Supporting Information Synthesis of cyclometalated 1,3,5-triphenylpyrazole palladium dimer and its activity towards cross coupling reactions
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1 Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is The Royal Society of Chemistry 215 Supporting Information Synthesis of cyclometalated 1,3,5-triphenylpyrazole palladium dimer and its activity towards cross coupling reactions Ramesh Mamidala [a], Vanga Mukundam [a], Kunchala Dhanunjayarao [a], and Krishnan Venkatasubbaiah* [a] School of Chemical Sciences, National Institute of Science Education and Research (NISER), Institute of Physics Campus, Bhubaneswar-7515, rissa (India). Fax: ; Tel: ; Reagents and solvents were purified according to standard procedures. Palladium acetate, 1,3-diphenyl-1,3-propanedione and phenylhydrazine were purchased from Sigma-Aldrich. Glacial acetic acid was obtained from Spectrochem. All glassware including Schlenk tubes were cleaned using base bath (potassium hydroxide in isopropanol solution), and acid bath (hydrochloric acid in distilled water). In some instance we used hydrofluoric acid to clean the Schlenk tubes. The stir-bars were cleaned using aqua regia solution. All 4 MHz 1 H, 1 MHz 13 C spectra were recorded on a Bruker ARX 4 spectrometer operating at 4 MHz. All 1 H and 13 C NMR spectra were referenced internally to solvent signals. ESI mass spectra were recorded on Bruker, microtf-qii mass spectrometer. Elemental analyses were carried out by using a Thermo quest CE instrument model EA/11 CHNS- elemental analyzer. Single-crystal X-ray diffraction data were collected on a Bruker APEX-II diffractometer equipped with an xford Instruments low-temperature attachment. The data were collected at 296 K using, Mo-Kα radiation (.7173 Å). Crystallographic data for 1 and details of X-ray diffraction experiments and crystal structure refinements are given in Table 1. SADABS 1 absorption corrections were applied in both cases. 1 The structures were solved and refined with SHELX suite of programs. 2 All non-hydrogen atoms were refined with anisotropic displacement coefficients. The H atoms were placed at calculated positions and were refined as riding atoms. Crystallographic data for the structure of 1 have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) ; deposit@ccdc.cam.ac.uk).
2 Table S1: ptimization of Heck cross coupling reaction of Bromobenzene and Methyl acrylate using palladacycle a Entry Cat. (mol%) Base Solvent TBAB (mol%) Temp. ( C) Time (h) Yield b (%) TN d 1.1 K 2 C 3 DMF Trace K 2 C 3 DMF K 2 C 3 DMF K 2 C 3 DMF K 2 C 3 DMF K 3 P 4 DMF K 3 P 4 DMF K 3 P 4 DMF K 3 P 4 DMAc K 3 P 4.H 2 DMF K 3 P 4 DMF c K 3 P 4 DMAc K 3 P 4 DMF K 3 P 4 DMF K 3 P 4 NMP
3 a Reaction conditions: 1 equiv of bromobenzene, 2 equiv of Methyl acrylate, 2 equiv of base. TBAB : Tetrabutylammoniumbromide, DMAc : Dimethylacetamide, NMP : N-methyl-2- pyrrolidone; b Isolated yield after chromatography; c Biphenyl product was also observed. d Turn over number, based on number of moles of the isolated product;. Table S2 : Heck cross coupling reaction of Bromobenzene and Styrene using palladacycle a Entry Cat. (mol%) Base Solvent TBAB (mol%) Temp. ( C) Time (h) Yield b (%) TN c 1.1 K 2 C 3 DMF K 3 P 4 DMF K 3 P 4 NMP a Reaction conditions: 1 equiv of Bromobenzene, 2 equiv of Styrene, 2 equiv of base; b Isolated yield after chromatography. c Turn over number, based on number of moles of the isolated product Table S3 : Heck cross coupling reaction of iodobenzene and methyl acrylate using palladacycle (1) Entry Base Solvent Temp. ( C) Time (h) Yield c (%) TN d 1 a K 2 C 3 DMF X a K 3 P 4 NMP X b K 2 C 3 DMF X e K 2 C 3 NMP a Reaction conditions: 2.45 mmol of iodobenzene, 4.9 mmol of methylacrylate, 4.9 mmol of base and 1.2 X 1-6 mmol of precatalyst 1 in 4 ml solvent
4 b Reaction conditions: 2.45 mmol of iodobenzene, 4.9 mmol of methylacrylate, 4.9 mmol of base X 1-6 mmol of precatalyst in 4 ml solvent c Isolated yield after chromatography d Turn over number (TN), based on number of moles of the isolated product e Reaction conditions: 2.45 mmol of iodobenzene, 4.9 mmol of methylacrylate, and 4.9 mmol of base Characterization data of the products in Table 2 and Table 3: White solid (m.p.37 C), HR-MS (ESI): calcd. for C 1 H 1 2 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.7 (d, J = 16 Hz, 1H, CH=CH), 4-1 (m, 2H, ArH), 7.39 (t, J = 4 Hz, 3H, ArH), 6.45 (d, J = 16 Hz, 1H, CH=CH), 3.81 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 134.4, 13.3, 128.9, 128.8, , White solid (m.p. 92 C), HR-MS (ESI): calcd. for C 11 H 12 3 ([M + Na] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.66 (d, J = 16 Hz, 1H, CH=CH), 7.48 (d, J = 8 Hz, 2H, ArH), 6.91 (d, J = 8 Hz, 2H, ArH), 6.32 (d, J = 16 Hz, 1H, CH=CH), 3.83 (s, 3H, Me), 3.77 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , 161.4, 142, , 127.1, , , 55.34, 55. White solid (m.p.148 C), HR-MS (ESI): calcd. for C 16 H 14 2 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.75 (d, J = 16 Hz, 1H, CH=CH), (m, 6H, ArH), (t, J = 8 Hz, 2H, ArH), (t, J = 8 Hz, 2H, ArH), 6.49 (d, J = 16 Hz, 1H, CH=CH), 3.83 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = 16, , 143.9, 14.15, , , 128.6, , 126, 127.6, ,
5 1 H NMR (4 MHz, CDCl 3 ) δ = 8. (d, J = 16 Hz, 1H, CH=CH), (d, J = 8 Hz, 1H, ArH), 7.35 (t, J = 8 Hz, 1H, ArH), (m, 2H, ArH), 6.53 (d, J = 16 Hz, 1H, CH=CH), 3.88 (s, 3H, Me), 3.8 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 14.3, 13, , , 12.7, , , 55.47, White solid (m.p.49 C), HR-MS (ESI): calcd. for C 12 H 14 2 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.64 (d, J = 16 Hz, 1H, CH=CH), 7.13 (s, 2H, ArH), 7.1 (s, 1H, ArH), 6.36 (d, J = 16 Hz, 1H, CH=CH), 3.8 (s, 3H, Me), 2.32 (s, 6H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = 164, , , , 132.1, , , 58, Light yellow solid (m.p.76 C), HR-MS (ESI): calcd. for C 11 H 9 2 F 3 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.69 (d, J = 16 Hz, 1H, CH=CH), (m, 4H, ArH), 6.5 (d, J = 16 Hz, 1H, CH=CH), 3.81 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , , , , 12.36, White solid (m.p.59 C), HR-MS (ESI): calcd. for C 11 H 12 2 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 7.7 (d, J = 16 Hz, 1H, CH=CH), 7.44 (d, J = 8 Hz, 2H, ArH), 7.21 (d, J = 8 Hz, 2H, ArH), 6.42 (d, J = 16 Hz, 1H, CH=CH), 3.82 (s, 3H, Me), 2.39 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 14.72, , , 128.8, 116.7, 51.62,
6 White solid (m.p.16 C), HR-MS (ESI): calcd. for C 11 H 9 2 N ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = (m, 5H), 6.5 (d, J = 16 Hz), 3.81 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , , , , , White solid (m.p.124 C). 1 H NMR (4 MHz, CDCl 3 ) δ = (m, 4H, ArH), (m, 6H, ArH), (.m, 2H, CH=CH). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , White solid (m.p.134 C), HR-MS (ESI): calcd. for C 15 H 14 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = (m, 4H, ArH), 7.37 (t, J = 8 Hz, 2H, ArH), (t, J = 8 Hz, 1H, ArH), 7.12 (d, J = 16 Hz, 1H,CH=CH), 6.98 (d, J = 16 Hz, 1H,CH=CH), 6.93 (d, J = 8 Hz, 2H, ArH), 3.85 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 13.18, , , , , , 126.3, , White solid (m.p.219 C). 1 H NMR (4 MHz, CDCl 3 ) δ = (m, 6H, ArH), 5 (d, J = 8 Hz, 2H, ArH), 7.46 (t, J = 8 Hz, 2H, ArH), (m, 3H, ArH), (m, 1H, ArH), 7.17 (s, 2H, CH=CH). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , , 128.7, 128.3, 122, , , , , ,
7 White solid (m.p.119 C), HR-MS (ESI): calcd. for C 15 H 11 N ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = (m, 6H, ArH), 7.4 (t, J = 8 Hz, 2H, ArH), 7.32 (t, J = 8 Hz, 1H, ArH), 7.2 (d, J = 16 Hz, 1H, CH=CH), 7.7 (d, J = 16 Hz, 1H, CH=CH). 13 C NMR (1 MHz, CDCl 3 ) δ = , 136.3, 131, , , , , , , 11, H NMR (4 MHz, CDCl 3 ) δ = (m, 4H, ArH), 7.36 (t, J = 8 Hz, 2H, ArH), (m, 2H, ArH), 7.13 (d, J = 16 Hz, 1H, CH=CH), 6.99 (t, J = 8 Hz, 1H, ArH), 6.92 (d, J = 16 Hz, 1H, CH=CH), 3.9 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , 128.6, , , , , 122, 12.77, 11.97, H NMR (4 MHz, CDCl 3 ) δ = 2 (d, J = 8 Hz, 2H, ArH), 7.37 (t, J = 8 Hz, 2H, ArH), (t, J = 8 Hz, 1H, ArH),, 7.16 (s, 2H, ArH), (m, 2H, CH=CH), 6.93 (s, 1H, ArH), 2.36 (s, 6H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , 128.2, , , , , , Light yellow solid (m.p.144 C). 1 H NMR (4 MHz, CDCl 3 ) δ = 7.96 (d, J = 8 Hz, 2H, ArH), (m, 4H, ArH), 7.39 (t, J = 8 Hz, 2H, ArH), 7.31 (t, J = 8 Hz, 1H, ArH), 7.23 (d, J = 16 Hz, 1H, CH=CH), 7.13 (d, J = 16 Hz, 1H, CH=CH), 2.61 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = 193, 142.3, , , , 128.9, , , , , ,
8 White solid (m.p.136 C). 1 H NMR (4 MHz, CDCl 3 ) δ = 9 (s, 4H, ArH), 2 (d, J = 8 Hz, 2H, ArH), 7.37 (t, J = 8 Hz, 2H, ArH), 7.29(t, J = 8 Hz, 1H, ArH), 7.18 (d, J = 16 Hz, 1H, CH=CH), 7.12(d, J = 16 Hz, 1H, CH=CH). 13 C NMR (1 MHz, CDCl 3 ) δ = 14.82, , , , , , 126.8, , 125.7, , , 129. White solid (m.p.122 C). 1 H NMR (4 MHz, CDCl 3 ) δ = 5 (d, J = 8 Hz, 2H, ArH), 7.46 (d, J = 8 Hz, 2H, ArH), 7.4 (t, J = 8 Hz, 2H, ArH),, (m, 4H, ArH), (m, 2H, CH=CH), 2.41 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = 135, 138, , , , , , , , White solid (m.p.89 C). 1 H NMR (4 MHz, CDCl 3 ) δ = (m, 4H, ArH), (m, 2H, ArH), (m, 1H, ArH), (m, 2H, ArH), 3.9 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , 14.91, 14.87, , , , , , , White solid (m.p.211 C). 1 H NMR (4 MHz, CDCl 3 ) δ = (m, 8H, ArH), 7.49 (t, J = 8 Hz, 4H, ArH), 7.39 (t, J = 8 Hz, 3H, ArH). 13 C NMR (1 MHz, CDCl 3 ) δ = 14.74, 14.15, , 124, ,
9 White solid (m.p.88 C), HR-MS (ESI): calcd. for C 13 H 9 N ([M + H] + ) : 18.88, found : H NMR (4 MHz, CDCl 3 ) δ = (m, 4H, ArH), 7.6 (d, J = 8 Hz, 2H, ArH), (m, 3H, ArH). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 139.2, 132.6, , , , , , H NMR (4 MHz, CDCl 3 ) δ = 4 (d, J = 8 Hz, 2H, ArH), 7.42 (t, J = 8Hz, 2H, ArH), (m, 3H, ArH), (m, 2H, ArH), 3.82 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , 155.6, 136, 13.91, 13.74, 126, , , , 12.84, , H NMR (4 MHz, CDCl 3 ) δ = 7.62 (d, J = 8 Hz, 2H, ArH), 7.46 (t, J = 8 Hz, 2H, ArH), 7.37 (m, 1H, ArH), 7.25 (s, 2H, ArH), (s, 1H, ArH), 2.43 (s, 6H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , , , 127.1, , H NMR (4 MHz, CDCl 3 ) δ = 8.4 (d, J = 8 Hz, 2H, ArH), (m, 4H, ArH), (t, J = 8 Hz, 2H, ArH), (m, 1H, ArH), 2.67 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = 197.8, 145.8, , , , , , , ,
10 White solid (m.p.69 C). 1 H NMR (4 MHz, CDCl 3 ) δ = 7.71 (s, 4H, ArH), 7.62 (d, J = 8 Hz, 2H, ArH), (m, 3H, ArH). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 129., 128.2, , 127.3, , White solid (m.p.49 C). 1 H NMR (4 MHz, CDCl 3 ) δ = 7.65 (d, J = 8 Hz, 2H, ArH), 4 (d, J = 8 Hz, 2H, ArH), 7.49 (t, J = 8 Hz, 2H, ArH), 7.39 (t, J = 8 Hz, 1H, ArH),, 7.32 (d, J = 8 Hz, 2H, ArH),, 2.46 (s, 3H, Me). 13 C NMR (1 MHz, CDCl 3 ) δ = , , 137.6, 123, , 127.4, 127.2, White solid (m.p.6 C), HR-MS (ESI): calcd. for C 13 H 1 ([M + H] + ) : , found : H NMR (4 MHz, CDCl 3 ) δ = 1.7 (s, 1H, CH), 7.94 (d, J = 8 Hz, 2H, ArH), 7.76 (d, J = 8 Hz, 2H, ArH), 7.65 (d, J = 8 Hz, 2H, ArH), (m, 3H, ArH). 13 C NMR (1 MHz, CDCl 3 ) δ = , , , , 13.29, 129.3, , , Reference:
11 1. G. M. Sheldrick, SADABS Program for Correction of Area Detector Data; University of Go ttingen: Go ttingen, Germany, SHELXTL, Package v. 6.1, BrukerAXS, Madison and WI. Molecular Structure of 1,3,5-triphenyl pyrazole 1 H NMR of 1,3,5-triphenyl pyrazole
12 ppm ppm pz 3 C NMR of 1,3,5-triphenyl pyrazole ppm
13 HRMS oof 1,3,5-triphenyl pyrazzole 1 H NMR R of Palladaccycle (1) 13 C NMR R of Palladacycle (1)
14 * mino or isomer CH2Cl2 * * * * * * 12 HRMS oof Palladacyccle (1) 1 H& 13 C NMR of the t isolated products * * 11 * 1 ppm *
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