An organocatalytic C-C bond cleavage approach: A metal-free and peroxide-free facile method for the synthesis of amide derivatives

Article abstract of DOI:10.1039/d0nj04158k

A facile organocatalytic approach has been devised towards the synthesis of amide derivatives using 1,3-dicarbonyls as easily available acyl-sources under peroxide-free reaction conditions. This transformation was accomplished by the cleavage of the C-C bond in the presence of TEMPO as an organocatalyst and excludes the use of transition-metals and harsh reaction conditions. A broad range of substrates with diverse functional groups were well tolerated and delivered the products in high yields.

Full text of DOI:10.1039/d0nj04158k

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DOI: 10.1039/D0NJ04158K
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Organocatalytic C-C Bond Cleavage Approach: A Metal-Free and
Peroxide-Free Facile Method for the Synthesis of Amide
Derivatives
Received 00th January 20xx,
Accepted 00th January 20xx
a
a
b
c
Nagaraju Vodnala, Raghuram Gujjarappa, Saibabu Polina, Vanaparthi Satheesh, Dhananjaya
a
a
a
DOI: 10.1039/x0xx00000x
Kaldhi, Arup K. Kabi and Chandi C. Malakar*
A facile organocatalytic approach has been devised towards the bond cleavage strategy using acetone as simple acylating agent
6f
synthesis of amide derivatives by using 1,3-dicarbonyls as easy in the presence of Cu(II)-complex as catalyst. Here, we have
available acyl-sources under peroxide-free reaction conditions. This described a method that relies on the cleavage of C-C bonds of
transformation was accomplished by cleavage of C-C bond in the linear molecules using TEMPO as organocatalyst to deliver
11
presence of TEMPO as organocatalyst, which excludes the use of amide derivatives as final product.
transition-metals and harsh reaction conditions. A broad range of
substrates with diversity of functional groups were well tolerated
and delivered the products in high yields.
Scheme 1. Approaches for N-acylation of amines using C-C
bond cleavage
Introduction
During the recent years, selective C-C bond cleavage remains as
one of the significant topics of novel research area in organic
1
synthesis due to the high C-C bond strength. In this field, a
number of expensive transition metals have been investigated
as catalysts.2 Including the use of transition metals, most of
the research rely on the concept of relief of ring strain,
attainment of aromaticity and intramolecular addition in which
-4
2
-
the C-C bond is forced into close proximity to the metal center.
4
The concept of C-C bond cleavage has reached thoughtful
attention due to their broad synthetic utilities towards
biologically active compounds and stands as viable alternative
5
-10
rather than traditional methods in synthetic chemistry.
For
this purpose, transition metals like Fe(III), Cu(I), Cu(II) were
5
-6
examined thoroughly (Scheme 1). However, the development
of metal-free approaches towards C-C bond cleavage remains
7
-10
rarely explored (Scheme 1). After having extensive literature With the objective of developing an organocatalytic approach
survey, it has been found that Wang et al. developed C-C bond towards the synthesis of amide derivatives, we have performed
8
cleavage of 1,3-diketones using harsh oxidising agent.
the reaction using aniline (1a) and acetylacetone (2a) as model
Adimurthy et al. reported the AIBN promoted C-C bond substrates (Table 1). Initially, the reaction between aniline (1a)
cleavage of 1,3-diketones towards the synthesis of amide and acetylacetone (2a) was carried out in presence of 20 mol%
9
t
derivatives. Our research group have previously reported C-C NaO Bu in DMSO at 120 °C for 24 hours, which lead to the
unsuccessful results and the formation of the product was not
observed (Table 1, Entry 1). The reaction conditions were
a. Department of Chemistry, National Institute of Technology Manipur, Imphal -
95004, Manipur, India. E-mail: cmalakar@nitmanipur.ac.in.
Department of Chemistry, CHRIST (Deemed to be University), Bangalore - 560029,
India.
Schulich Faculty of Chemistry, Technion-Israel Institute of Technology, Haifa -
inefficient towards the formation of the product, even when the
7
t
b.
transformation was carried out using 1 equiv. of NaO Bu (Table
1, Entry 2). Interestingly, it was found that if the reaction is
c.
performed using a combination of 10 mol% of TEMPO (2,2,6,6-
3
200003, Israel.
t
Electronic Supplementary Information (ESI) available: [details of any supplementary tetramethylpiperidin-1-yl)oxyl) and 1 equiv. of NaO Bu, the
information available should be included here]. See DOI: 10.1039/x0xx00000x
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formation of the product 3a can be realized in 53% isolated yield observed that in absence of catalyst and base theVireewaAcrtticiolenOndlinide
(
Table 1, Entry 3). Next, to examine the efficiency of these not proceed towards the formation of desDiOreI:d10p.r1o03d9u/cDt0(NTJa0b4l1e581K,
reaction conditions several bases were screened for this Entries 19-20). Having attempted the substantial optimization
process, the maximum yield of product 3a was obtained when
the reaction of aniline (1a) and acetylacetone (2a) was carried
out in presence of 10 mol% TEMPO as catalyst and 2.0 equiv.
NaO Bu as base in toluene at 100 °C for 16 hours (Entry 15).
Table 1. Optimization of reaction conditions a
t
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Scheme 2. Substrate scope for the organocatalytic N-
acylation of amines 1b-w with acetylacetone (2a)
Entry
Catalyst (mol%)/
Base (equiv.)
Reaction
conditions
Yield
% 3a
0
0
53
29
31
27
0
b
t
1
2
3
4
5
6
7
8
9
-/NaO Bu (0.1)
-/NaO Bu (1)
TEMPO (10)/NaO Bu (1)
TEMPO (10)/KO Bu (1)
TEMPO (10)/LiO Bu (1)
TEMPO (10)/LiHMDS (1)
TEMPO (10)/NaOH (1)
TEMPO (10)/Cs
TEMPO (10)/K
DMSO, 120, 24
DMSO, 120, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO, 100, 16
DMSO,100, 16
t
t
t
t
2
CO
PO
3
(1)
(1)
0
0
47
3
4
t
1
0
TEMPO (10)/NaO Bu
1.5)
(
t
1
1
1
1
1
1
1
2
3
4
5
6
TEMPO (10)/NaO Bu (2)
TEMPO (10)/NaO Bu (2)
TEMPO (10)/NaO Bu (2)
TEMPO (10)/NaO Bu (2) Dioxane, 100, 16
TEMPO (10)/NaO Bu (2) Toluene, 100, 16
TEMPO (10)/NaO Bu (2)
DMSO, 100, 16
DMF, 100, 16
THF, 100, 16
69
54
43
39
85
27
61
47
0
t
t
t
t
t
Toluene, 50, 16
t
17
18
TEMPO (10)/NaO Bu (2) Toluene, 100, 10
TEMPO (5)/NaO Bu (2)
t
Toluene, 100, 16
Toluene, 100, 16
Toluene, 100, 16
t
1
2
9
0
-/NaO Bu (2)
TEMPO (10)/-
0
a
Unless otherwise indicated: All reactions were performed
using 1 mmol aniline (1a), 1.2 mmol acetylacetone (2a), 0.1
t
mmol TEMPO, 2 mmol NaO Bu in 2 mL of solvent under air.
b
Isolated yields.
reaction (Table 1, Entries 4-9). It was noticed that the bases like
t
t
KO Bu, LiO Bu and LiHMDS were moderately active (Table 1,
Entries 4-6). However, NaOH, Cs CO and K PO as bases were
completely inefficient to accomplish this transformation (Table
, Entries 7-9). To test the amounts of base required for this
2
3
3
4
1
reaction, we have carried out the experiments using 1.5 equiv.
and 2.0 equiv. of NaO Bu and it was investigated that in
presence of 2 equiv. NaO Bu, the transformation was
accomplished with 69% isolated yield of the product 3a (Table
t
t
1
, Entries 10-11). Next, the requirement of suitable solvent was
examined for this transformation (Table 1, Entries 12-15).
Among the tested solvents, toluene as solvent showed the
highest efficiency with formation of corresponding product 3a
in 85% isolated yield (Entry 15) and other solvents revealed
unsatisfactory results with low yields of the corresponding
product (Entries 12-14). Moreover, variation of the
temperature, time and amounts of catalyst deliver the
inadequate results (Table 1, Entries 16-18). Finally, it was also
After successfully developing the organocatalytic reaction
conditions, we have screened a broad spectrum of anilines 1
containing both electron donating and electron withdrawing
groups towards the efficient formation of various amide
derivatives 3. It was inferred that both mono-substituted and
i
di-substituted anilines 1b-o with electron donating (-Me, - Pr, -
OMe) and electron withdrawing (-F, -Cl, -Br, -I, -CF ) groups
3
2
| J. Name., 2012, 00, 1-3
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were tolerated well to afford the corresponding amides 3 in
high yields irrespective of the substitution pattern on the
aromatic ring. Nevertheless, moderate yields of the amide
products 3p-r were observed when the reaction was carried out
using nitro aniline derivatives 1p-r. In continuation, we were
curious to know about the reactivity of commercially available
drug such as sulfanilamide under the developed N-acetylation
reaction. Surprisingly, the reaction conditions gave the
corresponding N-acetylated sulfanilamide 3s in 56% yield. We
have also established the reaction of 2-aminophenol (1t)
towards the selective N-acetylation in 78% yield. At last, we
tried to extend the applicability of the reaction conditions to
sencondary amines and to serve this purpose, we have carried
out the reactions of N-methylaniline (1u), pyrrolidine (1v) and
Scheme 4. Control experiments to establisVhiewrAertaiccletOionnline
DOI: 10.1039/D0NJ04158K
mechanism
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-piperidinone (1w) to obtain corresponding N-acetylated
products 3u-w in 53-63% yields (Scheme 2).
On the other hand, various acyl-sources 2b-j have been tested
under the optimized conditions. It was found that 1,3-diketones
2
b-e are slightly more efficient than the corresponding β-
ketoesters 2h-j towards the preparation of amide derivative 3a
in good yield. However, the 1,3-diketones 2f-g did not react
under the developed reaction conditions to give the
corresponding amide derivative 3a. The rationale behind the
unreactivity of 1,3-diketones could be the bulkiness of the
group present adjacent to carbonyl group in case of 1,3-
diketones 2f-g (Scheme 3).
Scheme 3. Substrate scope for N-acylation with various 1,3-
dicarbonyls
The reaction conditions responded with an unsatisfactory yield
2
atmosphere and an enhanced yield of 3a
in 88% under O atmosphere. The above attained result
of 3a in 21% under N
2
enhances the necessity of oxygen atmosphere on the desired
product formation. Next, we perfomed the reaction of 1a and
2a under the influence of radical scavenger (BHT) to validate the
radical pathway. To our surprise, the reaction conditions
resulted in lower yields of product 3a upon using different
equiv. of BHT (butylated hydroxytoluene) (Scheme 4, Eq. 3 and
4). To evaluate the necessity of TEMPO as organocatalyst, we
have carried out the reaction of 1a and 2a in absence of TEMPO
2
under the influence of O atmosphere (Scheme 4, Eq. 5). The
After exploring a considerable substrate scope by employing reaction conditions reslulted in trace amount of product 3a.
the developed reaction conditions, we determined to construct Further, to corroborate the formation of H O during the
a feasible reaction mechanism for this transformation. To gain reaction interim, a reaction of 1a and 2a was perormed by using
further insight into the reaction mechanism, we have carried 2 equiv. of H O with and without TEMPO under N atmosphere
out relevant control experiments. To start with, we have (Scheme 4, Eq. 6 and 7). To our realization, the reaction
performed the reaction of aniline (1a) with acetylacetone (2a) conditions gave a conflicting yields of 76% and 42% respectively.
using standard reaction conditions under N
separately (Scheme 4, Eq. 1 and Eq. 2).
2
2
2
2
2
2 2
2 2
and O atmosphere This evidence further clarifies the uncertainity over H O
t
formation via NaO Bu-mediated aerial oxidation and need of
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 3
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TEMPO for the chemical transformation (Scheme 4, Eq. 6 and
). At last, the reaction of isolated intermediate A was carried
Conclusions
View Article Online
DOI: 10.1039/D0NJ04158K
7
In summary, we have established an efficient and operationally
convenient method for synthesizing amide derivatives using
organocatalyzed C-C bond cleavage strategy. The
transformation has been accomplished using wide range of
anilines, saturated N-heterocycles and 1,3-dicarbonyl
compounds. The C-C cleavage approaches are rarely explored
under metal-free conditions. In this sense, current
organocatalytic approach contributed effectively towards the
synthesis of variety of amides in excellent yields and good
functional group tolerance. The proposed organocatalytic
pathway was well supported by adequate control experiments
and mass-spectroscopic data.
out under standard reaction conditions to further evaluate the
mechanistic pathway. As anticipated, the reaction conditions
delivered the desired product 3a in 71% yield (Scheme 4, Eq. 8).
After a series of control experiments, we had a thought of
meticulous understanding of the mechanistic pathway. To assist
the understanding, we have carried out the reaction of aniline
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+
+
(
1a) ([M+H] = 94.1) and methyl acetoacetate (2h) ([M+2H] =
1
18.2) under standard reaction conditions. The course of the
reaction was monitored and examined by liquid
chromatography-mass spectrometry (LC–MS) after an interval
of 4 h, 8 h and 12 h. The mass-spectroscopic data revealed that
the mechanistic pathway could be prosecuted via the formation
of intermediates C ([M] = 380.0), D ([M+2H] = 230.2) to obtain
the desired product 3a ([M-H+Na] = 157.2) along with
+
+
+
Conflicts of interest
There are no conflicts to declare.
+
byproduct F ([M+H] = 89.2).
On the basis of our experimental observations and literature
evidences,8
,
12-13
a plausible mechanism has been drawn in
Scheme 5. It is expected that the intermediate B, can be formed
by the condensation reaction between substrates 1a and 2h. On
the other hand, it is also expected that, catalytic amounts of CCM appreciate Science and Engineering Research Board (SERB),
Acknowledgment
t
H O
2 2
might be generated by aerial oxidation via NaO Bu- New Delhi and Technical Education Quality Improvement Program,
1
2
mediated single electron transfer (SET) phenomenon. Next, Phase-III (TEQIP-III), Ministry of Human Resource Development
the intermediate C ([M] = 380.0), can be formed in-situ by the (MHRD), New Delhi for the financial support in the form of research
reaction between intermediate B′, TEMPO and H O . The
2 2
intermediate C experiences homolytic cleavage to deliver
+
grant (ECR/2016/000337). We sincerely thank Dodla Sivanageswara
Rao from Department of Chemistry, Malaviya National Institute of
Technology, Jaipur and Mostakim SK from Department of Chemistry,
Indian Institute of Technology, Guwahati for NMR analysis and
research support. NV, RG, DK and AKK grateful to Ministry of Human
Resource Development (MHRD), New Delhi for fellowship support.
+
product 3a ([M-H+Na] = 157.2) and radical intermediate D
+
(
[M+2H] = 230.2). The intermediate D further undergoes
oxidation with H
2
O
2
which leading to the formation of 1,2-
+
dicarbonyl compound F ([M+H] = 89.2) via intermediate E with
the regeneration of TEMPO (Scheme 5). The details of mass
spectrometric data has been provided in Figure 1 (SI).
Notes and references
1
Scheme 5. Plausible reaction mechanism for N-acylation
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DOI: 10.1039/D0NJ04158K
Rhodium(I)-Catalyzed Reactions via Carbon–Carbon Bond
Cleavage In Rhodium Catalysis in Organic Synthesis: Methods
and Reactions, (Ed.; K. Tanaka), 2019.
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New Journal of Chemistry
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DOI: 10.1039/D0NJ04158K
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Organocatalytic C-C Bond Cleavage Approach: A Metal-Free and Peroxide-Free Facile Method for the Synthesis of Amide Derivatives
Nagaraju Vodnala, Raghuram Gujjarappa, Saibabu Polina, Vanaparthi Satheesh, Dhananjaya Kaldhi, Arup K. Kabi and Chandi C. Malakar*a
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An organocatalyzed C-C bond cleavage approach has been envisioned towards the synthesis of amide derivatives from their corresponding amines and 1,3-
dicarbonyls.
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