Iron-Catalyzed Oxidative Coupling Reaction of Isocyanides and Simple Alkanes towards Amide Synthesis

Article abstract of DOI:10.1002/adsc.201801619

An iron-catalyzed oxidative coupling reaction of isocyanide and readily available alkane has been disclosed. In the presence of a catalytic amount of FeCp₂ (10 mol%), heating a mixture of alkane, isocyanide, and DTBP in DCE allows for the formation of an amide. This reaction tolerates many simple alkanes including cycloalkanes and chain alkanes. Furthermore, a series of aromatic isocyanides having different substituents on the aromatic ring are also proven to be effective reaction components. Unfortunately, the employment of aliphatic isocyanides fails to afford the desired products. The present strategy avoids tedious procedures and the employment of toxic starting materials, thus providing an environmentally benign and efficient protocol towards amide synthesis. (Figure presented.).

Full text of DOI:10.1002/adsc.201801619

Title: Iron-Catalyzed Oxidative Coupling Reaction of Isocyanides and
Simple Alkanes towards Amide Synthesis
Authors: Jian Li, Hongdong Yuan, Zhiqiang Liu, Yushu Shen, Hongbin
Zhao, Chunju Li, and Xueshun Jia
This manuscript has been accepted after peer review and appears as an
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To be cited as: Adv. Synth. Catal. 10.1002/adsc.201801619
Link to VoR: http://dx.doi.org/10.1002/adsc.201801619

10.1002/adsc.201801619
Advanced Synthesis & Catalysis
COMMUNICATION
DOI: 10.1002/adsc.201((will be filled in by the editorial staff))
Iron-Catalyzed Oxidative Coupling Reaction of Isocyanides and
Simple Alkanes towards Amide Synthesis
Hongdong Yuan,†a Zhiqiang Liu,†a Yushu Shen,c Hongbin Zhao,*a Chunju Li,a
Xueshun Jia,*a,b and Jian Li*a
a
Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University, 99 Shangda Road,
Shanghai 200444, P. R. China
Fax: (+86)-21-66132408; E-mail: hongbinzhao@shu.edu.cn; xsjia@mail.shu.edu.cn; lijian@shu.edu.cn
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.
Department of Polymer Materials, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. China
These authors contributed equally to this work.
b
c
†
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. An iron-catalyzed oxidative coupling reaction of development of other efficient and alternative
strategies.[4] Among them, the transition-metal-
isocyanide and readily available alkane has been disclosed.
In the presence of a catalytic amount of FeCp2 (10 mol%),
heating a mixture of alkane, isocyanide, and DTBP in DCE
allows for the formation of an amide. This reaction
tolerates many simple alkanes including cycloalkanes and
catalyzed hydroaminocarbonylation reaction using
carbon monoxide as carbonyl source has attracted
considerable attention due to its high atom economy.[5]
In this context, studies with Fe, Co, Ru, Ni, especially
Pd have been well documented towards amide
synthesis.[6,7] Of late, enzyme-catalyzed aminolysis of
ester or carboxylic acid offers another efficient and
direct synthesis of amide.[8] Although much progress
chain alkanes. Furthermore,
a
series of aromatic
isocyanides having different substituents on the aromatic
ring are also proven to be effective reaction components.
Unfortunately, the employment of aliphatic isocyanides
fails to afford the desired products. The present strategy
avoids tedious procedures and the employment of toxic
has
been
achieved, the
development
of
starting materials, thus providing an environmentally environmentally more benign and efficient methods
benign and efficient protocol towards amide synthesis.
for amide synthesis continues to be a significant target
of current research in organic chemistry.
Keywords: Isocyanide; Amide; Oxidative coupling;
Alkane; Iron
Amides represent one of the most important N-
containing compounds in organic chemistry since
they are present in many natural products,
pharmaceuticals, proteins, and alkaloids.[1] In addition,
they can also serve as precursors for a number of
useful transformations.[2] As such, amide synthesis
has become an important research area of interest in
current organic synthesis. Traditional methods for the
preparation of amides involve the use of activated
carboxylic acid derivatives as well as the
stoichiometric amounts of coupling reagents, which
are usually associated with tedious procedures or
harsh reaction conditions.[3] Furthermore, all these
strategies suffer from the large amount of resultant
byproducts, which brings poor atom economy and
triggers a bad environmental problem. To overcome
the above-mentioned drawbacks, many efforts from
organic community have been devoted to the
Scheme 1. Representative examples of amide synthesis
using isocyanide synthon
Isocyanides have been recognized as versatile and
valuable building blocks for a long time because of
their unique structure and reactivity.[9,10] Owing to
their classical carbene-like reactivity, for instance,
isocyanides-based multicomponent reactions (IMCRs)
have been widely investigated since the discovery of
1
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10.1002/adsc.201801619
Advanced Synthesis & Catalysis
pioneering Passerini and Ugi reaction.[11,12]
Furthermore, Lewis acid-[13] and transition-metal-
catalyzed[14] isocyanide insertion reactions (single
insertion, double insertion, and multiple insertion) are
also intensively studied. In particular, isocyanides are
found to be significant radical acceptors since the
terminal carbon of isocyanide can be attacked by
radical species for subsequent reactions.[15] Among
these investigations, new methods for amide synthesis
using isocyanide as amide precursor other than the
use of toxic carbon monoxide have received
considerable attention. In 2011, Jiang and co-workers
disclosed a palladium-catalyzed amide synthesis from
isocyanides and aryl halides (Scheme 1a).[16]
Subsequently, Cai and co-workers developed another
Pd-catalyzed approach for the aminocarbonylation of
N-tosylhydrazones with isocyanides.[17] After that,
Grimaud[18a] and Zhu[18b] reported the metal-free
coupling reaction between isocyanides and diazonium
salts, respectively (Scheme 1b). On the other hand, it
is also worthy to note that metal-catalyzed oxidative
coupling reaction has emerged as a powerful tool for
the construction of new chemical bonds in the past
years.[19] In the past several years, we have spent
much time in developing new transformations
involving isocyanides.[20] Accordingly, we envisioned
that the oxidative coupling reaction of isocyanide and
readily available simple alkane under radical
conditions might provide a novel strategy for amide
synthesis (Scheme 1c). So far, much progress has
been achieved with respect to using isocyanides as an
imidoyl synthon, whereas studies on the reactivity of
an isocyano group as an amidoyl synthon in a radical
reaction are still rare.[21]
15
FeCp2
23
DMSO
DCE
DTBP
16[c]
17[d]
<10
74
FeCp2
FeCp2
DTBP
DTBP
DCE
[a]
Unless otherwise noted, all reactions were carried out
with 4-methoxyphenyl isocyanide 1a (0.5 mmol),
cyclohexane 2a (2 ml), catalyst (10 mol %), peroxide (2.0
mmol), solvent (3 mL), 80 oC, 12 hours in sealed tube.
[b] Yields of product after silica gel chromatography.
[c] In such case, reaction temperature was 60 oC.
[d] Reaction temperature was 100 oC.
To verify our hypothesis, we initially examined the
model reaction of substrates 1-isocyano-4-
methoxybenzene (1a), cyclohexane (2a), di-tert-butyl
peroxide (DTBP), and different catalysts. As shown
in Table 1, no formation of the desired product was
observed when the mixture was heated in the presence
of CuCl and TBAI (Table 1, entry 1 and entry 2). To
our delight, upon treatment of the mixture with
catalytic amount of CuBr essentially delivered
product 3a in 36% yield (Table 1, entry 3).
Encouraged by this result, several metal salts were
subsequently explored to enhance the yield of 3a
(Table 1, entries 4-8). The experiment results revealed
that the employment of FeCp2 as catalyst could
significantly increase the yield of 3a to 85% (Table 1,
entry 8). Next, other reaction parameters including
oxidant, solvent, and temperature were carefully
screened to value different effects on present
transformation. Of the oxidants examined, tert-butyl
hydroperoxide (TBHP) and benzoyl peroxide (BPO)
exhibited very poor performance, whereas dicumyl
peroxide (DCP) showed some activity but less
effective than DTBP (Table 1, entries 9-11). Several
solvents including PhCl, MeCN, and DMSO were
attempted, but only negative results were obtained
(Table 1, entries 12-15). Further experiments also
demonstrated that the reaction temperature had
significant impact on the reaction performance (Table
1, entries 16-17).
Table 1. Reaction optimization[a]
Yield
(%)[b]
Entry
Catalyst
Peroxide
DTBP
Solvent
Table 2 Scope of the reaction with respect to the
1
2
CuCl
TBAI
DCE
DCE
DCE
0
0
isocyanide substrate [a],[b]
DTBP
DTBP
DTBP
DTBP
DTBP
DTBP
DTBP
TBHP
3
CuBr
36
4
Cu(OAc)2
Fe(OAc)2
FeCl2
trace
17
DCE
DCE
DCE
DCE
DCE
DCE
DCE
DCE
PhCl
MeCN
EtOAc
5
6
0
7
FeCl3
trace
85
8
FeCp2
9
FeCp2
0
10
11
12
13
14
41
FeCp2
FeCp2
FeCp2
FeCp2
FeCp2
DCP
BPO
trace
<10
11
DTBP
DTBP
DTBP
0
2
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10.1002/adsc.201801619
Advanced Synthesis & Catalysis
[a]
Reaction condition A: isocyanide 1 (0.5 mmol),
cyclohexane 2a (2 ml), FeCp2 (10 mol %), DTBP (2.0
mmol), DCE (3 mL), 80 oC, 12 hours in sealed tube.
[b] Yields of product after silica gel chromatography.
With the optimized conditions in hand, we
sought to evaluate the scope and limitation of present
transformation (Table 2). A wide range of substrates 1
having substituents including methoxy, halide, methyl,
tert-butyl, i-propyl groups at ortho-, meta-, and para-
positions of the aromatic ring were used to react with
cyclohexane 2a. Gratifyingly, all reactions proceeded
smoothly to produce the desired compounds 3b-3k.
Reaction with isocyanide 1l bearing a naphthyl group
also worked well to afford product 3l. Unfortunately,
aliphatic isocyanides such as cyclohexyl and tert-
butyl isocyanides failed to experience present
coupling.
[a] Reaction condition A.
[b] Yields of product after silica gel chromatography.
After a broad scope of isocyanide was established,
we decided to investigate the tolerance of substituted
alkanes. As shown in Table 3, reactions of
cyclopentane 2b with a series of substituted aromatic
isocyanides were firstly performed. Additionally,
cycloalkanes such as admantane 2c and cycloheptane
2d were also found to be effective reaction
components to produce compounds 4f-4i. After that,
we became interested in exploring the feasibility of
non-cyclic alkanes under the optimized conditions.
2,3-Dimethylbutane 2e also reacted with 4-
methoxyphenyl and 2,6-dimethylphenyl isocyanides
to yield compounds 4j and 4k. Pleasingly, these
reactions showed good regioselectivity and only one
isomer was isolated. Moreover, n-pentane was also
tolerated to give the products.
Table 3 Scope of the reaction with respect to the alkane
substrate [a],[b]
To have more insight into present oxidative
coupling reaction, several preliminary mechanistic
3
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10.1002/adsc.201801619
Advanced Synthesis & Catalysis
in Scheme 3 to explain the formation of products. The
beginning of this reaction involves a metal-catalyzed
formation of alkoxyl radical A.[23] Then, this
intermediate abstracts a hydrogen from cyclohexane
2a to yield cyclohexyl radical B with the elimination
of one molecule tert-butyl alcohol as byproduct. This
in situ formed reactive radical B is then trapped by
isocyanide 1a to generate intermediate C, which is
further oxygenated to hydroperoxide compound D in
the presence of oxygen.[24] The resultant E via
homolytic O-O scission undergoes hydrogen
abstraction and isomerization to give product 3a.
In conclusion, we have described an iron-
catalyzed oxidation coupling reaction of isocyanides
and
simple
alkanes,
thus
providing
an
environmentally benign and efficient method for
amide synthesis. The present strategy has the
following advantages: (1) abundant simple alkanes
were used as readily available starting materials; (2)
inexpensive iron was used as catalyst; (3) this method
avoids the tedious procedures associated with the
activated carboxylic acid derivatives and only tert-
butyl alcohol was yielded as sideproducts, thus
meeting the requirement of green chemistry. Further
study and application of present reaction are still
underway in our laboratory.
Scheme 2 Preliminary mechanistic study and control
experiments
experiments were next conducted. In the presence of
excessive radical scavenger TEMPO (2,2,6,6-
tetramethylpiperidine-N-oxyl), the coupling reaction
of 1a and 2a was completely inhibited, therefore
indicating a free radical process (Scheme 2, eq 1).
Another control experiment carried out under a N2
atmosphere produced <10% yield of 3a, which
suggested the participation of molecular O2 in present
transformation (Scheme 2, eq 2). Remarkably, an
intermolecular competing kinetic isotope effect (KIE)
experiment with a solution of substrate 1a, 2a and
[D]-2a was performed (Scheme 2, eq 3). At this point,
a significant KIE effect was observed (kH/kD = 13.3).
This result indicated that the C(sp3)−H bond cleavage
might be one of the rate-determining steps of this
oxidative coupling. Control experiments with
tetrahydrofuran and 1,4-dioxane under the optimal
conditions were also carried out to furnish the
corresponding products 6 and 8 (Scheme 2, eq 4 and
eq 5).
Experimental Section
General Procedure for the Formation of Amide
Under air atmosphere, a sealable reaction tube with a
Teflon-coated screw cap equipped with a magnetic stir bar
was charged with isocyanide 1 (0.5 mmol), alkane 2 (2 ml),
DTBP (2.0 mmol), ferrocene (10 mol %) in DCE (3.0 mL)
at room temperature. The rubber septum was then replaced
by a Teflon-coated screw cap, and the reaction vessel
placed in an oil bath at 80 C for 12 h. After the reaction
was completed, it was cooled to room temperature and
monitored by TLC. Then the reaction mixture was
concentrated under vacuum. The residue was purified by
flash chromatography on silica gel (eluant: petroleum
ether/ethyl acetate = 30:1) to give the desired product 3 or
4.
Acknowledgements
The authors gratefully acknowledge financial support from
National Key Research and Development Program of China
(2017YFB0102900) and State Key Laboratory of Applied Organic
Chemistry, Lanzhou University. This work is also sponsored by
Natural Science Foundation of Shanghai (18ZR1413900) and
Shanghai Pujiang Program (17PJD016).
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Advanced Synthesis & Catalysis
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10.1002/adsc.201801619
Advanced Synthesis & Catalysis
COMMUNICATION
Iron-Catalyzed Oxidative Coupling Reaction of
Isocyanides and Simple Alkanes towards Amide
Synthesis
Adv. Synth. Catal. Year, Volume, Page – Page
Hongdong Yuan, Zhiqiang Liu, Yushu Shen,
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Li*
7
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