Acceptorless Dehydrogenation and Dehydrogenative Coupling of Alcohols. by Protic NHC Ruthenium Complexes
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Supporting Information for Acceptorless Dehydrogenation and Dehydrogenative Coupling of Alcohols by Protic NHC Ruthenium Complexes Weihong Chang, a Xue Gong, a,b Shuizhong Wang, a Ling-Ping Xiao a and Guoyong Song a* a Beijing Key Laboratory of Lignocellulosic Chemistry, Beijing Forestry University, No.35 Tsinghua East Road, Beijing , China. b School of Science, Beijing Forestry University, Beijing , China Contents 1 General Information S2 2 Catalytic reactions S2 3 X-ray structures and data of 2 and 4 S9 4 NMR spectra S13 1
2 1. General Information All reactions dealing with air- or moisture-sensitive compounds were performed by standard Schlenk techniques or in the nitrogen-filled Vigor glove box. Analytical thin-layer chromatography (TLC) was performed on HSGF254 silica gel plates. THF, xylene, toluene, diethyl ether and hexane were distilled from sodium and stored over fresh Na chips in a glovebox. 1 H and 13 C nuclear magnetic resonance (NMR) spectra of organic products were recorded on a Bruker AVIII 400 MHz spectrometer instrument. Data are reported as follows: chemical shift in ppm (δ), multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad signal), coupling constant (Hz), and integration. 2. Catalytic reactions General procedure for acceptorless dehydrogenation of alcohols: In a nitrogen-filled glovebox, 1- phenylethanol (120 mg, 0.98 mmol), complex 2 (5.5 mg, 1% mol), Cs 2 C 3 (3.2 mg, 1% mol) and xylene (1 ml) were charged in a seal bottle, which was heated at 140 o C. The reaction was monitored by GC-MS. After reaction, the solution was allowed to cool to room temperature, filtered through a silica gel column, and eluted with petroleum ether. The resulted solution was evaporated carefully under vacuum to afford acetophenone (100 mg, 85% yield). The 1 H NMR and MS spectra of acetophenone were matched with the previous reports. General procedure for dehydrogenative coupling of secondary alcohols with primary alcohols: In a nitrogen-filled glovebox, 1-phenylethanol (60 mg, 0.49 mmol), benzyl alcohol (55 mg, 0.51 mmol), complex 2 (5.5 mg, 2% mol), Cs 2 C 3 (3.2 mg, 2% mol) and xylene (1 ml) were charged in a seal bottle, which was heated at 150 o C for 48 h. After reaction, the solution was allowed to cool to room temperature. The pure product 8a was obtained as a white solid (87 mg, 85% yield) by column chromatography with petroleum ether/ethyl acetate (100:1) as eluent. 2
3 Table S1 ptimization of dehydrogenative coupling of 1-phenylethanol and benzyl alcohol Entry Cat. (2 mol%) Solution Temp ( ) Base GC Yield (%) 1 4 toluene 120 Cs 2 C xylene 150 Cs 2 C xylene 120 Cs 2 C xylene 150 none xylene 150 none xylene 150 Cs 2 C xylene 150 K t Bu xylene 150 Na t Bu xylene 150 NaAc 0 1, 3-diphenylpropan-1-one (8a), White solid (85%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 7.2 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), (m, 4H), 7.22 (t, J = 7 Hz, 1H), 3.32 (t, J = 7.6 Hz, 2H), 3.09 (t, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.2, 141.3, 136.9, 133.1, 128.6, 128.6, 128.5, 128.1, 126.2, 40.5, Data are consistent with previously reported data. [D. W. Wang, K. Y. Zhao, C. Y. Xu, H. Y. Miao, Y. Q. Ding, ACS Catal. 2014, 4, ] Cl 3-(4-chlorophenyl)-1-phenylpropan-1-one (8b), pale yellow solid (71%). 1 H NMR (400 MHz, CDCl 3 ): δ (m, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.27 (s, 1H), 7.25 (s, 1H), (m, 2H), 3.28 (t, J = 7.6 Hz, 2H), 3.05 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.9, 139.7, 136.8, 133.2, 131.9, 129.8, (2C), 128.0, 40.1, Data are consistent with previously reported data. [D. W. Wang, K. Y. Zhao, C. Y. Xu, H. Y. Miao, Y. Q. Ding, ACS Catal. 2014, 4, ] 3
4 3-(4-methoxyphenyl)-1-phenylpropan-1-one (8c), colorless oil (95%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.96 (d, J = 7.2, 2H), 7.56 (t, J = 7.2 Hz, 1H), 7.45 (t, J = 7.4 Hz, 2H), 7.17 (d, J = 8.4 Hz, 2H), 6.84 (d, J = 8.8 Hz, 2H), 3.79 (s, 3H), 3.27 (t, J = 7.6 Hz, 2H), 3.02 (t, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.4, 158.0, 136.9, 133.3, 133.1, 129.4, 128.6, 128.1, 114.0, 55.3, 40.7, Data are consistent with previously reported data. [D. W. Wang, K. Y. Zhao, C. Y. Xu, H. Y. Miao, Y. Q. Ding, ACS Catal. 2014, 4, ] 1-phenyl-3-(p-tolyl)propan-1-one (8d), yellow oil (75%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 7.2 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.46 (t, J = 7.6 Hz, 2H), 7.16 (d, J = 8.4, 2H), 7.12 (d, J = 8.2, 2H), 3.29 (t, J = 7.8 Hz, 2H), 3.04 (t, J = 7.6 Hz, 2H), 2.33 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.4, 138.2, 136.9, 135.6, 133.1, 129.2, 128.6, 128.3, 128.1, 40.6, 29.7, Data are consistent with previously reported data. [S. Musa, L. Ackermann, D. Gelman, Adv. Synth. Catal. 2013, 355, ] 1-phenyl-3-(o-tolyl)propan-1-one (8e), white solid (74%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.98 (d, J = 7.2 Hz, 2H), 7.57 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), (m, 4H), 3.26 (t, J = 8 Hz, 2H), 3.06 (t, J = 7.8 Hz, 2H), 2.36 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.4, 139.4, 136.9, 136.0, 133.1, 130.4, 128.7, 128.6, 128.1, 126.3, 126.2, 39.1, 27.5, Data are consistent with previously reported data. [X. Liu, R. S. Ding, L. He, Y. M. Liu, Y. Cao, H. Y. He, K. N. Fan, ChemSusChem, 2013, 6, ] 3-([1,1'-biphenyl]-4-yl)-1-phenylpropan-1-one (8f), yellow solid (58%); 1 H Ph NMR (400 MHz, CDCl 3 ): δ 8.00 (d, J = 7.2 Hz, 2H), (m, 5H), (m, 4H), (m, 3H), 3.36 (t, J = 7.2 Hz, 2H), 3.13 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.2, 141.0, 140.4, 139.2, 136.9, 133.1, 128.9, 128.8, 128.6, 128.1, 127.3, 127.1, 127.0, 40.4, Data are consistent with previously reported data. [T. Kuwahara, T. Fukuyama, I. 4
5 Ryu, rg. Lett. 2012, 14, ] 3-(benzo[d][1,3]dioxol-5-yl)-1-phenylpropan-1-one (8g), colorless oil (58%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.95 (d, J = 8.4 Hz, 2H), 7.56 (t, J = 6.8, 1H), 7.46 (t, J = 6.8 Hz, 2H), (m, 3H), 5.92 (d, J = 1.2 Hz, 2H), 3.26 (t, J = 8.4 Hz, 2H), 3.00 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.2, 147.7, 145.9, 136.9, 135.1, 133.1, 128.6, 128.0, 121.2, 108.9, 108.3, 100.8, 40.7, Data are consistent with previously reported data. [X. J. Cui, Y. Zhang, F. Shi, Y. Q. Deng, Chem. Eur. J. 2011, 17, ] 3-(furan-2-yl)-1-phenylpropan-1-one (8h), yellow oil (94%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.98 (d, J = 7.2 Hz, 2H), 7.57 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.32 (d, J = 0.8 Hz, 1H), 6.29 (dd, J = 2.9, 2.0 Hz, 1H), 6.06 (d, J = 2.4 Hz, 1H), 3.34 (t, J = 7.6 Hz, 2H), 3.10 (t, J = 7.4 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.7, 154.8, 141.1, 136.8, 133.1, 128.6, 128.0, 110.3, 105.3, 36.9, Data are consistent with previously reported data. [D. W. Wang, K. Y. Zhao, C. Y. Xu, H. Y. Miao, Y. Q. Ding, ACS Catal. 2014, 4, ] S 1-phenyl-3-(thiophen-2-yl)propan-1-one (8i), yellow oil (75%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.97 (d, J = 7.6 Hz, 2H), 7.57 (t, J = 7.2 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.13 (dd, J =1.2, 2.6, 1H), (m, 1H), 6.87 (d, J = 2.8 Hz, 1H), (m, 2H), (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.6, 143.9, 136.8, 133.2, 128.7, 128.1, 126.9, 124.7, 123.4, 40.6, Data are consistent with previously reported data. [T. Kuwahara, T. Fukuyama, I. Ryu, rg. Lett. 2012, 14, ] 3-(naphthalen-2-yl)-1-phenylpropan-1-one (8j), white solid (86%); 1 H NMR (400 MHz, CDCl 3 ): δ 7.99 (d, J = 7.2 Hz, 2H), (m, 3H), 7.70 (s, 1H), 5
6 7.56 (t, J = 7.2 Hz, 1H), (m, 5H), 3.40 (t, J = 7.6 Hz, 2H), 3.25 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.2, 138.8, 136.9, 133.7, 133.1, 132.1, 128.6, , , 127.6, 127.5, 127.2, 126.5, 126.0, 125.3, 40.4, Data are consistent with previously reported data. [B. Q. Ding, Z. F. Zhang, Y. G. Liu, M. Sugiya, T. Imamoto, W. Zhang, rg. Lett. 2013, 14, ] 1-phenyl-1-(p-tolyl)propan-1-one (8k), white solid (76%); 1 H NMR (400 MHz, CDCl 3 ): δ 7.87 (d, J = 8.4 Hz, 2H), (m, 7H), 3.29 (t, J = 7.6 Hz, 2H), 3.07 (t, J = 7.8 Hz, 2H), 2.42 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.0, 144.0, 141.5, 134.5, 129.4, 128.6, 128.5, 128.3, 126.2, 40.5, 30.4, Data are consistent with previously reported data. [X. Liu, R. S. Ding, L. He, Y. M. Liu, Y. Cao, H. Y. He, K. N. Fan, ChemSusChem,2013, 6, ] 1-(4-chlorophenyl)-3-phenylpropan-1-one (8l), yellow solid (68%). 1 H NMR Cl (400 MHz, CDCl 3 ): δ 7.89 (d, J = 8.4 Hz, 2H), 7.43 (d, J = 8.4 Hz, 2H), (m, 5H), 3.27 (t, J = 7.8 Hz, 2H), 3.07 (t, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.0, 141.1, 139.2, 135.2, 129.5, 128.9, 128.6, 128.4, 128.2, 40.4, Data are consistent with previously reported data. [D. W. Wang, K. Y. Zhao, C. Y. Xu, H. Y. Miao, Y. Q. Ding, ACS Catal. 2014, 4, ] 1-(4-methoxyphenyl)-3-phenylpropan-1-one (8m), white solid (90%). 1 H NMR (400 MHz, CDCl 3 ): δ7.95 (d, J = 8 Hz, 2H), (m, 5H), 6.93 (d, J = 8.4 Hz, 2H), 3.87 (s, 3H), 3.26 (t, J = 7.8 Hz, 2H), 3.06 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 197.8, 163.5, 141.5, 130.3, 130.0, 128.5, 128.4, 126.1, 113.7, 55.5, 40.1, Data are consistent with previously reported data. [X. Liu, R. S. Ding, L. He, Y. M. Liu, Y. Cao, H. Y. He, K. N. Fan, ChemSusChem, 2013, 6, ] 6
7 1-(4-(methylthio)phenyl)-3-phenylpropan-1-one (8n), white solid (92%). 1 H S NMR (400 MHz, CDCl 3 ): δ 7.87 (d, J = 8.4 Hz, 2H), (m, 7H), 3.26 (t, J = 7.8 Hz, 2H), 3.06 (t, J = 7.8 Hz, 2H), 2.52 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.2, 145.8, 141.3, 133.2, , (2C), 126.2, 125.0, 40.3, 30.2, Data are consistent with previously reported data. [F. Caturla, J. M. Jiménez, N. Godessart, M. Amat, A. Cárdenas, L. Soca, J. Beleta, H. Ryder, M. Crespo, J. Med. Chem. 2004, 47, ] 1-(2,4-dimethylphenyl)-3-phenylpropan-1-one (8o), colorless oil (58%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.56 (s, 1H), (m, 5H), (m, 2H), 3.22 (t, J = 7.8 Hz, 2H), 3.04 (t, J = 7.6 Hz, 2H), 2.48 (s, 3H), 2.35 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ): δ 202.6, 141.9, 141.4, 138.7, 134.9, 132.9, 129.0, 128.5, 128.4, 126.3, 126.1, 42.9, 30.5, 21.5, Data are consistent with previously reported data. [Q. B. Jiang, T. L. Guo, Q. F. Wang, P. Wu, Z. K. Yu, Adv. Synth. Catal. 2013, 355, ] 1-(benzo[d][1,3]dioxol-5-yl)-3-phenylpropan-1-one (8p), white solid (87%). 1 H NMR (400 MHz, CDCl 3 ): δ 7.56 (dd, J = 8.2, 1.5 Hz, 1H), 7.45 (d, J = 1.6 Hz, 1H), (m, 5H), 6.83 (d, J = 8 Hz, 1H), 6.03 (s, 2H), 3.22 (t, J = 7.6 Hz, 2H), 3.05 (t, J = 7.6 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 197.3, 151.7, 148.2, 141.4, 131.8, 128.8, 128.5, 128.4, 126.1, 124.2, 107.9, 101.8, 40.2, Data are consistent with previously reported data. [P. Colbon, J. Ruan, M. Purdie, J. L. Xiao, rg. Lett. 2010, 12, ] 1-(naphthalen-2-yl)-3-phenylpropan-1-one (8q), White solid (93%). 1 H NMR (400 MHz, CDCl 3 ): δ 8.47 (s, 1H), 8.05 (d, J = 8.4 Hz, 1H), (m, 3H), (m, 2H), (m, 4H), 3.45 (t, J = 7.8 Hz, 2H), 3.14 (t, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 199.2, 141.4, 135.6, 134.2, 132.6, 129.7, 129.6, 128.6, (3C), 127.8, 126.8, 126.2, 123.9, 40.6, Data are consistent with previously reported data. [K. 7
8 Chakrabarti, B. Paul, M. Maji, B. C. Roy, S. Shee, S. Kundu, rg. Biomol. Chem, 2016, 14, ] 1-([1,1'-biphenyl]-4-yl)-3-phenylpropan-1-one (8r), white solid (66%); 1 H NMR (400 MHz, CDCl 3 ): δ 8.05 (d, J = 8.4 Hz, 2H), 7.69 (d, J = 8.4 Hz, 2H), 7.64 (d, J = 7.6 Hz, 2H), 7.48 (t, J = 7.6 Hz, 2H), 7.42 (d, J = 7.2 Hz, 1H), (m, 5H), 3.35 (t, J = 7.6 Hz, 2H), 3.12 (t, J = 7.8 Hz, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 198.8, 145.8, 141.4, 139.9, 135.6, 129.0, 128.7, 128.6, 128.5, 128.3, (2C signals), 126.2, 40.5, Data are consistent with previously reported data. [A. Zanardi, J A. Mata, E. Peris, J. Am. Chem. Soc. 2009, 131, ] 8
9 3. X-ray structures and data of 2 and 4 P1 Cl1 N1 C1 Ru1 N2 H1 RTEP of 2 with thermal ellipsoids at the 30% probability level. Hydrogen atoms have been omitted for clarity (CCDC No: ). 9
10 Table S2: Crystal data and structure refinement for 2 Identification code Complex 2 Empirical formula C 27 H 42 ClN 2 PRu Formula weight Temperature / K Crystal system Monoclinic Space group P2 1 /c a / Å, b / Å, c / Å (16), (15), (3) α/ o, β/ o, γ/ o 90.00, (13),90.00 Volume / Å (6) Z 4 ρ calc / mg mm μ / mm F (ooo) 1176 Crystal size / mm Ɵ range for data collection 6.2 to 52 o Index ranges -15 h 12, -12 k 13, -24 l 22 Reflections collected Independent reflections 5191[R(int) = (inf-0.9å)] Data/restraints/parameters 5191/0/300 Goodness-of-fit on F Final R indexes [I>2σ (I) i.e. F o > 4σ (F o )] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff.peak/hole/ e Å / Flack Parameters N Completeness
11 N1 P1 Ru1 N2 C1 H RTEP of 3 with thermal ellipsoids at the 30% probability level. Hydrogen atoms and C 6 H 6 have been omitted for clarity (CCDC No: ). Na 11
12 Table S3: Crystal data and structure refinement for 3 Identification code Complex 3 C 6 H 6 Empirical formula C 27 H 42 N 2 NaPRu C 6 H 6 Formula weight Temperature / K Wavelength 163(2)K A Crystal system Triclinic Space group P-1 a / Å, b / Å, c / Å (3),12.566(3),13.275(4) α/deg, β/deg, γ/deg (5),84.143(5),68.651(4) Volume / Å (7) Z 2 ρ calc / mg m μ / mm F (000) 660 Crystal size / mm Ɵ range for data collection 1.6 to deg Index ranges -13 h 11, -16 k 16, -17 l 11 Reflections collected Independent reflections Absorption correction Max. and min. transmission Refinement method 6939[R(int) = ] None and Full-matrix least-squares on F 2 Data/restraints/parameters 6939/0/349 Goodness-of-fit on F Final R indexes [I>2sigma(I)] R 1 = , wr 2 = Final R indexes [all data] R 1 = , wr 2 = Largest diff.peak/hole/ e Å /-0.65 Completeness
13 N Cl N
14 N Cl N
15 N N P i Pr 2 1
16 N N P i Pr 2 1
17 N P i Pr 2 1 N 17
18 N N P i Pr 2 Ru Cl H 2
19 N N P i Pr 2 Ru Cl H 2
20 54.69 N N H 2 Ru Cl P i Pr
21 N N P i Pr 2 Ru H Na 3
22 N N P i Pr 2 Ru H Na 3
23 N N Na 3 P i Pr 2 Ru H
24 N N P i Pr 2 Ru H 4 H
25 N N P i Pr 2 Ru H 4 H
26 79.13 N N H 4 Ru H P i Pr
27 a
28 a
29 Cl 8b
30 b Cl
31 c
32 c
33 d
34 d
35 e
36 e
37 f
38 f
39 g
40 g
41 h
42 h
43 S 8i PE
44 S 8i
45 j
46 j
47 k
48 k
49 Cl 8i
50 Cl 8i
51 m
52 m
53 S 8n
54 S 8n
55 o
56 o
57 p
58 p
59 q
60 q
61 r
62 r
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upporting Information huichi Yanagisawa, Tomoko udo, Ryoji Noyori, and Kenichiro Itami*,, Department of Chemistry and Research Center for Materials cience, Nagoya University, Nagoya 464-8602, Japan PRET,
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Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2009
Supporting Information Copyright Wiley-VC Verlag Gmb & Co. KGaA, 69451 Weinheim, 2009 A Stereodivergent Strategy to Both Product Enantiomers from the Same Enantiomer of a Stereoinducing Catalyst: Agelastatin
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