Supplementary data
Vasant S. Borude, Rikhil V. Shah, Sanjeev R. Shukla*
Dept. of Fibres and Textile Processing Technology,
Institute of Chemical Technology (University under Section-3 of UGC Act 1956)
Matunga, Mumbai 400019, India.
Tel: (+) 91-22-2414 5616; Fax: (+) 91-22- 2414 5614;
E-mail: srshukla19@gmail.com
Table of Contents
1. General
----- 01
2. Characterization data of Compounds 3a-h
----- 02
3. References
----- 17
General:
All the solvents and chemicals were procured from S. D. Fine Chemicals (India) and were
used without any further purification. Merrifield polymer (4.3 mmol Cl/g resin and 2 %
cross-linked with divinylbenzene) was pro-cured from Fluka Pvt. Ltd. The reactions were
monitored by TLC using 0.25 mm E-Merck silica gel 60 F254 pre-coated plates, which
were visualized with UV light. The 1H NMR and 13C NMR spectra were recorded at 300
MHz and 75 MHz, respectively, on a Varian Mercury Plus spectrometer (VARIAN,
USA). Chemical shifts are expressed in δ (ppm) using TMS as an internal standard. FT-IR
spectra were recorded on Shimadzu 8400S FT-IR spectrophotometer. Thermogravimetric
analysis (TGA) was performed using a DTG-60H instrument (Shimadzu) in nitrogen
atmosphere between 25 and 500 ⁰C with a heating rate of 10 ⁰C/min. The copper content
in the polymer-supported catalyst was determined by atomic absorption spectroscopy
(AAS) (model GBC 932 plus, Australia). Inductively coupled plasma atomic emission
spectroscopy (ICP-AES) was performed on an ARCOS system from M/s. Spectro,
Germany.
Spectra data:
Table-3 Entry 3a:1, 2-diphenylethyne1
FT-IR (neat, cm–1): 3062, 2921, 2248, 1598, 1490, 1442, 1070, 916, 754; 1H NMR (300
MHz, CDCl3, δ ppm): 7.40 (d, J = 8.7 Hz, 4H), 7.59-7.63 (m, 6H);
13
C NMR (75 MHz,
CDCl3, δ ppm): 89.4, 123.3, 128.3, 128.4, 131.6.
Table-3 Entry 3b:1-methyl-3-(phenylethynyl)benzene2
FT-IR (neat, cm–1): 3056, 2921, 2852, 2206, 1600, 1492, 1442, 781, 752, 686; 1H NMR
(300 MHz, CDCl3, δ ppm): 2.39 (s, 3H), 7.17-7.45 (m, 6H), 7.56-7.59(m, 3H); 13C NMR
(75 MHz, CDCl3, δ ppm): 21.2, 89.0, 89.6, 123.1, 123.4, 128.1, 128.2, 128.3, 128.6,
129.1, 131.5, 132.2, 138.0.
Table-3 Entry 3c:1-methyl-4-(phenylethynyl)benzene6
FT-IR (neat, cm–1): 3051, 2918, 2216, 1913, 1593, 1508, 1440, 1180, 1070, 1016, 817,
754, 688; 1H NMR (300 MHz, CDCl3, δ ppm): 2.42(s, 3H), 7.21(d, J = 7.8Hz, 2H), 7.377.42 (m, 3H), 7.50 (d, J = 8.1Hz, 2H), 7.60 (dd, J = 7.8Hz, 2H);
13
C NMR (75 MHz,
CDCl3, δ ppm): 21.5, 88.8, 89.6, 120.3, 123.5, 128.1, 128.3, 129.1, 131.5, 131.6, 138.4.
Table-3 Entry 3d:1-methoxy-3-(phenylethynyl)benzene3
FT-IR (neat, cm–1): 2939, 2852, 2216, 1853, 1579, 1492, 1321, 1232, 1035, 929, 862, 767,
684; 1H NMR (300 MHz, CDCl3, δ ppm): 3.85(s, 3H), 6.92 (dd, J = 3.6, 8.1 Hz, 3H),
7.12-7.41 (m, 6H);
13
C NMR (75 MHz, CDCl3, δ ppm): 55.2, 89.2, 89.3, 114.9, 116.4,
123.2, 124.2, 124.3, 128.3, 128.3, 129.4, 131.6, 159.4.
Table-3 Entry 3e:1-methoxy-4-(phenylethynyl)benzene2
FT-IR (neat, cm–1): 2923, 2214, 1593, 1508, 1438, 1286, 1245, 1172, 1107, 1024, 914,
835; 1H NMR (300 MHz, CDCl3, δ ppm): 3.84 (s, 3H), 6.90 (d, J = 8.7 Hz, 2H), 7.35-7.39
(m, 3H), 7.50-7.57 (m, 4H) ; 13C NMR (75 MHz, CDCl3, δ ppm): 55.2, 88.1, 89.4, 114.0,
115.4, 123.6, 127.9, 128.3, 131.4, 133.0, 159.6.
Table-3 Entry 3f:1-fluoro-4-(phenylethynyl)benzene4
FT-IR (neat, cm–1): 3060, 2923, 2871, 2216, 1890, 1591, 1508, 1442, 1217, 1153, 1097,
1014, 837, 792, 752, 686; 1H NMR (300 MHz, CDCl3, δ ppm): 7.06 (t, J = 8.7Hz, 2H),
7.37 (t, J = 6.6, 7.5Hz, 3H), 7.52-7.57 (m, 4H); 13C NMR (75 MHz, CDCl3, δ ppm): 88.3,
89.0, 115.5, 119.4, 123.1, 128.3, 131.5, 133.4, 160.8, 164.1.
Table-3 Entry 3g:1-(4-(phenylethynyl)phenyl)ethanone5
FT-IR (neat, cm–1): 3255, 2881, 2217, 1677, 1600, 1402, 1352, 1182, 1068, 837, 759, 692;
1
H NMR (300 MHz, CDCl3, δ ppm): 2.60 (s, 3H), 7.34-7.38 (m, 3H), 7.53-7.62 (m, 4H),
7.92 (dd, J = 8.4Hz, 2H); 13C NMR (75 MHz, CDCl3, δ ppm): 88.6, 92.7, 122.6, 128.2,
128.2, 128.4, 128.8, 131.6, 131.7, 136.2, 197.3.
Table-3 Entry 3h: 2-(phenylethynyl)thiophene6
FT-IR (neat, cm–1): 3099, 2200, 1595, 1485, 1440, 1423, 1213, 1110, 916, 852, 752, 661;
1
H NMR (300 MHz, CDCl3, δ ppm): 7.04 (dd, J = 3.9, 4.8 Hz, 1H), 7.31-7.39 (m, 4H),
7.54-7.57 (m, 3H);
13
C NMR (75 MHz, CDCl3, δ ppm): 82.6, 93.0, 122.9, 123.3, 127.1,
127.2, 128.4, 128.4, 131.4, 132.5.
K1: Proton NMR
Table-3 Entry 3a: 1, 2-diphenylethyne
Table-3 Entry 3b:1-methyl-3-(phenylethynyl)benzene
Table-3 Entry 3c:1-methyl-4-(phenylethynyl)benzene
Table-3 Entry 3d:1-methoxy-3-(phenylethynyl)benzene
Table-3 Entry 3e:1-methoxy-4-(phenylethynyl)benzene
Table-3 Entry 3f:1-fluoro-4-(phenylethynyl)benzene
Table-3 Entry 3g: 1-(4-(phenylethynyl)phenyl)ethanone
Table-3 Entry 3h: 2-(phenylethynyl)thiophene
K2: Carbon NMR
Table-3 Entry 3a: 1, 2-diphenylethyne
Table-3 Entry 3b:1-methyl-3-(phenylethynyl)benzene
Table-3 Entry 3c:1-methyl-4-(phenylethynyl)benzene
Table-3 Entry 3d:1-methoxy-3-(phenylethynyl)benzene
Table-3 Entry 3e:1-methoxy-4-(phenylethynyl)benzene
Table-3 Entry 3f:1-fluoro-4-(phenylethynyl)benzene
Table-3 Entry 3g: 1-(4-(phenylethynyl)phenyl)ethanone
Table-3 Entry 3h: 2-(phenylethynyl)thiophene
K3: FT-IR Spectra
Table-3 Entry 3a: 1, 2-diphenylethyne
Table-3 Entry 3b:1-methyl-3-(phenylethynyl)benzene
Table-3 Entry 3c:1-methyl-4-(phenylethynyl)benzene
Table-3 Entry 3d:1-methoxy-3-(phenylethynyl)benzene
Table-3 Entry 3e:1-methoxy-4-(phenylethynyl)benzene
Table-3 Entry 3f:1-fluoro-4-(phenylethynyl)benzene
Table-3 Entry 3g: 1-(4-(phenylethynyl)phenyl)ethanone
Table-3 Entry 3h: 2-(phenylethynyl)thiophene
References:
1. Xie C, Liu L, Zhang Y, Xu P (2008) Org Lett 10:2393
2. Novak Z, Nemes P, Kotschy A (2004) Org Lett 6:4917
3. Wardrop DJ, Komenda JP (2012) Org Lett 14:1548
4. Xie C, Liu L, Zhang Y, Xu P (2008) Org Lett 10:2393
5. Zhang WW, Zhang XG, Li JH (2010) J Org Chem 75:5259
6. Moon J, Jeong M, Nam H, Ju J, Moon JH, Jung HM, Lee S (2008) Org Lett 10:945