desired product 2ba in 93% yield.
Subsequently, we next probed the feasibility of electron-
withdrawing substituent such as (F, Ph, and NO2) 1c-1e on the
phenyl ring. Of note, all the reactions proceeded smoothly,
affording the corresponding β-aminoimide products 2ca-2ea in
66-84% yields. Noteworthy, a heterocyclic bearing allylamide
such as N-allylisonicotinamide 1f performed well under oxidative
coupling process to generate 2fa in 71% yield. Notably, the
oxidative addition reaction of sterically hindered substrate N-
allyl-2-benzamidobenzamide 1g and their substituent such as
methoxy 1h and fluoro 1i moieties are accomplished
successfully to obtain the β-aminoimide derivatives 2ga, 2ha
and 2ia in 91%, 83% and 79% yields respectively.
Figure 1. ORTEP representation of Compound 2ca (CCDC 1837199).
X-ray crystal structure of 2ca showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level and H atoms
are represented by circles of arbitrary radii.
Figure 2. ORTEP representation of Compound 2ab (CCDC 1837198).
X-ray crystal structure of 2ab showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 30% probability level and H atoms
are represented by circles of arbitrary radii.
Interestingly, by switching the nucleophilic amine source to
1,2,4 triazole, oxidative coupling reaction of 1a proceeded
smoothly to afford the corresponding aminoimide 2ab in 86%
2
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Further, N-allylbenzamides 1a treated under optimized
reaction conditions in the absence of nucleophilic amine source,
afforded the corresponding α,β-unsaturated imides 3a in 87%
yield (Scheme 3). While the substrate with an electron-donating
group (-OMe) 1b gave the desired product 3b in 93% yield. N-
allylbenzamides with electron-withdrawing groups such as -F, -
Ph and -NO2, substrates 1c-e were also applied in the reaction
successfully to provide the corresponding imide compounds 3c-
e in 89%, 81% and 73% yields respectively. Further, the new
butoxy radical abstracts an allylic hydrogen of 1a providing allylic
radical A. Single-electron transfer (SET) from A onto the
generated copper (III) species leads to allylic cation B, which
readily undergoes oxidation to yield imine intermediate C. N-
acyliminium intermediate C may succumb to the nucleophilic
addition of TBHP and generate an intermediate 4a. Further,
peroxide 4a converted into the corresponding imide 3a by
Cs2CO3 via Kornblum-DeLaMare rearrangement.[13] Finally,
Michael addition of 3a with triazole nucleophile gave the desired
product 2aa.
series
of
sterically
hindered
substrate
N-allyl-2-
benzamidobenzamides 1g, 1h and 1i proceeded smoothly to
afford the corresponding products 3g, 3h and 3i in good yields
effectively. Noteworthy that N-benzylbenzamide 1j also afforded
product 3j in good yield 89%.
Scheme 4. Control experiments.
Scheme 3. Synthesis of N-Acryloylbenzamides [a,b]
.
3g, R = H, 82%
3h, R= OCH3,88%
3i, R = F, 84%
3a, R = H, 87%
3b, R = p-OCH3, 93%
3c, R = 4-F, 89%
3d, R = 2-Ph, 81%
3e, R = 4-NO2,73%
Scheme 5. Proposed Mechanism.
3j, 89%
[a] Reaction conditions: 1a (1.0 equiv), CuSO4 (10 mol%), aq. TBHP (2.0
equiv) and Cs2CO3 (2.0 equiv) in CH3CN (2 mL) solvent at rt.
[b] Isolated yield.
To gain insight into the mechanism of these oxidative
coupling reactions some control experiments were carried out
(Scheme 4). First,
5 equiv of radical scavenger 2,2,6,6-
tetramethyl-1-piperidinyloxyl (TEMPO) was added into the 1a
under standard conditions, and it was found that the reaction
was completely inhibited. Thus, it indicates a radical nature of
the mechanism (Scheme 4a). Next, 1a was treated with
aq.TBHP and CuSO4, afforded the corresponding peroxide 4a
(Scheme 4b). Further, to learn the reaction path, N-(1-(tert-
butylperoxy)allyl)benzamide 4a was treated with triazole under
the optimized conditions, the desired aminoimide 2aa was
obtained respectively, and the absence of nucleophilic amine
source, afforded the corresponding imide 3a. It gives clear idea
that the reaction goes through the tert-butylperoxy intermediate
(Scheme 4c). Also, N-acryloylbenzamide 3a when subjected to
the optimized conditions gave amino imide 2aa (89%) with
triazoles. It demonstrated that triazoles would participate via
aza-Michael addition pathway (Scheme 4d).
In conclusion we have demonstrated C-H functionalization
of N-allylbenzamide derivatives by an efficient novel copper
catalyzed protocol in “one-pot” fashion. The direct oxo-amination
of N-allylbenzamide derivatives into the β-aminoimide involved
mild conditions using TBHP as the oxidant, CuSO4 as the
catalyst, Cs2CO3 as the base, and triazole as a nucleophilic
amine source. Subsequently, the direct amidation of N-
On the basis of the control experiments and previous
reports, we propose a possible mechanism as shown in Scheme
5. Initially, the first step involves a TBHP cleavage initiated by a
copper (II) species to give a tert-butoxy radical.[10f,12] The tert-
3
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COMMUNICATION
Chem. Commun. 2014, 50, 10445. h) S. Rajamanickam, G. Majji, S. K.
Santra, B. K. Patel, Org. Lett. 2015, 17, 5586.
allylbenzamide derivatives into the N-acryloylbenzamides under
same oxidative conditions. Efforts to find newer applications of
this protocol are currently underway in our laboratory.
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Experimental Section
General procedure for the synthesis of β-amino imide 2aa
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N-Allylbenzamide 1a (0.1 g, 0.62 mmol.), TBHP (70 % in H2O, 0.12
mL, 1.24 mmol.) and CuSO4 (10 mol%, 0.01 g, 0.062 mmol.) was
dissolved in CH3CN (2 mL) room temperature. Then, Cs2CO3 (0.4 g, 1.24
mmol.) and Benzotriazole (73 mg, 0.62 mmol.) was added and the
resultant solution was stirred for 8 h at same temperature. The reaction
was monitored by TLC analysis until the starting material was consumed.
After the reaction was extracted with EtOAc, dried over anhydrous
Na2SO4, filtered, and concentrated under vacuum to get crude. The
crude was purified by silica gel column chromatography using EtOAc:
hexane as eluents to afford corresponding product 2aa.
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General procedure B for the synthesis of N-Acryloylbenzamide 3a
N-Allylbenzamide 1a (0.1 g, 0.62 mmol.), TBHP (70 % in H2O, 0.12
mL, 1.24 mmol.) and CuSO4 (10 mol%, 0.01 g, 0.062 mmol.) was
dissolved in CH3CN (2 mL) at room temperature. Then, Cs2CO3 (0.4 g,
1.24 mmol.) was added and the resultant solution was stirred for 6 h at
same temperature. The reaction was monitored by TLC analysis until the
starting material was consumed. After the reaction was extracted with
EtOAc, dried over anhydrous Na2SO4, filtered, and concentrated under
vacuum to get crude. The crude was purified by silica gel column
chromatography using EtOAc: hexane as eluents to afford corresponding
product 3a.
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Acknowledgements
[13] Y. Sato, A. Katz, E. Mosettig, J. Am. Chem. Soc. 1957, 73, 880.
J.R thanks CSIR New Delhi for research fellowship. I thank Dr.
Balasubramanian Sridhar for X-ray analysis, Laboratory of X-ray
Crystallography,
CSIR-IICT.
CSIR-IICT
Commun.
No.
IICT/pubs./2018/0269.
Keywords: copper-catalyzed • oxidative coupling • oxo-
amination • regioselectivity • imides
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4
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Entry for the Table of Contents
Difunctionalization of N-allylbenzamide with triazole as nucleophilic amine source under mild reaction
conditions (CuSO4/TBHP/Cs2CO3) provided β-aminoimides in excellent regioselectivity. Also, the direct
amidation of N-allylbenzamide derivatives into the N-acryloylbenzamides.
5
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