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Nucleophilic substitution of ferrocenyl alcohols catalyzed by bismuth(III) in aqueous medium at room temperature.

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Full Paper
Received: 10 June 2011
Revised: 27 October 2011
Accepted: 25 November 2011
Published online in Wiley Online Library: 13 January 2012
( DOI 10.1002/aoc.1867
Nucleophilic substitution of ferrocenyl alcohols
catalyzed by bismuth(III) in aqueous medium
at room temperature
Ran Jiang, Chun-Xiang Yuan, Xiao-Ping Xu and Shun-Jun Ji*
A nucleophilic substitution reaction of an a-ferrocenyl alcohol with various amines, indoles and thiols was successfully developed by
using a catalytic amount of Bi(NO3)3.5H2O at room temperature without the aid of phase transfer catalyst. The reactions proceeded
in aqueous media, leading to the formation of new C=C, C=N and C=S bonds bearing ferrocenyl substituent with high efficiency.
Copyright © 2012 John Wiley & Sons, Ltd.
Supporting information may be found in the online version of this article.
Keywords: Bi(NO3)3.5H2O; aqueous media; ferrocene derivatives; room temperature
Coupling reactions between reactive nucleophiles and alkyl
halides or related species are one of the most used protocols for
the construction of new chemical bonds. However, alkyl halides
are often prepared from alcohol and the aforementioned organic
transformations using alkyl halides inevitably lead to the generation of salt waste. Thus, if a nucleophilic coupling can be realized
by direct use of alcohol instead of alkyl halide as electrophile, the
reaction will undoubtedly be more efficient and economical in the
context of green chemistry, considering that alcohol is more easily
available than alkyl halide and water is the only by-product of the
reaction. In addition, reaction using alcohol as electrophile can
simplify the purification process because the use of alkyl halide
as electrophile makes the work-up more difficult in order to
remove the salt waste generated in the reaction. However, the poor
leaving ability of the hydroxy group makes the reaction employing
alcohol as electrophile extremely difficult and challenging. Great
advances have been made in the last three decades and a number
of catalytic methods have been established to efficiently promote
transformation in common organic solvents.[1]
In recent decades, the use of water as a reaction medium has
received much attention in organic synthesis because of the
many advantages from economical, environmental, and safety
viewpoints.[2] In addition, in view of the unique physical and
chemical properties of water as compared to organic solvent, it
has been found that many reactions performed in water exhibit
unique reactivity and selectivity patterns compared with the same
reactions carried out in common organic solvents.[3] More recently,
a few examples concerning the direct nucleophilic substitution of
alcohol in water have been disclosed. For example, Kobayashi
and co-workers accomplished the synthesis of ester, ether and
dithioacetal via a dodecylbenzene sulfonic acid (DBSA)-mediated
dehydration reactions in water.[4] In addition, encouraged by this
result, a direct dehydrative nucleophilic substitution of alcohol
was also successfully realized by using the same catalyst in water
at 80 C.[5] It should be noted that, in both reactions, DBSA serves
Appl. Organometal. Chem. 2012, 26, 62–66
as both reaction surfactant and Brønsted acid catalyst. As a matter
of fact, some nucleophilic substitution of alcohols can be successfully performed even in the absence of Lewis acids, Brønsted acids
or surfactants. Cozzi et al. have demonstrated that organic transformations conducted ’on water’ at 80 C also provide an efficient
method for the construction of C=C and C=S bonds.[6] Based on
related studies in this area,[7] hydrogen bond interaction was
considered to be an influential factor in promoting the protocol.
Additionally, many ferrocene derivatives, thought to be potential
functional materials, were easily synthesized using the approach.
However, limitations, such as relatively high reaction temperature,
longer reaction time and moderate yield of product, made the
process inefficient and less economical.
On the other hand, ferrocene and its derivatives have found a
broad range of applications in material science, medicine, organic
synthesis, and other areas.[8] We have been interested in the
synthesis of ferrocene derivatives for some years.[9] Recently, we
found that new C=C and C=O bonds could be easily constructed
by the direct nucleophilic substitution of ferrocenyl alcohol in the
presence of Lewis acid catalysis.[10] In continuation of our work in
this area, Bi(NO3)3.5H2O, a cheap alternative catalyst, was first
applied in this type of reaction. It was found that Bi(NO3)3.5H2O
greatly accelerated the reaction process at room temperature,
leading to C=C, C=N, and C–S bond formation with high efficiency
(Scheme 1). In addition, Bi(NO3)3.5H2O was found superior to
cerium ammonium nitrate (CAN) in terms of reactivity, although it
was insoluble in common organic solvents.[11] Here we report these
* Correspondence to: Shun-Jun Ji, Key Laboratory of Organic Synthesis of
Jiangsu Province, College of Chemistry, Chemical Engineering and Materials
Science, Soochow University, Renai Road, Suzhou Industrial Park, Suzhou,
215123, People’s Republic of China. Email:
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry,
Chemical Engineering and Materials Science, Soochow University, Suzhou
215123, People’s Republic of China
Copyright © 2012 John Wiley & Sons, Ltd.
Bi(III) catalyzed nucleophilic substitution of ferrocenyl alcohols in water
Scheme 1. Bi(III)-catalyzed C=C, C=N and C=S bond formation in water
(m, 8H, FcH), 4.91 (q, J = 6.9 Hz, 2H, 2CH), 6.96 (dd, J = 4.8, 4.8 Hz,
2H, 5, 5′-ArH), 8.53 (d, J = 4.8 Hz, 4H, 4, 4′, 6, 6′-ArH). 13 C NMR
(75 MHz, CDCl3) d (ppm): 173.1 (Ar-C1), 157.7 (Ar-C2,4), 116.8
(Ar-C3), 90.9 (Fc-C1), 90.8 (Fc-C1′), 69.6 (Fc-C2), 69.5 (Fc-C2′), 69.4
(Fc-C5), 69.4 (Fc-C5′), 69.1 (Fc-C3), 68.9 (Fc-C3′), 67.9 (Fc-C4), 67.8
(Fc-C4′), 40.0 (CH), 22.1 (CH3), 22.1 (CH3). HRMS (EI): m/z calcd for
C22H22FeN4S2: 462.0635; found: 462.0635.
Results and Discussion
Ferrocenyl alcohols were prepared by a similar method to that
reported in the literature.[12] Other chemicals were commercially
available. Melting points were recorded on an Electrothermal
digital melting point apparatus and are uncorrected. IR spectra
were recorded on a Varian FT-1000 spectrophotometer using KBr
optics. 1H NMR (13 C NMR) spectra were recorded on a Varian INOVA
300 (75) or 400 (100) MHz spectrometer using CDCl3 or DMSO-d6
as solvent and tetramethylsilane (TMS) as internal standard. Highresolution mass spectra were obtained using a Microma GCT-TOF
instrument. All synthetic procedures with characterization data
and spectra are given in the online supporting information.
Typical Procedure for the Reaction of Ferrocenyl Alcohol
with Nuclephile
To a mixture of ferrocenyl ethanol (0.116 g, 0.5 mmol), nucleophile
(0.5 mmol, unless otherwise stated), and Bi(NO3)3.5H2O (0.0112 g,
0.025 mmol) was added H2O (1.5 mL). The reaction mixture was
stirred vigorously at room temperature until the starting materials
were completely consumed, as indicated by thin-layer chromatographic analysis. After reaction, the reaction mixture was extracted
by ethyl acetate, and the organic phase was dried with anhydrous
Na2SO4. After filtration, the solvent was removed under reduced
pressure. The residue obtained was purified by flash column
chromatography with ethyl acetate and petroleum ether as eluents
to afford pure product.
N-(1-Ferrocenylethyl)-2-chloroaniline (2aa)
123.7 mg, 73%; orange solid; m.p. 97–99 C; IR (KBr): 3396, 3094,
2968, 1595, 1500, 1031, 742 cm 1; anal. calcd for [C18H18ClFeN]
(Fw = 339.6 g mol 1), C, 63.65; H, 5.34; N, 4.12; found, C, 63.59; H,
5.30; N, 4.14%; 1H NMR (400 MHz, DMSO-d6) d (ppm): 1.45
(d, J = 6.4 Hz, 3H, CH3), 4.18–4.25 (m, 9H, FcH), 4.38–4.44 (m, 1H, CH),
4.85 (d, J = 8.4 Hz, 1H, NH), 6.62 (dd, J = 7.6, 7.6 Hz, 1H, 4-ArH), 6.89
(d, J = 8.0 Hz, 1H, 6-ArH), 7.17 (dd, J = 7.6, 8.0 Hz, 1H, 5-ArH), 7.31
(d, J = 7.6 Hz, 1H, 3-ArH). 13 C NMR (100 MHz, CDCl3) d (ppm): 143.7
(Ar-C1), 129.8 (Ar-C3), 128.3 (Ar-C5), 119.4 (Ar-C4), 117.2 (Ar-C2), 112.0
(Ar-C6), 93.7 (Fc-C1), 68.9 (Fc-C2), 68.3 (Fc-C5), 68.2 (Fc-C3), 67.3
(Fc-C4), 66.6(Fc-C′), 46.6 (CH), 20.9 (CH3). HRMS (EI): m/z calcd for
C18H18ClFeN: 339.0477; found: 339.0476.
1,1′-Bis(1-(pyrimidin-2-ylthio)ethyl)ferrocene (4ca)
Appl. Organometal. Chem. 2012, 26, 62–66
Copyright © 2012 John Wiley & Sons, Ltd.
205.6 mg, 89%; orange solid; m.p. 115–116 C; IR (KBr): 3095,
2979, 1564, 1544, 1380, 1186, 773 cm 1; anal. calcd for
[C22H22FeN4S2] (Fw = 462.4 g mol 1), C, 57.14; H, 4.80; N, 12.12; S,
13.87; found, C, 57.11; H, 4.84; N, 12.14; S, 13.84%. 1H NMR
(300 MHz, CDCl3) d (ppm): 1.81(d, J = 6.9 Hz, 6H, 2CH3), 4.26–4.35
N-Alkylation is an important method for synthesizing secondary
or tertiary amine derivatives. By using alcohols as substrates, a
variety of catalytic methods have been established for N-alkylation
or N,N-dialkylation.[5,13] However, few reactions in water have
emerged except for two examples provided by Kobayashi et al.
using DBSA as catalyst.[5] In addition, our attempt to carry out
the reactions of ferrocenyl alcohols with amine/amide on water
at 80 C failed using Cozzi’s protocol.[6b] Gratifyingly, we found
that N-alkylation using ferrocenyl alcohols as substrate could proceed smoothly in water in the presence of 5 mol% Bi(NO3)3.5H2O
at room temperature.
Initial study was performed by utilizing ferrocenyl ethanol (1a)
as model substrate. A blank test was first carried out to detect the
influence of hydrogen bond interaction upon the reaction. To our
surprise, no reaction was observed between 1a and 4-chloroaniline
(2c), even when the mixture was stirred vigorously at room temperature for 2 days. However, when 5 mol% Bi(NO3)3.5H2O was added
to the reaction mixture, rapid formation of product (2 ac) was
detected. The reaction could go to completion within 1 h, giving
rise to the desired product 2 ac in 94% yield (Table 1, entry 3).
Throughout the process, both substrate and reagent enmeshed
in water, and at the end of the reaction, after deposition of product,
an apparent blue solution that implied the presence of ferrocenium
was observed (see supporting information, Fig. S1a–d). At this
stage, we supposed that the present reaction using Bi(III) compound proceeded through a Lewis acid-catalyzed manner rather
than the effect arising from hydrogen bond activation. Compared
with other examples ’on water’,[6,14] our case can be defined as
’in water’. (Cozzi et al. suggested that the same reaction performed
in the absence of any Brønsted or Lewis acid should be defined as
’on water’ because the ferrocenyl alcohols were insoluble in water
under the conditions applied. In our case, the reactions were
carried out at room temperature in aqueous solution of bismuth
nitrate, and the ferrocenyl alcohols might exist in the form of very
small particles by vigorously stirring. The resulting blue solution
observed in some cases suggested the presence of ferrocenium
in water (Fig. S2, supporting information); therefore we considered
the reactions as ’in water’.) Next, the steric effect on the reaction
was explored as well. When the chlorine atom shifted from the
4-position to 3-position, a slightly slower reaction rate was
observed, thus resulting in decreased product yield (Table 1,
entry 2). When o-chloroaniline was introduced as substrate, a
decrease in the reaction rate as well as product yield were
detectable (Table 1, entry 1). At the same time, 4-bromoaniline, aniline, 4-nitroaniline and 4-methylaniline were employed to examine
the electronic effect. With increasing electron-releasing ability of
group at the 4- position, an obvious decrease in product yield was
seen accordingly (Table 1, entries 3–7). In the case of 4-methylaniline,
no reaction took place at all. Heteroaromatic amines, such as
8-aminquionline, can also react with 1a to afford the product in
83% yield (Table 1, entry 8). Nevertheless, as for amines bearing a
R. Jiang et al.
Table 1. Reactions of aryl amines with 1-ferrocenyl ethanola
Time (h)
Yield (%)b
2 ac
Reaction conditions: 1a (0.50 mmol), 2 (0.50 mmol), catalyst (5 mol%),
H2O (1.5 mL), at room temperature.
Yield of isolated product after flash chromatography.
similar structure, like 2-aminopyridine, no reaction occurred under
optimized conditions (Table 1, entry 9). It is worth noting that when
2 equiv. of 1a was subjected to reaction with 2c, an 85% yield of N,
N-dialkylated product was obtained after 24 h (Scheme 2). The
method provided a suitable model for the controlled synthesis of
secondary and tertiary amines.
Subsequently, indole, as a good candidate for a C-centered
nucleophile, was selected to explore the C=C bond formation in
water. The details are shown in Table 2. From the results, we
can see that mono-substituted indoles containing a methyl
group at any position, such as N1, C4, C5, C6 or C7, can react well
with ferrocenyl ethanol in water, giving the desired products in
good to excellent yields within a short reaction time (entries
3–4, 6–8). With regard to 5-bromoindole, a similar yield was
furnished with a faster reaction rate (entry 5). All these protocols
displayed advantages over those performed in pure water without any catalysts.[6] However, to our surprise, 2-phenylindole, which
exhibited high activity in this type of transformation in organic
solvent, turned out to be inert in the present case even after 24 h.
We surmised that the strong hydrophobic ability of the phenyl ring
close to the nucleophilic center was of some importance.
Based on the above results, we continued to explore C=S bond
formation under the same conditions. It was found that several
arylheterocycles containing a thio group could also participate in
reaction with ferrocenyl ethanol (Table 3), and the desired products
could be isolated in moderate to high yield.
From the observation presented above, we are aware that
bismuth nitrate can accelerate the direct nucleophilic substitution of various nucleophiles to ferrocenyl ethanol in water;
thus a substrate scope survey was subsequently carried out.
As listed in Table 4, ferrocenyl methanol (1b) can react with
C-, N-, and S-centered nucleophiles to produce the desired
products in good yield (up to 91%). When ferrocenyl diol (1c)
was introduced, an intramolecular etherification between two
hydroxyl groups inevitably occurred, resulting in a relative
complexity of reaction. The product yield was satisfactory,
however, as implied in entries 4–6.
In summary, we have developed an efficient approach to constructing C=N, C=C, and C=S bond catalyzed by Bi(NO3)3.5H2O.
The reaction could be directly performed in aqueous medium
without the addition of any phase transfer catalyst, which is
consistent with the principles of green chemistry. In addition,
various ferrocenyl derivatives could be obtained in moderate to
good yield by means of this method at room temperature. Further
studies to explore the utility of this system in organic synthesis are
currently in progress in our laboratory.
Supporting information may be found in the online version of
this article.
Scheme 2. Bi(III)-catalyzed N,N-dialkylation of arylamine
Copyright © 2012 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2012, 26, 62–66
Bi(III) catalyzed nucleophilic substitution of ferrocenyl alcohols in water
Table 2. Reactions of indoles with 1-ferrocenyl ethanola
Time (h)
Yield (%)b
3 ac
Reaction conditions: 1a (0.50 mmol), 3 (0.50 mmol), catalyst (5 mol%), H2O (1.5 mL), at room temperature.
Yield of isolated product after flash chromatography.
Table 4. Reactions of other 1-ferrocenyl alcohol and nucleophilea
Time (h)
Yield (%)b
2 cc
Table 3. Reactions of C=S bond formation catalyzed by Bi(III).a
Time (h)
Yield (%)b
Appl. Organometal. Chem. 2012, 26, 62–66
Reaction conditions: 1a (0.50 mmol), 3 (0.50 mmol), catalyst (5 mol%),
H2O (1.5 mL),at room temperature.
Yield of isolated product after flash chromatography.
1.0 mmol nucleophile was added.
Copyright © 2012 John Wiley & Sons, Ltd.
Reaction conditions: 1a (0.50 mmol), 4 (0.50 mmol), catalyst (5 mol%),
H2O (1.5 mL), at room temperature.
Yield of isolated product after flash chromatography.
R. Jiang et al.
This work was partly supported by the National Natural Science
Foundation of China (No. 21042007, 21172162), Natural Science
Basic Research of Jiangsu Province for Higher Education (No.
10KJB150016), a research grant from the Innovation Project for
Graduate Student of Jiangsu Province (CX10B–033Z), and Key Project
in Science and Technology Innovation Cultivation Program of
Soochow University.
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