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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information Copyright Royal Society of Chemistry. Self-assembled Pd 6 L 4 Cage and Pd 4 L 4 Square using hydrazide based ligands: Synthesis, characterisation and catalytic activity in Suzuki-Miyaura Coupling Reaction Subhashis Pradhan and Rohith P. John* Department of Applied Chemistry, Indian School of Mines, Dhanbad , Jharkhand, India Table of contents Figure S1: 1 H NMR of ligand L 1 in dmso-d 6... (p2) Figure S2: 13 C-NMR spectrum of the ligand L 1 in dmso-d 6... (p2) Figure S3: ESI-MS of L 1 equilibrium in dmso-d 6... (p3) Figure S4: 1 H NMR spectrum of L 2 in dmso-d 6... (p3) Figure S5: 13 C-NMR spectrum of the ligand L 2 in dmso-d 6... (p4) Figure S6: ESI-MS of L 2 equilibrium in dmso-d 6... (p4) Figure S7: 1 H NMR of Pd (2, 2 -bipyridyl)(no 3 ) 2 in dmso-d 6...(p5) Figure S8: 13 C NMR of Pd(2, 2 -bipyridyl)(no 3 ) 2 in dmso-d 6...(p5) Figure S9: 1 H NMR of 1 in dmso-d 6... (p6) Figure S10: 1 H- 1 H COSY spectrum of 1 in dmso-d 6... (p6) Figure S11: ESI-MS of 1 in dmso-d 6... (p7) Figure S12. ESI-MS spectra, expanded peaks of [2-12NO 3- +Na] 13+ and [2-8NO 3- ] 8+ ions.. (p7) Figure S13: 1 H NMR of 2 in dmso-d 6... (p8) Figure S14: 1 H- 1 H COSY spectrum of 2 in dmso-d 6... (p8) Figure S15: ESI-MS of 2 in dmso-d 6... (p9) Figure S16: ESI-MS spectra, expanded peaks of [2-6NO 3- +NH 4 ] 7+ and [2-4NO 3- ] 4+ ions.....(p9) Figure S17: Optimized structure of Td symmetric assembly 1. (p10) Figure S18: Optimized structure of square assembly 2. (p10) Figure S19a & 19b: ICP-AES of filtered reaction mixture of Suzuki coupling reactions catalyzed by 1 and 2... (p11) Figure S20a & 20b: EDX spectra and FE-SEM images of 1 and 2 after each reaction cycle (up to 2 nd cycle).. (p12) Figure 21: Suggested catalytic mechanism for the Suzuki-Miyaura cross-coupling reaction... (p13) Products of Suzuki-Miyaura coupling and their characterisation data (p14-p15) References (p15) 1 H & 13 C NMR data of the coupling products... (p16-p27) S1
2 Fig. S1. 1 H NMR of ligand L 1 in DMSO-d 6 (400 MHz) Fig. S2. 13 C-NMR spectrum of the ligand L 1 in DMSO-d 6 (100MHz) S2
3 Fig. S3. ESI-MS of L 1 in DMSO Fig. S4. 1 H NMR spectrum of L 2 in DMSO-d 6 (400 MHz) S3
4 Fig. S5: 13 C-NMR spectrum of the ligand L 2 in DMSO-d 6 (100 MHz) Fig.S6 ESI-MS of L 2 in DMSO S4
5 Fig. S7. 1 H NMR of Pd II (2,2 -bipy)(no 3 ) 2 in DMSO-d 6 (400 MHz) Fig. S8. 13 C NMR of Pd II (2,2 -bipy)(no 3 ) 2 in DMSO-d 6 (100 MHz) S5
6 Fig. S9. 1 H NMR of cage 1 in DMSO-d 6 (400 MHz) Fig. S10. 1 H- 1 H COSY spectrum of 1 in DMSO-d 6 (400 MHz) S6
7 Fig.S11. ESI-MS of 1 in DMSO Fig. S12. ESI-MS spectra of [1-12NO 3- +Na] 13+ (Left) and [1-8NO 3- ] 8+ (Right, Experimental in black and their simulated spectra in red). S7
8 Fig.S13. 1 H NMR of square assembly 2 in DMSO-d 6 (400 MHz) Fig. S14. 1 H- 1 H COSY spectrum of square assembly 2 in DMSO-d 6 (400MHz) S8
9 Fig. S15. ESI-MS of 2 in DMSO Fig. S16. ESI-MS spectra of [2-6NO 3- +NH 4 ] 7+ (Left) and [2-4NO 3- ] 4+ (Right, Experimental in black and their simulated spectra in red). S9
10 Figure S17. Optimised structure and dimensions of T d -symmetric assembly 1. Figure S18. Optimised structure and dimensions of the square assembly 2. S10
11 Fig.S19a. ICP-AES of filtered reaction mixture of Suzuki coupling reactions catalysed by 1 Fig.S19b. ICP-AES of filtered reaction mixture of Suzuki coupling reactions catalysed by 2. S11
12 Fig.S20a. EDX spectra (top) and FE-SEM (bottom) images of 1 after each reaction cycle (up to 2 nd cycle) Fig.S20b. EDX (top) spectra and FE-SEM (bottom) images of 2 after each reaction cycle (up to 2 nd cycle) S12
13 Figure 21. Suggested catalytic mechanism for the Suzuki-Miyaura cross-coupling reaction. [1, 2] S13
14 Products of Suzuki-Miyaura coupling and their characterization data: Biphenyl (1): [2] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.59 (d, J=7.08Hz, 4H), 7.44 (t, J=6Hz, 4H), 7.34 (t, J=8Hz, 2H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , NC 4-Cyanobiphenyl (2): [2] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.74 (d, J=6.4Hz, 2H), 7.69 (d, J=8.4Hz, 2H), 7.57 (d, J=8.4Hz, 2H), 7.49 (t, J=6.8Hz, 2H) 7.43 (t, J=4.8Hz, 1H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , H 3 COC 4-Acetylbiphenyl (3): [2] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 8.03 (d, J=8Hz, 2H), 7.68 (d, J=8Hz, 2H), 7.63 (d, J=7.7Hz, 2H), 7.47(t, J=7.6Hz, 2H), 7.40 (t, J=4Hz, 1H), 2.64(s, 3H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , , Me 4-Methylbiphenyl (4): [3] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.57(d, J=8.4Hz, 2H), 7.49 (d, J=6.4Hz, 2H), 7.42 (t, J=7.6Hz, 2H), 7.32 (t, J=7.2Hz, 1H), 7.25(d, J=6.4Hz, 2H), 2.39(s, 3H). 13 C- NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , MeO 4-Methoxybiphenyl (5): [2] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.53 (t, J=8Hz, 4H), 7.41 (t, J=6.4Hz, 2H), 7.29 (t, J=7.6Hz, 1H), 6.98(d, J=6.4Hz, 2H), 3.84(s, 3H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , H 2 N 4-Aminobiphenyl (6): [3] White solid. Eluent: Petether/ethylacetate. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.53(d, J=5.2Hz, 2H), (m, 4H), 7.27(t, J=4.4Hz, 1H), 7.76(d, J=4.4Hz, 2H), 3.72(brs,2H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , tbu 4-tert-Butyl-biphenyl (7): [4] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3 25 C, TMS) 7.58 (d, J= 6Hz, 2H), 7.54 (d, J=6Hz, 2H), (m, 4H), 7.32(t, J=8Hz, 1H), 1.36(s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , 34.56, NC tbu 4'-tert-Butyl-biphenyl-4-carbonitrile (8): [4] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.69 (q, J=8Hz, 4H), 7.52 (q, J=8Hz, 4H), 1.36 (s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , , 34.71, S14
15 O tbu 1-(4'-tert-Butyl-biphenyl-4-yl)-ethanone (9): [4] White solid. Eluent: Petether/ethyl acetate. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 8.02 (d, J=4.8Hz, 2H), 7.67 (d, J=5.2Hz, 2H), 7.57 (d, J=4.4Hz, 2H), 7.49(d, J=4.8Hz, 2H), 2.62(s, 3H), 1.36(s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , , 34.67, 31.34, Me tbu 4'-tert-Butyl-4-methyl-biphenyl (10): [5] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) (m, 6H), 7.23 (d, J=8Hz, 2H), 2.38 (s, 3H), 1.35(s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , 34.54, 31.42, MeO tbu 4'-tert-Butyl-4-methoxy-biphenyl(11): [4] White solid. Eluent: Petether/dichloromethane. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.51 (t, J=6.8Hz, 4H), 7.44 (d, J=6.6Hz, 2H), 6.96 (d, J=6.8Hz, 2H), 3.84(s, 3H), 1.36(s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , 55.35, 34.50, H 2 N tbu 4'-tert-Butyl-biphenyl-4-ylamine (12): [6] White solid. Eluent: Petether/ethylacetate. 1 H-NMR (400 MHz, CDCl 3, 25 C, TMS) 7.47(d, J=8.4, 2H), (m, 4H), 6.74(d, J=6.4Hz, 2H), 3.73(brs, 2H), 1.34 (s, 9H). 13 C-NMR (100 MHz, CDCl 3, 25 C, TMS) , , , , , , , , 34.46, REFERENCES: [1] D. J. M. Snelders, G. van Koten, R. J. M. K.Gebbink, J.Am. Chem. Soc., 2009, 131, [2] Y. Dong, C. Zhao, J. Ma, Q. Liu, Y. Yu, P. Wang,Y. Li, Green Chem., 2013, 15, 3150 [3] Y.M.A. Yamada, S.M. Sarkar, Y. Uozumi, J. Am. Chem. Soc., 2012, 134, [4] H. Wang, L. Li, X.-F. Bai, W.-H. Deng, Z.-J. Zheng, K.-F. Yang, L.-W. Xu, Green Chem., 2013, 15, [5] R. Martinez, I.M. Pastor, M. Yus, Synthesis., 2014, 46, [6] G.G. Cash, B. Anderson, K. Mayoa, S. Bogaczyk, J.Tunkel, Mutation Research., 2005, 508, 170. S15
16 1 H-NMR and 13 C-NMR spectra of the products of Suzuki coupling reactions in CDCl 3 Table 1, Entry 1: S16
17 Table 1, Entry 2: S17
18 Table 1, Entry 3: S18
19 Table 1, Entry 4: S19
20 Table 1, Entry 5: S20
21 Table 1, Entry 6: S21
22 Table 1, Entry 7: S22
23 Table 1, Entry 8: S23
24 Table 1, Entry 9: S24
25 Table 1, Entry 10: S25
26 Table 1, Entry 11: S26
27 Table 1, Entry 12: S27
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