Electronic Supplementary Material (ESI) for Chemical Communications. This journal is The Royal Society of Chemistry 2016
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1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material (ESI) for Chemical Communications This journal is The Royal Society of Chemistry 2016 Preparation and use of DMF stabilized Iridium Nanoclusters as methylation catalysts using methanol as the C1 source Kei Oikawa, Satoshi Itoh, Hiroki Yano, Hideya Kawasaki and Yasushi Obora* Department of Chemistry and Materials Engineering, Faculty of Chemistry, Materials and Bioengineering, Kansai University, Suita, Osaka , Japan E mail: obora@kansai u.ac.jp Table of Contents Chemicals and General experimental procedure... S2 Instrumental analysis of DMF stabilized Ir NCs... S3 7 Experimental procedure ( methylation and N methylation)... S8 Mechanism experiment and optimisation of N methylation... S10 12 References... S13 Copies of 1 H NMR, 13 C NMR spectra of compounds... S14 26
2 General GLC analysis was performed with a flame ionization detector using a 0.22 mm 25 m capillary column (BP 5). All NMR spectra were measured at 400 and 100 MHz, respectively, in CDCl 3 with TMS as an internal standard. All products were characterized by 1 H NMR, 13 C NMR and GC MS. The products yield were estimated from the peak areas based on the internal standard technique using GC. All starting materials were commercially available and used without any purification. Compounds 2a 1, 2b 2, 2c 3, 2d 2, 2e 4, 2f 1 2g 5, 2h 6, 2i 5, 2j 7, 5a 8, 5b 8 and 5c 8 were reported previously. High resolution mass spectra were performed at Global Facility Center, Hokkaido University. S2
3 Experimental Preparation of 0.1 M IrCl3 aq. (A) : A mixture of IrCl3(0.317 g) and distilled water (10 ml) was added to a vial bottle (10 ml), and allow the bottle to stand at room temperature overnight. Synthesis of DMF stabilized Ir NCs : DMF (50 ml) was added to a 300 ml three necked round bottom flask, and the solution was preheated to 140 o C (± 2 o C) and stirred 1300 to 1500 rpm for 5 min. Then the 0.1 M IrCl 3 solution (A) was added to the hot DMF solution, which allowed to react for 10 h on stirring (1300 rpm 1500 rpm) at 140 o C (± 2 o C). The resulting clear red solution was used as 1 mm Ir NCs solution in DMF for further reaction. After vacuum evaporation of the solvent, the residue was re dissolved in selected solvents such as DMF, D 2 O, MeOH for the dynamic light scattering (DLS), NMR measurement and the methylation reactions. S3
4 Optical spectroscopy of DMF stabilized Ir NCs : UV visible absorption spectra were measured by using a JASCO V 670 spectrophotometer. Fluorescence emission spectra were measured by using JASCO FP 6200 fluorescence spectrophotometer at UV excitation of 350 nm. Light Emitting Fig.S1 photoluminescent by UV lamp (350 nm) 2 UV 70 Fluorescence 60 Absorbance (logε) PL Intensity (a.u.) Wavelength (nm) Wavelength (nm) Fig. S2 (a) UV visible absorption spectra of DMF stabilized Ir NCs (red), and IrCl 3 as precursor (blue). (b) Photoluminescence emission spectra of DMF stabilized Ir NCs (red), and IrCl 3 as precursor (blue) S4
5 Fig. S3 DMF stabilized Ir NCs size distributions by TEM image Fig. S4 1 H NMR of DMF stabilized Ir NCs 1H NMR of DMF-stabilized Ir NCs (20, 400MHz) Ir NCs (in D2O, 70 mm): Sample A 8.15 D2O 2.84 Addition of a few drop of DMF to the Sample A (The peak of 7.92 ppm assigned to the formyl proton of free DMF) 7.92 D2O M S5
6 Fig. S5 XRD pattern of DMF stabilized Ir NCs Fig. S6 XPS spectra of DMF stabilized Ir NCs 3.5 x 10 4 XPS Intensity (arb. units) O KLL Binding Energy (ev) -C KLL -O1s -N1s -C1s -Cl2s -Cl2p -Si2s -Si2p -Ir4f7 -Ir4f5 -O2s S6
7 Fig. S7 FT IR of free DMF(blue) and DMF stabilized Ir NCs (orange) DMF C=O O-C-N DMF-Ir NCs Fig. S8 TG DTA for DMF stabilized Ir NCs TG DTA S7
8 A typical reaction procedure for Ir NCs catalyzed methylation of 1 phenylethanol 1a using methanol as C1 resource (Table 1, entry 12): A mixture of 1 phenylethanol 1a (122 mg, 1.0 mmol), cesium carbonate (675 mg, 3.0 mmol) and 1 mm Ir NCs in methanol (2.0 ml) as a catalyst was stirred at 150 o C for 24 h under Ar atmosphere. The conversions and yields of products 2a and 3a were estimated from peak areas based on an internal standard (methyl benzoate) using GC. The reaction mixture was extracted with diisopropylether (30 ml 2), dried over sodium sulfate, and evaporated under vacuum and the product was obtained in 87 % yield (130 mg) as yellow oil. A typical reaction procedure for Ir NCs catalyzed N methylation of aniline 4a using methanol as C1 resource (Table S2, entry 1): A mixture of aniline 4a (93 mg, 1.0 mmol), cesium carbonate (675 mg, 1.0 mmol) and 1 mm Ir NCs in methanol (2.0 ml) as a catalyst was stirred at 150 o C for 24 h under Ar atmosphere. The conversions and yields of product 5a were estimated from peak areas based on an internal standard (methyl benzoate) using GC and the product 5a were obtained in 87% yield. The reaction mixture was extracted with diisopropylether (30 ml 2), dried over sodium sulfate, and evaporated under vacuum and the product was obtained in 78% yield (84 mg) as yellow oil. Mercury poisoning test for Ir catalyzed methylation of 1 phenylethanol 1a using methanol: A mixture of 1 phenylethanol 1a (122 mg, 1.0 mmol), cesium carbonate (325 mg, 1.0 mmol), Hg (1 g, 5.0 mmol) and Iridium catalyst (0.001 mmol) in methanol (2.0 ml) was stirred at 150 o C for 24 h under Ar atmosphere. The conversions and yields of products 2a and 3a were estimated from peak areas based on an internal standard (methyl benzoate) using GC. S8
9 Compound 2k. Yield 54% (92 mg), colorless liquid; 1 H NMR δ (m, 4H), 3.69 (d, J = 8.0 Hz, 2H), (m, 1H), 1.43 (s, 1H), 1.26 (d, J = 8.0 Hz, 3H); 13 C NMR δ 145.8(C), 134.3(C), 129.9(CH), 127.4(CH), 126.7(CH), 125.7(CH), 68.4(CH 2 ), 42.1(CH), 17.4(CH 3 ); IR (neat, cm 1 ) 3300, 2929, 1597, 1570, 1429, 1082, 877, 783, 696; GC MS (EI) m/z (relative intensity) 170(24) [M + ], 139(100), 103(87), 77(34), 51(8), 39(4); HRMS (EI) m/z calcd for C 9 H 11 ClO: , found S9
10 Conditions screening of N methylation Table S2 Entry a Ir NCs (mol %) Conv. (%) GC Yield (%) > TON b a) Cs 2 CO 3 was used as base. b) Turnover number (TON) = 5a (mol)/irncs (mol) S10
11 Scheme S1. methylation of acetophenone with methanol using Ir NCs Scheme S2. Reaction with paraformaldehyde Table S3 Entry Conditions Conv. (%) GC Yield (%) A B C(2a) D(3a) 1 as above >99 n.d. a n.d. a without (HCHO) n 35 n.d. a 3 add Ir NCs (0.1 mol %) >99 n.d. a n.d. a trace trace n.d. a 12 n.d. a a) Not detected by GC. S11
12 Scheme S3. Hydrogen transfer capability of Ir NCs using methanol S12
13 References (1) S. Kobayashi, K. Shibakawa, Y. Miyaguchi and A. Masuyama, Asian J. Org. Chem., 2016, 5, (2) N. Kise, Y. Hirata and N. Ueda, J. Org. Chem., 2001, 66, (3) J. L. Jiang and Y. M. Zhang, Youji Huaxue, 1988, 8, (4) J. Farkaš and J. J. k. Novák, Collect. Czech. Chem. Commun. 1960, 25, (5) Y. Li, H. Li, H. Junge and M. Beller, Chem. Commun., 2014, 50, (6) S. Serra, Tetrahedron, Asymmetry, 2011, 22, (7) T. Morimoto, T. Fujii, K. Miyoshi, G. Makado, H. Tanimoto, Y. Nishiyama and K. Kakiuchi, Org. Biomol. Chem., 2015, 13, (8) T. T. Dang, B. Ramalingam and A. M. Seayad, ACS Catal., 2015, 5, S13
14 1 H NMR and 13 C NMR spectra 2a OH 5.00 M M S14
15 OH 2b S15
16 Cl OH 2c S16
17 2d and 3d (69:31) : M S17
18 OH 2e M M S18
19 OH 2g S19
20 OH 2h S20
21 OH 2i MeO M M S21
22 OH 2j S22
23 2k M S23
24 H N 5a S24
25 H N 5b S25
26 H N 5c Cl S26
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