Highly efficient three-component Strecker-type reaction catalyzed by MgI2 etherate under solvent-free conditions

Article abstract of DOI:10.1016/j.tetlet.2017.03.087

A concise, straightforward and efficient method has been developed for the synthesis of α-aminonitriles by an one-pot three-component condensation of aldehydes or ketones, amines and trimethylsilyl cyanide catalyzed by MgI₂ etherate under solvent-free conditions. This protocol has some advantages such as mild reaction condition, simple work-up, short reaction time and high product yields.

Full text of DOI:10.1016/j.tetlet.2017.03.087

Accepted Manuscript
Highly Efficient Three-component Strecker-type Reaction Catalyzed by MgI2
Etherate Under Solvent-free Conditions
Pengcheng Li, Yongdong Zhang, Zhili Chen, Xingxian Zhang
PII:
S0040-4039(17)30418-5
DOI:
http://dx.doi.org/10.1016/j.tetlet.2017.03.087
TETL 48788
Reference:
To appear in:
Tetrahedron Letters
Received Date:
Revised Date:
Accepted Date:
9 January 2017
30 March 2017
31 March 2017
Please cite this article as: Li, P., Zhang, Y., Chen, Z., Zhang, X., Highly Efficient Three-component Strecker-type
Reaction Catalyzed by MgI Etherate Under Solvent-free Conditions, Tetrahedron Letters (2017), doi: http://
2
dx.doi.org/10.1016/j.tetlet.2017.03.087
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Graphical Abstract
Highly Efficient Three-component Strecker-
type Reaction Catalyzed by MgI Etherate
2
Under Solvent-free Conditions
Pengcheng Li , Yongdong Zhang , Zhili Chen, Xingxian Zhang
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310032, P. R. China.
CN
O
1
0 mol% MgI (Et2O)n
R3
2
R3 NH2
TMSCN
R1
R1
R2
NH
R2
solvent-free
1
R = aryl, heteroaryl, alkyl
2
R = H, alkyl
3
R = aryl, alkyl

1
Tetrahedron Letters
Highly Efficient Three-component Strecker-type Reaction Catalyzed by MgI2
Etherate Under Solvent-free Conditions
Pengcheng Li, Yongdong Zhang, Zhili Chen, Xingxian Zhang
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310032, P. R. China
ARTICLE INFO
ABSTRACT
Article history:
Received
A concise, straightforward and efficient method has been developed for the synthesis of α-
aminonitriles by a one-pot three-component condensation of aldehydes or ketones, amines and
Received in revised form
Accepted
Available online
2
trimethylsilyl cyanide catalyzed by MgI etherate under solvent-free conditions. This protocol
has some advantages such as mild reaction condition, simple work-up, short reaction time and
high product yields.
2
017 Elsevier Ltd. All rights reserved.
Keywords:
Strecker reaction
Aldehydes
Ketones
Amines
Trimethylsilyl cyanide
2
MgI etherate
Solvent-free condition
1
1
12
1
. Introduction
to imines and carbonyl double bonds by a variety of Lewis or
Bronsted acidic catalysts such as
α-Aminonitriles are significantly important intermediates for
1
3a
13b
13c
13d
13e
13f
Fe(Cp) PF ,
InI ,
RhI3,
Cu(OTf) ,
I ,
BiCl3,
the synthesis of a wide variety of amino acids, amides, diamines,
and nitrogen-containing heterocycles. Subsequent hydrolysis of
α-aminonitriles is the most straightforward route for the synthesis
of α-amino acids on both lab and technical field. Furthermore, α-
amino acids are in turn of great biological and economical
importance due to their outstanding performance in chemistry
and biology, and are potential as chiral building blocks. In recent
years, multicomponent reactions(MCRs) and a series of useful
compounds synthesized by this method have been reported.
2
6
3
2
2
1
13g
13g
13h
13i
La(NO
GaCl3,
)
6H
O,13k GdCl
6H
O,
NiCl
,
Ga(OTf)
,
3
3
2
3
2
2
3
1
3j
13l
13m
13n
13o
CeCl ,
Pr(OTf)3,
RuCl3,
FeCl3,
p-TsOH,
In addition, some
heterogeneous catalysts have been reported in current years
14b
3
1
3p
2- 13q
Fe O –BF
and Fe O @ZrO /SO .
3 4 2 4
3
4
3
1
4a
including polymer-supported scandium triflate,
K PdCl ,
2 4
14d
1
4c
2
poly(4-vinylpyridine)-SO complex,
guanidine HCl
More recently, the solid solution
metal−organic frameworks such as [In Ga (O C H ) (hfipbb)]
and
2
1
4e
MCM-41-SO H.
3
3
x
1−x
2
2
4 0.5
1
5
and [In O(btb) (HCOO)(L)] has also been introduced.
Among them, α-aminonitriles, prepared by MCRs of aldehydes
or ketones, amines, and cyanide sources, have attracted
considerable attention as synthetic targets.
3
2
Although, α-aminonitriles can be obtained by the aforementioned
strategies, it is highly desirable to develop methods that will
overcome the inherent limitations, such as harsh reaction
conditions, poor substrate generality and tedious work-up
procedures. Therefore, the development of less expensive,
environmentally benign, and easily handled promoters for the
synthesis of α-aminonitriles by Strecker condensation under
neutral, mild, and convenient condition is still highly desirable.
Among the methods reported for the synthesis of α-
4
aminonitriles, Strecker reaction is one of the most important
multicomponent reactions in organic chemistry for direct one-pot
synthesis of α-aminonitriles. In general, α-aminonitriles are
synthesized by the reactions of aldehydes or ketones with amines
in the presence of a cyanide source such as HCN, KCN,
TMSCN, Bu SnCN, Et AlCN, (EtO) P(O)CN, EtOCOCN,
MeCOCN, K [Fe(CN) ] and acetone cyanohydrin. Among
these cyanide sources, trimethylsilyl cyanide(TMSCN) is a
promising candidate, due to its character as easily-handled
operation and high solubility in organic solvents and relatively
safe cyanation reagent. It is noteworthy that TMSCN has been
promoted with its remarkable behavior of nucleophilic addition
5
6
7
8
9a
9b
9c
9d
Magnesium(II) species are widely applied as Lewis acid
catalysts in various functional transformations and C-C bond-
forming reactions due to the high electrophilicity of the Mg ion
3
2
2
9
e
9f
10
2
6
2
+
and its tendency to form a multi-coordinate (up to 5 or 6)
1
6
17
complex. In our previous papers, we have demonstrated that
MgI etherate could efficiently catalyze the Mukaiyama aldol
reaction of aldehydes with trimethylsilyl enolates, Clauson-Kass
reaction and Paal-Knorr condensation. In continuation of our
2
—
——
*
Corresponding authors. Tel.: +86 571 88320320; fax: +86 571 88320913; e-mail address: zhangxx@zjut.edu.cn.
1

2
Tetrahedron Letters
ongoing research field, we wish to report a mild, efficient, and Table 1. The Strecker-type reaction of aldehydes, amines with TMSCN
highly chemoselective one-pot three-component Strecker
reaction of various aldehydes or ketones, amine with TMSCN
a
2
catalyzed by MgI etherate under solvent-free condition.
catalyzed by MgI etherate under solvent-free conditions.
2
Time
h)
b
Entry
Aldehyde
Amine
Product
Yield (%)
(
1
2
3
4
1a
0.5
0.5
0.6
0.3
95
1b
1c
1d
97
91
98
Scheme 1. MgI
aldehydes or ketones, amines and trimethylsilyl cyanide.
2
etherate-catalyzed three-component Strecker reaction of
2
. Results and discussion
5
6
7
1e
1f
2.0
1.0
0.5
82
86
98
The three-component Strecker-type reactions were
successfully carried out based on a series of various aldehydes,
amines and TMSCN by using one-pot protocol in the presence of
catalytic amount of MgI etherate (10 mol %) under solvent-free
2
1g
conditions and gave good to excellent yields. The results were
summarized in Table 1.
O2N
CHO
8
9
1h
1i
0.5
1
98
90
Under the screening of substrates for different substituents in
benzaldehyde and aniline, the results revealed following delicate
electronic effects: (1) aromatic aldehydes bearing an electron-
donating group (i.e. OMe, Me) deactivated aromatic aldehydes
and afforded the corresponding α-aminonitriles in moderate to
good yields (Table 1 entries 5 and 6); (2) aromatic aldehydes
1
0
1j
1
1
1
1
1
1
88
86
87
85
90
88
11
12
13
1k
bearing an electron-withdrawing group (i.e. Br, NO ) tend to
2
react much faster and provided the corresponding products in
nearly quantitative yields (Table 1, entries 7 and 8); (3) anilines
bearing an electron-donating group (i.e. OMe, Me) reacted faster
than anilines and afforded the corresponding α-aminonitriles in
excellent yields (Table 1, entries 2-4). Among them, 4-
methylaniline exhibited relatively high reactivity than 2-
methylaniline perhaps due to the steric hindrance of 2-
methylaniline (Table 1 entries 2 and 3). In addition, 1-
naphthaldehyde, which contains a highly-conjugated plane,
seems to be quite effective, and gave the corresponding product
1l
1m
1n
1o
1
1
4
5
CHO
1
6
1p
1q
1
92
95
CHO
in 90% yield (Table 1, entry 9). Especially, MgI etherate worked
2
well with acid sensitive electron-rich heterocyclic aldehydes such
as furfural, thiophene-2-carbaldehyde, which provided the
corresponding products in high yields (Table 1, entries 10-13).
Furthermore, we have examined the Strecker-type reaction of
aliphatic aldehydes with 4-methoxylaniline (Table 1, entries 14
and 15). As well, the corresponding products were obtained with
good yields. Gratifyingly, the similar reactivity of pivalaldehyde
with higher steric hindrance was observed under the same
conditions. In addition, we investigated the three-component
Strecker–type reaction of aromatic or heteroaromatic aldehydes,
benzylamine and TMSCN in the presence of 10 mol% of MgI2
etherate under solvent-free conditions. All aldehydes
demonstrated considerable activity and provided the inspiring
results in short reaction time with good to excellent yields (Table
17
0.4
1
1
2
8
9
0
1r
1s
0.5
1
95
84
1t
1u
1v
0.4
0.5
0.5
94
92
90
21
2
2
1
,
entries 16-20). The highly sterically hindered 1-
8
6
adamantylcarboxaldehyde could also afford α-aminonitrile in
good yield. Moreover, α, β-unsaturated aldehydes such as
cinnamaldehyde gave good yield of 1,2-addition product in a
short time without formation of any polymerization products
23
1w
0.6
(dr = 72 :
c
28)
a
The reaction was carried out by addition of aldehyde (5 mmol), amine (5
mmol) with TMSCN (6 mmol) catalyzed by 10 mol % MgI under
2
2 n
(OEt )
solvent-free condition at room temperature.
(
(
Table 1, entries 21 and 22). The reaction between benzaldehyde,
S)-α-phenylethylamine and TMSCN was successfully carried
b
c
Isolated yield by silica gel flash chromatography.
1
Ratio of diastereoisomers was determined by H NMR analysis.
out catalyzed by MgI etherate and afforded the corresponding α-
2
aminonitrile in good yield with moderate enantioselectivity
(
Table 1, entry 23).
In order to expand the scope of substrates and explore further
catalytic activity of MgI etherate, a variety of aromatic and
2

3
aliphatic ketones were examined in the presence of 10 mol% of
It showed that aromatic ketones bearing an electron-
MgI etherate at 70 C under solvent-free conditions. (Table 2)
withdrawing group afforded the products in a short time with
excellent yields (Table 2, entry 5). These results above could be
proved by the experiment of 2,2,2-trifluoroacetophenone and
aniline (Table 2, entry 6). On the other hand, aromatic ketones
bearing an electron-donating group required prolonged reaction
time and provided the desired α-aminonitriles in moderate yields
(Table 2, entries 7-9). In Strecker-type reaction between aniline
or benzylamine and propiophenone, we have found that aniline
and benzylamine both have parallel reactivity to propiophenone
and afforded α-aminonitriles in excellent yields, respectively.
(Table 2, entries 10, 11). The experiment of 2-acetylthiophene,
aniline and TMSCN has also been successfully carried out in
2
Although ketones show lower reactivity in comparison to
aldehydes due to more steric hindrance around their carbonyl
group, MgI2 etherate worked well with various examined
ketones. As shown in Table 2, the Strecker reaction of
acetophenone with different substituted aniline or secondary
amine (such as morpholine) afforded the corresponding α-
aminonitriles with excellent yields (Table 2, entries 1-4). It
showed that aromatic ketones bearing an electron-withdrawing
group afforded the products in a short time with excellent yields
(
Table 2, entry 5).
Table 2. The Strecker-type reaction of ketones, amines with TMSCN
9
0% yield (Table 2, entry 12). To determine the functional group
a
2
catalyzed by MgI etherate under solvent-free condition.
tolerance and to establish the generality of this method, we have
studied Strecker reaction with typical aliphatic ketones under
regular conditions, the expected α-aminonitriles were also
obtained in the presence of catalytic amount of MgI etherate in
2
excellent yields under solvent-free conditions (Table 2, entries 13
and 14).
b
Entry
1
Ketone
Amine
Product
Time (h)
1.0
Yield (%)
A proposed mechanism for the synthesis of α-aminonitriles by
three-component reaction of aldehydes or ketones, amines and
2a
95
TMSCN catalyzed by MgI etherate is shown in Scheme 2. It is
2
assumed that aldehydes or ketones may form oxonium salt I with
2
3
4
2b
2c
2d
1.0
1.0
1.0
93
96
94
MgI etherate from its high oxophilic character, followed by
2
nucleophilic addition of amine to form an activated imine II
accompanied by an elimination of water. The cationic character
of this more Lewis acidic Mg(II) coordination with peripheral
ethereal ligands results from the dissociation of iodide ion in
accordance with the coordination of the Lewis basic imine group.
Thus, the activated imine II undergoes nucleophilic addition by
TMSCN to afford the corresponding α-aminonitriles and led to
NH2
H3C
O
CH3
5
6
2e
2f
0.5
0.5
96
97
regeneration of MgI etherate. In this process, the catalyst MgI
2
2
etherate plays a vital role in the activation of the carbonyl group
to form the imine and in the activation of the imine to react with
TMSCN.
R2
O
R1
O
CH3
7
8
9
2g
2h
2i
4.0
4.0
5.0
86
88
86
H3C
R3
MgI .(OEt )
2
2 n
O
HN
R2
+
.
CH3
CH3
R1
MgI (OEt2)n
I-
CN
R2
R1
O
H3C
I
R3 NH2
O
MgI .(OEt2)n
R3
R1
N
+
TMSI
H O
2
H3CO
CN
R2
R2
+
I-
III
MgI
.(OEt2)n
1
1
0
1
2j
1.0
1.0
92
95
R1
N
R3
II
TMSCN
2k
Scheme 2. Proposed mechanism of Strecker-type reaction of aldehydes or
O
ketones, amines with TMSCN catalyzed by MgI etherate
2
S
1
1
2
3
2l
2.0
1.0
90
95
CH3
In conclusion, we have developed an efficient, inexpensive
method for the synthesis of α-aminonitriles using solvent-free
2m
Strecker reaction catalyzed by MgI etherate. In this context,
2
MgI etherate as a mild Lewis acid demonstrates a remarkable
catalytic performance due to its high electrophilic character to
2
14
2n
1.0
92
a
oxygen atom and nitrogen atom. In the catalysis of MgI etherate
2
The reaction was carried out by addition of aldehyde (5 mmol), amine (5
mmol) with TMSCN(6 mmol) catalyzed by 10 mol % MgI (OEt under
under solvent-free conditions, a class of structurally diverse α-
aminonitriles have been obtained. Application of this catalyst not
only provide substantial improvements in the reaction rates and
yields, but also avoids the use of hazardous catalysts or solvents.
2
2 n
)
solvent-free condition at 70 C.
b
Isolated yield by silica gel flash chromatography.
3

4
Tetrahedron Letters
1
4. (a) Das, B.; Ramu, R.; Ravikanth, B.; and Reddy, K. R. Synthesis, 2006,
419; (b) Karmakar, B. and Banerji, J. Tetrahedron Lett. 2010, 51, 2748;
c) G. A. Olah, T. Mathew, C. Panja, K. Smith and G. S. Prakash, Catal.
Moreover, simple work-up procedure, environmental friendliness
and mild condition will make this present approach a promising
methodology for the Strecker reaction.
1
(
Lett. 2007, 114, 1; (d) A. Heydari, A. Arefi, S. Khaksar and R. K.
Shiroodi, J. Mol. Catal. A: Chem. 2007, 271, 142; (e) M. G. Dekamin
and Z. Mokhtari, Tetrahedron, 2012, 68, 922;
Acknowledgments
1
5. ꢀaꢁ Aguirre-ꢂꢃaꢄ, ꢅ. M.ꢆ ꢇꢈndara, F.ꢆ Iglesias, M.ꢆ ꢉneꢊꢋo, ꢌ.ꢆ ꢇutiꢍrreꢄ-
ꢎuebla, ꢏ. and Monge, M. ꢐ. J. Am. Chem. Soc. 2015, 137, ꢑ1ꢒꢓ. ꢀbꢁ
ꢔeinares-Fisac, ꢂ.ꢆ Aguirre-ꢂꢃaꢄ, ꢅ. M.ꢆ Iglesias, M.ꢆ ꢉneꢊꢋo, ꢌ.ꢆ
ꢇutiꢍrreꢄ-ꢎuebla, ꢏ.ꢆ Monge, M. ꢐ. and ꢇꢈndara, F. J. Am. Chem. Soc.
We acknowledge the financial support from National Natural
Science Foundation of China. (21372203, 21272076)
2
016, 138, 9089−909ꢓ.
16. For review see: Zhang, X. X.; Li, W. D. Chin. J. Org. Chem., 2003, 23,
185.
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Chem., 2015, 39, 4821.

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Research Highlights:
►
MgI etherate could catalyze one-pot three-component Strecker-type condensation. ►This magnesium-
2
catalyzed Strecker-type addition is rapid, mild and convenient.
►
►
The unique reactivity of this catalytic system was demonstrated.
The condensation of various aldehydes or ketones is performed in excellent yields.
1
8.
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