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1 Supporting Information Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand Taemoon Song, Ji Eun Park, and Young Keun Chung * Department of Chemistry, College of Natural Sciences, Seoul National University, Seoul 08826, Republic of Korea Table of Contents I. Screening for Imine Synthesis: Table S1. Ligands S2 Table S2. Bases S2 Table S3. Solvents S3 Table S4. Amount of benzyl alcohol S3 Table S5. Reaction temperature and time S4 Table S6. Amounts of [Rh(COD)Cl] 2, xantphos, and bases S4 II. Screening for ester synthesis: Table S7. Oxidants and ligands S5 Table S8. Nitroarenes S5 Table S9. Bases S6 Table S10. Solvents S6 Table S11. Reaction temperature and time S7 Table S12. Amounts of [Rh(COD)Cl] 2 and Cs 2 CO 3 S7 III. Computational calculations: Fig S1. Comparison of relative free energy. S8 Table S13. Energies of local minimum stationary points. S9 Table S14. Atomic coordinates for stationary points. S9 IV. NMR Spectra of Isolated Products S18 V. References S55 S1
2 I. Screening for imine synthesis Table S1. Screening of ligands Table S2. Screening of bases S2
3 Table S3. Screening of solvents Table S4. Screening of the amount of benzyl alcohol used S3
4 Table S5. Screening of reaction temperature and time Table S6. Screening of the amounts of [Rh(COD)Cl] 2, xantphos, and bases S4
5 II. Screening for ester synthesis Table S7. Screening of oxidants and ligands Table S8. Screening of nitroarenes S5
6 Table S9. Screening of bases Table S10. Screening of solvents S6
7 Table S11. Screening of reaction temperature and time Table S12. Screening of the amounts of [Rh(COD)Cl] 2 and Cs 2 CO 3 S7
8 III. Computational calculations Computational details. The calculations were performed using the Gaussian 09 program package. 1 All the results were obtained at the DFT level of theory using the B3LYP hybrid functional. 2 The Rh atom uses the basis set of LANL2DZ+ECP. 3 The standard 6-31G(d,p) basis set was used for the remaining atoms. Solvent effect was taken into account by polarizable continuum model (PCM). 4 All geometries of stationary states were fully optimized without any symmetry restriction. Frequency calculations were performed to characterize the stationary points as minima states and to obtain the zero-point energies (ZPE) and thermal corrections at K. Fig S1. Comparison of relative free energy. S8
9 Table S13. Energies of local minimum stationary points. E 0 1 E 2 H a.u a.u a.u a.u I III benzaldehyde II/aldehyde II IV/aldehyde IV_R IV/PhCH 2 O IV/PhNH E 0 = E elec + ZPE 2. E = E 0 + E vib + E rot + E trans 3. H = E + RT 4. G = H TS G Table S14. Atomic coordinates for stationary points. S9
10 Benzaldehyde Atomic Number Coordinates (Å) Coordinates (Å) Atomic X Y Z Number X Y Z I Atomic Number Coordinates (Å) S10 Atomic Coordinates (Å) X Y Z Number X Y Z
11 III Atomic Number Coordinates (Å) S11 Atomic Coordinates (Å) X Y Z Number X Y Z
12 II/aldehyde Atomic Number Coordinates (Å) S12 Atomic Coordinates (Å) X Y Z Number X Y Z
13 II Atomic Number Coordinates (Å) S13 Atomic Coordinates (Å) X Y Z Number X Y Z
14 IV/aldehyde Atomic Number Coordinates (Å) Atomic Coordinates (Å) X Y Z Number X Y Z S14
15 IV_R Atomic Number Coordinates (Å) Atomic Coordinates (Å) X Y Z Number X Y Z S15
16 IV/PhCH 2 O - Atomic Number Coordinates (Å) Atomic Coordinates (Å) X Y Z Number X Y Z S16
17 IV/PhNH - Atomic Number Coordinates (Å) Atomic Coordinates (Å) X Y Z Number X Y Z S17
18 IV. NMR Spectra of Isolated Products (E)-N,1-diphenylmethanimine (Scheme 2, 3aa) S18
19 (E)-N-phenyl-1-(p-tolyl)methanimine (Scheme 2, 3ba) S19
20 (E)-1-(4-methoxyphenyl)-N-phenylmethanimine (Scheme 2, 3ca) S20
21 (E)-1-(4-(tert-butyl)phenyl)-N-phenylmethanimine (Scheme 2, 3da) S21
22 (E)-1-(4-fluorophenyl)-N-phenylmethanimine (Scheme 2, 3ea) S22
23 (E)-1-(4-chlorophenyl)-N-phenylmethanimine (Scheme 2, 3fa) S23
24 (E)-1-(2-methoxyphenyl)-N-phenylmethanimine (Scheme 2, 3ga) S24
25 (E)-1-(3-fluorophenyl)-N-phenylmethanimine (Scheme 2, 3ha) S25
26 (E)-1-(3-methoxyphenyl)-N-phenylmethanimine (Scheme 2, 3ia) S26
27 (E)-1-phenyl-N-(p-tolyl)methanimine (Scheme 2, 3ab) S27
28 (E)-N-(4-methoxyphenyl)-1-phenylmethanimine (Scheme 2, 3ac) S28
29 (E)-N-(4-fluorophenyl)-1-phenylmethanimine (Scheme 2, 3ad) S29
30 (E)-N-(4-chlorophenyl)-1-phenylmethanimine (Scheme 2, 3ae) S30
31 (E)-N-(4-bromophenyl)-1-phenylmethanimine (Scheme 2, 3af) S31
32 (E)-1-phenyl-N-(m-tolyl)methanimine (Scheme 2, 3ag) S32
33 (E)-1-(4-fluorophenyl)-N-(4-methoxyphenyl)methanimine (Scheme 2, 3ec) S33
34 (E)-N-(4-fluorophenyl)-1-(4-methoxyphenyl)methanimine (Scheme 2, 3cd) S34
35 Benzyl benzoate (Scheme 3, 4a) S35
36 4-methylbenzyl 4-methylbenzoate (Scheme 3, 4b) S36
37 4-methoxybenzyl 4-methoxybenzoate (Scheme 3, 4c) S37
38 4-(tert-butyl)benzyl 4-(tert-butyl)benzoate (Scheme 3, 4d) S38
39 4-fluorobenzyl 4-fluorobenzoate (Scheme 3, 4e) S39
40 4-chlorobenzyl 4-chlorobenzoate (Scheme 3, 4f) S40
41 4-(trifluoromethyl)benzyl 4-(trifluoromethyl)benzoate (Scheme 3, 4g) S41
42 4-cyanobenzyl 4-cyanobenzoate (Scheme 3, 4h) S42
43 2-methylbenzyl 2-methylbenzoate (Scheme 3, 4i) S43
44 2-methoxybenzyl 2-methoxybenzoate (Scheme 3, 4j) S44
45 Benzo[d][1,3]dioxol-5-ylmethyl benzo[d][1,3]dioxole-5-carboxylate (Scheme 3, 4k) S45
46 3-phenylpropyl 3-phenylpropanoate (Scheme 3, 4l) S46
47 Octyl octanoate (Scheme 3, 4m) S47
48 2-methylbutyl 2-methylbutanoate (Scheme 3, 4n) S48
49 Neopentyl pivalate (Scheme 3, 4o) S49
50 Cyclohexylmethyl cyclohexanecarboxylate (Scheme 3, 4p) S50
51 S51
52 Naphthalen-1-ylmethyl 1-naphthoate (Scheme 3, 4q) S52
53 Furan-2-ylmethyl furan-2-carboxylate (Scheme 3, 4r) S53
54 3-fluorobenzyl 3-fluorobenzoate (Scheme 3, 4s) S54
55 3-methoxybenzyl 3-methoxybenzoate (Scheme 3, 4t) S55
56 V. References 1. Gaussian 09, Revision A.02, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone,; Mennucci, V. B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonne nberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Norm and, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. ECross,.; J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ӧ.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J.; Gaussian, Inc., Wallingford CT, (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37, 785. (b) Becke, A. D. Chem. Phys. 1993, 98, (c) Stephens, P. J.; Devlin, F.J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, (a) Miertus, S.; Scrocco, E.; Tomasi, J. Chem. Phys. 1981, 55, (b) Miertus, S.; Tomasi, J. Chem. Phys. 1982, 65, (c) Cossi, M.; Barone, V.; Cammi, R.; Tomasi, J. Chem. Phys. Lett. 1996, 255, (d) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, (e) Mennucci, B.; Cances, E.; Tomasi, J. J. Phys. Chem. B, 1997, 101, (f) Barone, V.; Cossi, M. J. Phys. Chem. A, 1998, 102, (g) Tomasi, J.; Mennucci, B.; Cances, E. J. Mol. Struct. THEOCHEM, 1999, 464, (h) Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, S56
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