Nano-ordered B-MCM-41: An efficient and recoverable solid ... · catalysts, organic...

Scientia Iranica C (2011) 18 (6), 1356–1364

Sharif University of Technology

Scientia IranicaTransactions C: Chemistry and Chemical Engineering

www.sciencedirect.com

Nano-ordered B-MCM-41: An efficient and recoverable solid acidcatalyst for three-component Strecker reaction of carbonylcompounds, amines and TMSCNM.G. Dekamin ∗, Z. Mokhtari, Z. KarimiPharmaceutical and Biologically-Active Compounds Research Laboratory, Department of Chemistry, Iran University of Science and Technology, Tehran,P.O. Box 16846-13114, Iran

Received 4 March 2011; revised 30 May 2011; accepted 27 August 2011

KEYWORDSNano-ordered borosilicate(B-MCM-41);

Multi-component reactions;Strecker reaction;α-amino nitriles;Carbonyl compounds;TMSCN.

Abstract The three-component Strecker reaction of a wide range of aldehydes or ketones and differentamines with trimethylsilyl cyanide (TMSCN) was efficiently catalyzed by the nano-ordered mesoporousborosilicate (B-MCM-41) at room temperature to afford the corresponding α-amino nitriles in highto quantitative yields in short reaction time. B-MCM-41 showed higher catalytic activity than Fe(III)-modified MCM-41 (Fe-MCM-41). Furthermore, the use of EtOH increased the rate of reaction remarkablycompared to CH2Cl2 or CH3CN. TheB-MCM-41 catalyst canbe recovered at least 4 timeswithout significantloss of its catalytic activity.

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1. Introduction

Multi-component Condensation Reactions (MCRs) haverecently received great interest, due to the formation of multi-bonds in a one pot reaction, high atom efficiency, mild and sim-plified conditions and environmentally benign friendliness [1].The Strecker reaction, which was reported initially in 1850,is the oldest known MCR and the most straightforward routefor the synthesis of α-amino acids on both lab and technicalscales. This reaction comprises a condensation of an aldehyde,ammonia and cyanide source, followed by subsequent hydrol-ysis of the resulting α-amino nitrile. Since the first synthe-sis of cyanohydrins by Winkler in 1832 and α-amino nitrilesby Strecker in 1850, α-functionalized nitriles have attractedconsiderable attention of organic chemists, due to the rich

∗ Corresponding author. Tel.: +98 21 7724 0284; fax: +98 21 7322 7703.E-mail address: [email protected] (M.G. Dekamin).

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chemistry of the cyano group (CN) [2]. In particular, α-aminonitriles are very important intermediates in the preparationof α-amino acids, 1,2-diamines and a variety of nitrogen-containing heterocycles, such as imidazoles or thiadiazoles [3].The classical Strecker reaction employed KCN as a cyanidesource in aqueous solution,which does have several drawbacks,such as the high toxicity of KCN and production of an alkalinereaction mixture [2]. The latter can severely affect the sensi-tive substrates and thus limit the scope of this valuable reac-tion. Due to these limitations, a variety of cyanide sources andmethods have been investigated; some of these are Bu3SnCN,Et2AlCN, (Et)2P(O)CN, CH3(OH)(CN)CH3, K2[Fe(CN)6] [4] and(CH3)3SiCN (TMSCN) [5]. Among these non-alkalimetal cyanidevariants, TMSCN has emerged as a very effective, relatively safeand easy-to-handle cyanide source for a nucleophilic additionto imines and carbonyl double bonds [2,5b–g].

Protocols based on TMSCN often require Bronsted or Lewisacid catalytic systems. Therefore, many homogeneous cata-lysts, such as BiCl3, NiCl2, RuCl3, RhI3, CeCl3, InI3, ThCl3.4H2O,GdCl3.6H2O, La(NO3)3.6H2O, Fe(Cp)2PF6, Cu(OTf)2, Ga(OTf)3,Pr(OTf)3 and I2, have been developed in recent years [6]. Toovercome problems associated with homogeneous catalysts,some simple heterogeneous catalysts, including Zr(HSO4)4 [7a],guanidine HCl [7b] and LiClO4 [7c], have also been introduced.However, supported heterogeneous catalysts demonstrateseveral intrinsic advantages over their homogeneous coun-terparts: additional reactants activation by support, high sur-face area, ease of product separation and catalyst reuse, lower

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M.G. Dekamin et al. / Scientia Iranica, Transactions C: Chemistry and Chemical Engineering 18 (2011) 1356–1364 1357

Scheme 1: Strecker reaction of carbonyl compounds and amines with TMSCNcatalyzed by B-MCM-41 1.

contamination of products, and process advantages throughreactor operation in continuous flow versus batch configura-tion on large scales [8]. Therefore, some heterogeneous cat-alytic systems have been developed for the Strecker reactionin more recent years. The examples include mesoporous Co(II)complex, scandium triflate or sulfonic acid silica interphasecatalysts, organic polymer-supported scandium triflate,poly(4-vinyl pyridine)-SO2 complex, cellulose sulfuric acid, sil-ica sulfuric acid, silica-supported heteropoly acid andmontmo-rillonite [9]. Along this line, modified mesoporous silicas basedmaterials (MCM), which are mainly characterized by one di-mensional and highly ordered channels, with tunable pore ra-dius from approximately 2–50 nm, very large specific surfaceareas (up to 2000 m2 g−1) and a mechanically stable structure,can serve as desirable heterogeneous catalysts. All the abovefeatures allow faster diffusion of guest molecules, especiallylarge molecules, in the host frameworks of the catalyst andmake the reactions faster and more selective [10]. Literaturesurveys show that aluminium-modified MCM-41 (Al-MCM-41)has been investigated for some organic transformations, in-cluding the Strecker reaction [10,11]. However, other mod-ified MCM, such as boron-MCM-41 (B-MCM-41) and Fe(III)-modified MCM-41 (Fe-MCM-41), have not been sufficientlyexplored as recoverable solid acid catalysts. Recently, we haveintroduced efficient protocols for cyanosilyation of carbonylcompounds with TMSCN [5b–g] and the protection of alcoholswith hexamethyldisilazane (HMDS) [12]. In continuation of ourinterest in developing efficient organic transformations usingsilylating reagents, in this paper, we wish to report nano-ordered B-MCM-41 1 as an efficient and selective solid acidcatalyst for the three-component Strecker reaction of carbonylcompounds, especially less reactive ketones, and amines withTMSCN (Scheme 1).

2. Results and discussion

To create the active sites of boron species for catalysis, themesoporous silicawasmodified by incorporating boron into thepore wall in the form of H3BO3 (Si/B = 20) during synthesisof its framework from Si(OEt)4. The obtained nano-orderedB-MCM-41 1 was characterized by FT IR and diffuse reflectancespectroscopy techniques, and the results were consistent withthose reported earlier [13–15].

The FT IR spectra of pure silica MCM-41 and B-MCM-41 have been shown in Figure 1. The peaks at ∼806 cm−1,∼960 cm−1, ∼1076 cm−1 with a shoulder at ∼1240 cm−1are ascribed to the symmetric stretching of Si–O–Si, Si–OHstretching mode and the asymmetric stretching of Si–O–Si,respectively. The introduction of boron in the modified MCM-41 is confirmed from the characteristic IR band at 1385 cm−1 forthree-coordinated boron. In addition, no band was found in the∼930 cm−1 or 1340 cm−1–1370 cm−1 region; typical of tetra-coordinated boron in the framework and extra-frameworkboron oxide or hydrated boron oxide species, respectively.These results demonstrate that the incorporated boron inthe MCM-41 framework is mainly in a trigonal environment.

Figure 1: FT-IR spectra of the synthesized MCM-41 and B-MCM-41 samples.(a) MCM-41; and (b) B-MCM-41.

Figure 2: Diffuse reflectance spectra of (a) MCM-41, and (b) B-MCM-41.

Therefore, a Lewis acid behavior for the synthesized B-MCM-41 is anticipated due to the electron-deficient nature of three-coordinated boron [14,15].

The diffuse reflectance spectra of MCM-41 and B-MCM-41materials have been shown in Figure 2. Purely siliceous MCM-41 does not show any significant absorbance band, whereasa very distinct and relatively sharp band at 194 nm wasobserved for B-MCM-41. This band can be ascribed to thepartial B–O charge transfer transitions. It is noteworthy that acompleted absorption band has not been recorded due to thespectrophotometer wavelength limit at 190 nm [13].

In order to obtain optimal reaction conditions, the reactionof 4-chlorobenzaldehyde 2a, aniline 3a and TMSCN (1.2equiv.), as a model reaction, was examined in CH2Cl2 at roomtemperature. The results have been summarized in Table 1. Itwas found that only a trace of the desired amino nitrile (4a)was formed in the absence of catalyst 1, even after 24 h (entry1, Table 1). A moderate yield of 50% was obtained after thesame time, when 75 mg of the pure MCM-41 per mmol of2a was used (entry 2, Table 1). However, the model reactionproceeded smoothly in the presence of catalytic amounts ofactive boron species in catalyst 1 to afford the desired product,4a, in a relatively short reaction time (entries 3–5, Table 1).On the other hand, Fe(III)-modified MCM-41 (Fe-MCM-41)required longer reaction time compared to B-MCM-41 underthe same conditions (entry 6, Table 1). Furthermore, The effectof other solvents, such as EtOHandCH3CNwas also investigated(entries 7 and 8, Table 1). Interestingly, the use of safer EtOH

1358 M.G. Dekamin et al. / Scientia Iranica, Transactions C: Chemistry and Chemical Engineering 18 (2011) 1356–1364

Table 1: Three-component Strecker reaction of 4-chlorobenzaldehyde 2a and aniline 3a with TMSCN by various catalystsa .

Entry Catalyst Amount of catalyst (mg) Solvent Time (h) Yieldb (%)

1 – – CH2Cl2 24 52 MCM-41 75 CH2Cl2 24 563 B-MCM-41 75 CH2Cl2 4.5 984 B-MCM-41 50 CH2Cl2 5 965 B-MCM-41 25 CH2Cl2 7 916 Fe-MCM-41 50 CH2Cl2 6 957 B-MCM-41 50 EtOH 1.5 988 B-MCM-41 50 CH3CN 5 899 B-MCM-41 50 – 8 79

a Reaction conditions: 4-Chlorobenzaldehyde 2a (1 mmol), aniline 3a (1 mmol), TMSCN (1.2 mmol), catalyst, solvent (1.5 mL), room temperature.b Isolated yield.

Scheme 2: Plausible mechanism for the Strecker reaction of carbonyl compounds (2) and amines (3) with TMSCN catalyzed by B-MCM-41 1.

afforded the desired product (4a) much faster and in higheryield compared to toxic solvents, such as CH3CN and CH2Cl2.This implies that the Lewis basic ethanol molecules can affectboth reaction intermediates (II, IV and V’a) and TMSCN toenhance the overall reaction rate remarkably (Scheme 2) [11].On the other hand, the model reaction was not completedin a reasonable time under solvent-free conditions (entry 9,Table 1).

Encouraged by these results, aromatic, heteroaromatic andaliphatic aldehydes or ketones with aromatic and aliphatic

amines were subjected to Strecker reaction under optimizedreaction conditions (B-MCM-41; 50 mg per mmol of carbonylcompound, 1.2 equiv. of TMSCN, r.t., EtOH). Table 2 showsthe scope of the reaction using a number of representativecarbonyl compounds and amines, wherein high to quantitativeyields of the corresponding α-amino nitriles 4 were isolatedwithin a short reaction time in all cases studied (entries1–23, Table 2). Upon completion of the reactions, the catalystwas removed from the reaction mixture simply by filtrationduring crystallization of the products, or their usual work-up.


Table 2: Three-component Strecker reaction of various carbonyl compounds and amines with TMSCN catalyzed by B-MCM-41 (Si/B = 20) under the optimizedconditionsa .

Entry Carbonyl compound (2) Amine (3) Product (4) Time (h) Yieldb (%) m.p. (°C) Lit. m.p. (°C)

1 1.5 98 116–114 110–112 [16]

2 2 96 63–61 63–66 [7a]

3 2 95 87–88 86–88 [9b]

4 1 98 Oil Oil [6d]

5 1 97 83–85 89–92 [9d]

6 1.5 98 98–100 112–114 [6c]

7 2 96 76–78 76–78 [6b]

8 4 93 69–70 72–74 [7a]

(continued on next page)


Table 2 (continued)


9 4 92 91–93 95–96 [16]

10 6 95 68–69 68–69 [16]

11 6 96 100–103 98–100 [6b]

12 7.5 87 Oil Oil [4]

13 6 98 157–159 164–166 [6b]

14 6.75 89 69–72 70–71 [4]

15 3.5 97 83–85 85–87 [9d]

16 1 97 83–85 –


Table 2 (continued)


17 1.5 98 114–116 –

18 3.75 92 104–106 102–104 [9d]

19 5 94 100–103 –

20 2.25 91 Oil Oil [6d]

21 2 90 Oil Oil [6d]

22 4.5 89 Oil Oil [6d]

23 5 96 209–211 –

24 10 min 0 (96c) Oil Oil [5b]

a All compounds are known and their structures were established from their spectral data and melting points as compared with literature values[4,6,7,9,16].

b Isolated yield.c Cyanosilylation product 5a was isolated.


In general, substrates containing electron-withdrawing groupsrequire shorter reaction time compared to those with electron-donating groups depending on the used amine. Furthermore,B-MCM-41 worked well with acid sensitive electron-richheterocyclic aldehydes, such as furfural and thiophene-2-carbaldehyde, to provide the corresponding products in highyields without formation of any polymerization products(entries 10, 11) [6]. On the other hand, ketones showlower reactivity under the optimized reaction conditions incomparison with aldehydes, due to more steric hindrancearound the carbonyl group of ketones (entries 13, 14) [6]. Tothe best of our knowledge, only a few studies on the Streckerreaction with ketones have been reported in the literatures[6,9a,16].

The use of EtOH demonstrated a further advantage overother investigated solvents, such as CH2Cl2, CH3CN, DMF andTHF [9,11,16]. In our hands, it was found that products havingmelting points higher than 60 °Cprecipitated out of the reactionmixture and therefore afforded higher yields. This factorovercomes even onto the nucleophilicity of the used amine.For instance, aniline 3a provided generally higher yields than4-methylaniline 3b and even benzyl amine 3c. To gain moreinsight into the mechanism, the reaction mixture was furthermonitored by TLC, using authentic samples of correspondingcyanohydrin trimethylsilyl ethers and imines [2,5a], in the caseof carbonyl compounds 2a, 2d, 2e, 2h and 2k and amine 3a.It was found that corresponding cyanohydrin trimethylsilylether products were not observed in the presence of primaryamines. However, some imine product containing both (E)- and(Z)-isomers was formed during the reaction time, which wascompletely converted to the desired products, 4a–w, after thetimes indicated in Table 2. Furthermore, the use of pyrrolidine3d, as a secondary amine, in the reaction of 2a did notafford the desired α-amino nitrile. However, the correspondingcyanohydrin trimethylsilyl ether, 5a, was produced in 96% yieldafter 10 min (entry 24) [9,11]. In an additional experiment, thecorresponding imine of the model reaction was treated with 1under the optimized reaction conditions. It was found that thedesired product, 4a, was obtained quantitatively (96%) after 1 h.These findings, along with substituent effects, all demonstratethat formation of the imine intermediate (III) is the key step inthe one-pot, three component Strecker reaction, catalyzed byB-MCM-41 [6,11] (Scheme 2).

To verify whether the catalytic performance of B-MCM-41in the Strecker reaction is heterogeneous or not, the followingexperiment was performed. A mixture of the model reactionwas filtered off after 45 min, and the filtrate was stirred furtherat r.t. It was found that only 20% of the desired product (4a)was obtained after 24 h. On the other hand, the reusabilityof B-MCM-41 was also investigated. The separated B-MCM-41catalyst in the model reaction was subjected to a further runafter a simple recovery process, including washing by EtOAcand subsequent drying at 50 °C. Quantitative conversion of 2awas observed and the average 95% isolated yield obtained over5 consecutive studied runs (Figure 3). This proves that nano-ordered B-MCM-41 is stable enough to serve as a solid acid andheterogeneous catalyst under optimal reaction conditions.

3. Conclusion

In summary, the nano-ordered B-MCM-41 catalyst has beendemonstrated to be an efficient, mild, safe and recoverable solidacid catalyst for one-pot synthesis of α-amino nitriles in highto excellent yields and purity. The other attractive featuresof this methodology are: short reaction time, simple work-upprocedure, the use of a low toxicity solvent, and an inexpensive,readily available, air and water-stable and recyclable catalyst.

Figure 3: Recyclability of B-MCM-41 catalyst in 5 consecutive runs forsynthesis of 4a.

4. Experimental

4.1. General

All chemicals and reagents were purchased from Merckand Aldrich and used without further purification, except forbenzaldehyde and aniline, for which fresh distilled sampleswere used. Analytical TLC was carried out using Merck0.2 mm silica gel 60 F-254 Al-plates. All yields refer to theisolated products after purification. B-MCM-41 and Fe-MCM-41were synthesized hydrothermally, according to the reportedprocedure, and characterized by FT IR spectroscopy [13–15].Products were characterized by spectroscopy data (IR, 1H NMRspectra) and melting points. FT IR spectra were recorded asKBr pellets on a Shimadzu FT IR-8400S spectrometer. Diffusereflectance spectra were recorded on a double beam UV-Vis. Shimadzu 2550 spectrophotometer. All diffuse reflectancespectra were recorded at room temperature against KBr, andwere plotted in terms of absorbance. 1HNMR (500MHz) spectrawere obtained using a Bruker DRX-500 Avance spectrometer.All 1H NMR spectra were run in CDCl3 solution, relativeto TMS (0.00 ppm), at ambient temperature. Melting pointswere determined using an Electrothermal 9100 apparatus anduncorrected.

4.2. General procedure for preparation of B-MCM-41 1

B-MCM-41 was synthesized using gels with the followingmolar composition: SiO2 : 0.05B2O3 : 0.10CTAB : 0.33NaOH :70H2O. In a 250 mL beaker, 2.8 g of cetyltrimethylammoniumbromide (CTAB) was added to a mixture of deionized water(100 mL), NaOH (0.8 g) and H3BO3 (0.5 g). The mixture wasconstantly stirred with a magnet at 50 °C until CTAB wascompletely dissolved. Then, 17.4 mL of tetraethyl orthosilicate(TEOS, >98%) was added dropwise to the mixture with stirringat 50 °C for 2 h. The obtainedmixture was then transferred intoa Teflon-lined autocave and heated to 150 °C for 48 h. The solidproductwas filtered,washedwith deionizedwater, and dried inair at 100 °C for 12 h. The organic cations in the channels wereremoved by calcination of samples at 550 °C for 6 h [13].

4.3. Typical procedure for the one-pot synthesis ofα-aminonitriles4a–w

TMSCN (1.2 mmol, 0.15 mL) was added to a mixture ofB-MCM-41 (1, 50 mg), carbonyl compound (2a–o, 1 mmol) andamine (3a–c, 1 mmol) in 96% EtOH (3 mL) at r.t. The mixture


was stirred at room temperature for an appropriate time. Aftercompletion of the reaction, as indicated by TLC, the reactionmixture was directly crystallized after addition of 96% EtOH(5 mL), in the case of solid products. In the case of viscoseproducts, the reaction mixture was filtered, and the organicsolvent was evaporated under reduced pressure to afford anessentially pure product in most cases. Further purification ofthe viscose products could be performed by silica gel columnchromatography (EtOAc-hexane, 1:10) (Table 2).

4.4. Reusability of B-MCM-411

The reusability of the catalyst was investigated in a consec-utive Strecker reaction of 4-chlorobenzaldehyde 2a and aniline3awith TMSCN. The reactions were carried out according to theabove general procedure for the synthesis of α-aminonitriles.At the end of each reaction, the separated catalyst was washedwith a fresh aliquot of EtOAc (3 × 5 mL), dried in an oven at50 °C and reused.

4.5. Selected spectroscopic data

2-(N-Anilino)-2-(4-chlorophenyl) acetonitrile 4a (Table 2,entry 1): White solid, m.p.: 114–116 °C; IR (KBr): υ = 3405,2928, 2232, 1609, 1522, 1458, 1260, 1080, 782 cm−1; 1H NMR(500 MHz, CDCl3): δ = 4.14 (br s, 1H), 5.46 (s, 1H), 6.81 (d,J = 8.1 Hz, 2H), 6.97 (t, J = 7.3 Hz, 1H), 7.32 (t, J = 7.7 Hz, 2H),7.47 (d, J = 8.3 Hz, 2H), 7.58 (d, J = 8.3 Hz, 2H) ppm [7a,16].

2-(N-Anilino)-2-(4-methoxyphenyl) acetonitrile 4i (Table 2,entry 9): White solid, m.p. 93–94 °C; IR (KBr): υ = 3328, 2925,2349, 1602, 1504, 1440, 1248, 1172, 754 cm−1; 1H NMR (500MHz, CDCl3): δ = 3.87 (s, 3H), 4.51 (br s, 1H), 5.39 (s, 1H), 6.81(d, J = 7.8 Hz, 2H), 6.92 (t, J = 7.4 Hz, 1H), 7.00 (d, J = 7.8 Hz,2H), 7.30 (t, J = 8.7 Hz, 2H), 7.53 (d, J = 8.7 Hz, 2H) ppm[4,7a,16].

2-(N-Anilino)-2-furyl acetonitrile 4j (Table 2, entry 10): Darkbrown solid, m.p. 67–69 °C; IR (KBr): υ = 3362, 3045, 2351,1602, 1556, 1490, 1311, 1161, 746 cm−1; 1H NMR (500 MHz,CDCl3): δ = 4.12 (br s, 1H), 5.52 (s, 1H), 6.44 (d, J = 4.7 Hz,1H), 6.61 (t, J = 4.7 Hz, 1H), 6.81 (d, J = 7.8 Hz, 2H), 6.96 (t,J = 7.8 Hz, 1H), 7.28 (t, J = 7.8 Hz, 2H), 7.51 (d, J = 4.7 Hz,1H) ppm [7a,16].

2-(N-Anilino)-2-(4-nitrophenyl) propanenitrile 4m (Table 2,entry 13): Yellow crystalline solid, m.p. 161–164 °C; IR (KBr):υ = 3382, 3068, 2942, 2246, 1923, 1691, 1604, 1515, 1346,1264, 1177, 1099, 852, 743, 692 cm−1; 1H NMR (500 MHz,CDCl3): δ = 2.0 (s, 3H), 4.48 (br s, 1H), 6.50 (d, J = 8.5 Hz,2H), 6.81 (t, J = 7.4 Hz, 1H), 7.11 (t, J = 7.5 Hz, 2H), 7.81 (d,J = 8.8 Hz, 2H), 8.25 (d, J = 8.8 Hz, 2H) ppm [16].

2-(4-Chlorophenyl)-2-(4-tolylamino) acetonitrile 4o (Table 2,entry15):White solid,m.p.: 83–85 °C; IR (KBr):υ = 3336, 2921,2356, 1620, 1515, 1490, 1093, 813 cm−1; 1H NMR (500 MHz,CDCl3): δ = 2.31 (s, 3H), 3.96 (br s, 1H), 5.41 (s, 1H), 6.71 (d,J = 7.9 Hz, 2H), 7.10 (d, J = 7.9 Hz, 2H), 7.46 (d, J = 8.4 Hz,2H), 7.57 (d, J = 8.3 Hz, 2H) ppm [6a].

2-(N-Benzylamino)-2-(4-chlorophenyl) acetonitrile 4t (Ta-ble 2, entry 20): Light yellow oil; IR (KBr): υ = 3323, 3029,2362, 1664, 1473, 1099, 725 cm−1; 1H NMR (500 MHz, CDCl3):δ = 2.0 (s, 1H), 3.75 (s, 2H), 4.75 (s, 1H), 7.28–7.42 (m, 5H), 7.53(d, J = 7.0 Hz, 2H), 7.52 (d, J = 7.0 Hz, 2H) ppm [16].

Acknowledgments

We are grateful for the financial support from The ResearchCouncil of IranUniversity of Science and Technology (IUST), Iran(Grant No. 160/5354). We would also like to acknowledge thesupport of The Iran Nanotechnology Initiative Council (INIC).

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Mohammad G. Dekamin was born in Nahavand, Iran, in 1972. He studiedChemistry at Shahid Chamran University, Ahwaz and received his B.S. Degreein 1995. Dr. Dekamin obtained his M.S. Degree in Organic Chemistry under thesupervision of Professor Mohammad S. Khajavi at Shahid Beheshti Universityin 1997, and completed his Ph.D. Degree in the same subject under the

supervision of Professor Firouz Matloubi Moghaddam at Sharif University ofTechnology (SUT), Tehran, in 2002. During the Ph.D. program (2001), Dr.Dekamin spent 8 months in the research group of Professor James H. Clark, inthe Clean Technology Center at York University in the UK as Visiting Scholar.He joined the faculty of the Department of Chemistry at Isfahan University ofTechnology in July 2003. InOctober 2004, hemoved to IranUniversity of Scienceand Technology (IUST), where he is currently Associate Professor of OrganicChemistry. His research interests involve green and environmentally-benignchemistry, heterogeneous catalysis and organo-catalysis, nanotechnology andpharmaceuticals. He has published over 30 research papers in journalspublished by Elsevier, Wiley-VCH, Royal Society of Chemistry (UK), Springer,Taylor & Francis, Chemical Society of Japan, Iranian Chemical Society, ScientiaIranica, etc.

Zahra Mokhtariwas born in 1983 in Tehran, Iran. She obtained her B.S. Degreein Chemistry fromKhajehNasir Toosi University of Technology, Tehran, in 2007.In 2008, she joined the research group of Dr. Mohammad G. Dekamin andcompletedherM.S. Degree inOrganic Chemistry in February, 2011.Her researchinterests include heterogeneous catalysis, synthetic methodologies based onsilylating reagents and nanotechnology.

Zahra Karimi was born in 1984 in Abhar, Iran. She completed her B.S. Degreein Chemistry at Imam Khomeini International University, Qazvin, in 2006.She joined the research group of Dr. Mohammad G. Dekamin in 2006 andcompleted her M.S. Degree in Organic Chemistry in 2008. She is now a Ph.D.Student at Bu-Ali Sina University, in Hamedan. Her research interests include:organocatalysis and heterogeneous catalysis, syntheticmethodologies based onsilylating reagents, nanotechnology and multi-component reactions.

Nano-ordered B-MCM-41: An efficient and recoverable solid acid catalyst for three-component Strecker reaction of carbonyl compounds, amines and TMSCNIntroductionResults and discussionConclusionExperimentalGeneralGeneral procedure for preparation of B-MCM-41 1Typical procedure for the one-pot synthesis of α -aminonitriles 4a--wReusability of B-MCM-411Selected spectroscopic data

AcknowledgmentsReferences

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