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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Supporting Information ortho-alkenylation of anilines with aromatic terminal alkynes over nanosized zeolite beta Mameda Naresh, a,b Peraka Swamy, a,b Kodumuri Srujana, a Chevella Durgaiah a, Marri Mahender Reddy a and Nama Narender *a,b a Academy of Scientific and Innovative Research,, CSIR-Indian Institute of Chemical Technology, Hyderabad , India b I&PC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad , India Tel.: ; Fax: / ; narendern33@yahoo.co.in; nama@iict.res.in Table of Contents. Experimental section S2 2. Spectroscopic data of all products....s3-s6 3. Copies of H and 3 C NMR spectra of all products. S7-S22 4. Notes and references.s22 S
2 . Experimental section I. General information All chemicals used were reagent grade and used as received without further purification. All the samples were systematically characterized by different spectroscopic techniques. The XRD patterns of the samples were obtained on a Regaku miniflux X-ray Diffractometer using Ni filtered CuKα radiation at 2θ = 2-80º with a scanning rate of 2º min - and the beam voltage and currents of 30 kv and 5 ma, respectively. H NMR spectra were recorded by using Bruker VX NMR FT-300 or Varian Unity 500 and 3 C NMR spectra were recorded by using Bruker VX NMR FT-75 MHz spectrometers instrument in CDCl 3. The chemical shifts ( ) are reported in ppm units relative to TMS as an internal standard for H NMR and CDCl 3 for 3 C NMR spectra. Coupling constants (J) are reported in hertz (Hz) and multiplicities are indicated as follows: s (singlet), d (doublet), dd (doublet of doublet), dt (doublet of triplet), t (triplet), m (multiplet). Column chromatography was carried out using silica gel ( mesh). II. General procedure for the ortho-alkenylation of anilines with aromatic terminal alkynes over nanosized zeolite beta Aniline (2 mmol), aromatic alkyne (2 mmol) and nanosized zeolite beta (00 mg) were added to ml of toluene in sealed vial and the reaction mixture was allowed to stir at 20 o C for 3 h. Than the reaction mixture was cooled to room temperature, diluted with ethylacetate. The catalyst was separated by filtration and the removal of solvent in vacuo yielded crude residue. The crude residue was further purified by column chromatography using silica gel ( mesh) to afford pure products. All the products were identified on the basis of H and C 3 NMR spectral data. S2
3 2. Spectroscopic data l-phenyl-l-(2-aminophenyl)ethylene (3a) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.54 (bs, 2 H), 5.35 (d, J =.34 Hz, H), 5.79 (d, J =.34 Hz, H), 6.69 (dd, J =.34, 7.94 Hz, H), 6.78 (dt, J =.22, 7.45 Hz, H), (m, 2 H), (m, 3 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 5.5, 6.04, 8.24, 26.56, 27.22, 28.0, 28.49, 28.69, 30.74, 39.57, 43.84, Phenyl-l-(2-amino-5-methoxyphenyl)ethylene (3b) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.29 (bs, 2 H), 3.75 (s, 3 H), 5.35 (d, J =.37 Hz, H), 5.80 (d, J =.22 Hz, H), 6.65 (d, J = 8.54 Hz, H), 6.72 (d, J = 2.89 Hz, H), 6.77 (dd, J = 2.89, 8.54 Hz, H), (m, 3 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 55.73, 4.56, 6.08, 6.2, 6.86, 26.58, 28.08, 28.55, 37.56, 39.36, 47.09, Phenyl-l-(2-amino-5-methylphenyl)ethylene (3c) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 2.26 (s, 3 H), 3.48 (bs, 2 H), 5.34 (d, J =.3 Hz, H), 5.78 (d, J =.3 Hz, H), 6.62 (d, J = 7.93 Hz, H), 6.93 (s, H), 6.97 (dd, J =.5, 7.93 Hz, H), (m, 5 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 20.35, 5.85, 5.69, 26.58, 27.4, 27.95, 28.47, 29.23, 3.3, 39.70, 4.34, Phenyl-l-(2-amino-3-methoxyphenyl)ethylene (3d) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.74 (bs, 2 H), 3.86 (s, 3 H), 5.36 (d, J =.37 Hz, H), 5.80 (d, J =.37 Hz, H), (m, 2 H), 6.80 (dd, J =.98, 7.32 Hz, H), (m, 3 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 55.53, 09.37, 5.93, 7.24, 22.84, 26.63, 27.2, 27.95, 28.46, 33.87, 39.60, 46.88, Phenyl-l-(2-amino-3-methylphenyl)ethylene (3e) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 2.7 (s, 3 H), 3.54 (bs, 2 H), 5.35 (d, J =.3 Hz, H), 5.8 (d, J =.5 Hz, H), 6.73 (t, J = 7.36 Hz, H), 7.00 (d, J = 6.60 Hz, H), 7.07 (d, J = 7.93 Hz, H), (m, 5 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 7.7, 6.06, 7.78, 22.34, 26.58, 28.0, 28.50, 28.60, 29.84, 39.7, 42.00, Phenyl-l-(2-amino-3, 5-dimethylphenyl)ethylene (3f) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 2.5 (s, 3 H), 2.24 (s, 3 H), 3.4 (bs, 2 H), 5.33 (d, J =.37 Hz, H), 5.79 (d, J =.37 Hz, H), 6.8 (s, H), 6.89 (s, H), (m, 3 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 7.68, 20.33, 5.93, 26.57, 27.97, S3
4 28.47, 28.90, 30.56, 39.43, MS (ESI): m/z = 224 (M + + H). Anal.Calcd for C 6 H 7 N C, 86.05; H, 7.67; N, 6.27; Found: C, 86.09; H, 7.6; N, Phenyl-l-(2-amino-5-chlorophenyl)ethylene (3g) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.54 (bs, 2 H), 5.36 (d, J =.66 Hz, H), 5.8 (d, J =.22 Hz, H), (m, H), (m, 2 H), (m, 5 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 6.63, 6.74, 22.79, 26.53, 28.3, 28.49, 28.65, 30.23, 38.88, 42.58, Phenyl-l-(2-amino-3-bromophenyl)ethylene (3h) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 4.03 (bs, 2 H), 5.36 (d, J =.32 Hz, H), 5.83 (d, J =.3 Hz, H), 6.65 (t, J =7.74 Hz, H), 7.06 (dd, J =7.74 Hz, H), (m, 6 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 09.66, 6.6, 8.58, 26.50, 28.2, 28.29, 28.63, 29.8, 3.97, 38.86, 4.66, MS (ESI): m/z = 274 (M + + H). Anal.Calcd for C 4 H 2 BrN C, 6.33; H, 4.4; N, 5.; Found: C, 6.30; H, 4.40; N, Phenyl-l-(2-amino-5-bromophenyl)ethylene (3i) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.55 (bs, 2 H), 5.35 (d, J =.05 Hz, H), 5.89 (d, J =.22 Hz, H), 6.57 (d, J = 9.5 Hz, H), (m, 2 H), (m, 5 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 09.84, 6.77, 7.02, 26.5, 28.3, 28.64, 29.02, 3.36, 32.99, 38.83, 43.05, Phenyl-l-(2-amino-5-nitrophenyl)ethylene (3j) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 4.28 (bs, 2 H), 5.44 (d, J = 0.9 Hz, H), 5.90 (d, J = 0.9 Hz, H), 6.64 (d, J = 9.46 Hz, H), (m, 5 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 09.38, 6.07, 7.29, 22.88, 26.69, 28.03, 28.52, 33.90, 39.64, Phenyl-l-(2-N-methylaminophenyl)ethylene (3m) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 2.7 (s, 3 H), 3.7 (bs, H), 5.33 (d, J =.37 Hz, H), 5.82 (d, J =.37 Hz, H), 6.65 (d, J = 8.24 Hz, H), 6.74 (td, J =.06, 7.47 Hz, H), 7.08 (dd, J =.67, 7.47 Hz, H) (m, 6 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 30.76, 09.93, 6.08, 6.60, 26.50, 28.0, 28.47, 28.9, 30.34, 39.66, 46.60, l-phenyl-l-(2-amino-l-anthryl)ethylene (3o) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.94 (bs, 2 H), 5.29 (s, H), 5.49 (d, J =.46 Hz, H), 6.33 (d, J =.46 Hz, H), 7.07 (d, J = 8.92 Hz, H), (m, 5 H), (m, 2 H), S4
5 (m, H) (m, 2 H), 8.08 (s, H), 8.29 (s, H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 6.7, 8.0, 9.86, 2.67, 23.94, 25.8, 26.8, 26.39, 27.65, 27.93, 28.08, 28.64, 29.22, 29.34, 32., 32.34, 39.06, 39.86, (-p-tolylvinyl)Aniline (3p) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 2.33 (s, 3 H), 3.55 (bs, 2 H), 5.30 (d, J =.52 Hz, H), 5.75 (d, J =.52 Hz, H), 6.69 (dd, J =.06, 8.08 Hz, H), 6.78 (dt, J =.06, 7.32 Hz, H), (m, 4 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 2.3, 5.7, 5.49, 8.24, 26.48, 28.48, 28.63, 29.22, 30.74, 36.72, 37.93, 43.88, MS (ESI): m/z = 20 (M + + H). Anal.Calcd for C 5 H 5 N C, 86.08; H, 7.22; N, 6.69; Found: C, 86.07; H, 7.2; N, (-(4-fluorophenyl)vinyl)Aniline (3q) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.55 (bs, 2 H), 5.33 (d, J =.06 Hz, H), 5.74 (d, J =.06 Hz, H), 6.70 (dd, J =.06, 8.08 Hz, H), 6.78 (dt, J =.06, 7.32 Hz, H), (m, 2 H) (dd, J =.67, 7.62 Hz, H), 7.6 (dt, J =.67, 8.08 Hz, H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 5.38 (J CF = Hz), 5.70 (J CF = 9.08 Hz), 8.35, 27.0, (J CF = 8.06 Hz), 28.86, 30.68, 35.72, 43.78, 46.07, (J CF = Hz). MS (ESI): m/z = 24 (M + + H). Anal.Calcd for C 4 H 2 FN C, 78.85; H, 5.66; N, 6.57; Found: C, 78.86; H, 5.66; N, (-(3-chlorophenyl)vinyl)Aniline (3r) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.55 (bs, 2 H), 5.40 (d, J =.22 Hz, H), 5.8 (d, J =.2 Hz, H), 6.70 (dd, J =.58, 7.58 Hz, H), 6.79 (dt, J =.0, 7.45 Hz, H), 7.08 (dd, J =.58, 7.58 Hz, H), (m, H), (m, 3 H), (m, H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 5.66, 7.27, 8.39, 24.86, 26.62, 28.06, 29.00, 29.75, 30.73, 34.53, 4.64, 43.79, 45.99, MS (ESI): m/z = 230 (M + + H). Anal.Calcd for C 4 H 2 ClN C, 73.20; H, 5.27; N, 6.0; Found: C, 73.20; H, 5.28; N, (-(4-bromophenyl)vinyl)aniline (3s) H NMR (300 MHz, CDCl 3 ): δ (ppm) = 3.56 (bs, 2 H), 5.37 (d, J =.22 Hz, H), 5.80 (d, J =.2 Hz, H), 6.70 (dd, J =.06, 8.08 Hz, H), 6.79 (dt, J =.22, 7.47 Hz, H), 7.07 (dd, J =.37, 7.47 Hz, H), (m, H), (m, 2 H), (m, 2 H). 3 C NMR (75 MHz, CDCl 3 ): (ppm) = 5.06, 6.56, 8.38, 22.9, 26.6, 28.23, 28.95, 30.72, S5
6 3.62, 38.54, 43.76, MS (ESI): m/z = 274 (M + + H). Anal.Calcd for C 4 H 2 BrN C, 6.33; H, 4.4; N, 5.; Found: C, 6.32; H, 4.42; N, 5.2. Figure S. XRD patterns of nanosized zeolite beta samples: (a) uncalcined; (b) calcined; (c) reused catalyst. S6
7 S7 NH 2
8 NH 2 O S8
9 S9 NH 2
10 O NH 2 S0
11 S NH 2
12 S2 NH 2
13 NH 2 Cl S3
14 Br NH 2 S4
15 NH 2 Br S5
16 NH 2 NO 2 S6
17 S7 NH
18 S8 NH 2
19 S9 NH 2
20 NH 2 F S20
21 NH 2 Cl NH 2 Br S2
22 Notes and references. A. Arienti, F. Bigi, R. Maggi, E. Marzi, P. Moggi, M. Rastelli, G. Sartori and F. Tarantola, Tetrahedron, 997, 53, S22
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