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Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is © The Royal Society of Chemistry 2014 Supplementary Material Nickel-Catalyzed Substitution Reactions of Propargyl Halides with Organotitanium Reagents Qing-Han Li,a,b,* Jung-Wei Liao,a Yi-Ling Huang,a Ruei-Tang Chianga and Han-Mou Gaua,* a Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan b College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041, China e-mail: [email protected] - S1- Table of Contents I. 1H and 13C NMR Spectra of Aryltitanium Reagents S3 1. (2-MeOC6H4)Ti(O-i-Pr)3 (4e) S3 2. (2,6-Me2C6H3)Ti(O-i-Pr)3 (4j) S5 II. 1H and 13C NMR Spectra of Coupling Products S7 1. 1-Phenyl-1,2-propadiene (2aa) S7 2. 1-(4-Methylphenyl)-1,2-propadiene (2ab) S9 3. 1-(2-Methylphenyl)-1,2-propadiene (2ac) S11 4. 1-(4-Methoxyphenyl)-1,2-propadiene (2ad) S13 5. 1-(2-Methoxyphenyl)-1,2-propadiene (2ae) S15 6. 1-(3,5-Dimethylphenyl)-1,2-propadiene (2af) S17 7. 1-(2-Naphthyl)-1,2-propadiene (2ag) S19 8. 1-(4-Trifluoromethylphenyl)-1,2-propadiene (2ah) S21 9. 1-cyclohexyl-1,2-propadiene (2ai) S23 10. 1-(2,6-Dimethylphenyl)-1,2-propadiene (2aj) S25 11. 1-(2,6-Dimethylphenyl)-4-(bromomethyl)-1,2,4-pentatriene (2aj’) S27 12. 3-Phenyl-1,2-pentadiene (2ba) S29 13. 3-(2-Methylphenyl)-1,2-pentadiene (2bc) S31 14. 3-(3,5-Dimethylphenyl)-1,2-pentadiene (2bf) S33 15. 3-(2,6-Dimethylphenyl)-1,2-pentadiene (2bj) S35 16. 3-Phenyl-1,2-butadiene (2ca) S37 17. 3-(2-Methylphenyl)-1,2-butadiene (2cc) S39 18. 1-Phenyl-1,2-butadiene (2da) S41 19. 1-(2-Methylphenyl)-1,2-butadiene (2dc) S43 20. 3-Phenyl-1,2-octadiene (2ea) S45 21. 1-Phenyl-2-octyne (3ea) S47 22. 1-(2-Methylphenyl)-2-octyne (3ec) S49 23. 1-(3,5-Dimethylphenyl)-2-octyne (3ef) S51 24. 3-(2,6-Dimethylphenyl)-1,2-octadiene (2ej) S53 25. 1-(2,6-Dimethyl)-2-octyne (3ej) S55 26. 1,3-Diphenylpropyne (3fa) S57 27. 1-Phenyl-3-(2-methylphenyl)propyne (3fc) S59 28. 1-Phenyl-2-octyne (3ga) S61 - S2- I. 1H and 13C NMR Spectra of Aryltitanium Reagents 1 H NMR Spectrum of (2-MeOC6H4)Ti(O-i-Pr)3 (4e) OMe Ti(O-i-Pr)3 4e - S3- 13 C NMR Spectrum of (2-MeOC6H4)Ti(O-i-Pr)3 (4e) OMe Ti(O-i-Pr)3 4e - S4- 1 H NMR Spectrum of (2,6-Me2C6H3)Ti(O-i-Pr)3 (4j) Ti(O-i-Pr)3 4j - S5- 13 C NMR Spectrum of (2,6-Me2C6H3)Ti(O-i-Pr)3 (4j) Ti(O-i-Pr)3 4j - S6- II. 1H and 13 C NMR Spectra of Coupling Products II.1. 1H NMR Spectrum of 1-Phenyl-1,2-propadiene (2aa) 2aa - S7- 13C NMR Spectrum of 1-Phenyl-1,2-propadiene (2aa) 2aa - S8- II.2. 1H NMR Spectrum of 1-(4-Methylphenyl)-1,2-propadiene (2ab) Me 2ab - S9- 13C NMR Spectrum of 1-(4-Methylphenyl)-1,2-propadiene (2ab) Me 2ab - S10- II.3. 1H NMR Spectrum of 1-(2-Methylphenyl)-1,2-propadiene (2ac) Me 2ac - S11- 13C NMR Spectrum of 1-(2-Methylphenyl)-1,2-propadiene (2ac) Me 2ac - S12- II.4. 1H NMR Spectrum of 1-(4-Methoxyphenyl)-1,2-propadiene (2ad) MeO 2ad - S13- 13C NMR Spectrum of 1-(4-Methoxyphenyl)-1,2-propadiene (2ad) MeO 2ad - S14- II.5. 1H NMR Spectrum of 1-(2-Methoxyphenyl)-1,2-propadiene (2ae) MeO 2ae - S15- 13C NMR Spectrum of 1-(2-Methoxyphenyl)-1,2-propadiene (2ae) MeO 2ae - S16- II. 6. 1H NMR Spectrum of 1-(3,5-Dimethylphenyl)-1,2-propadiene (2af) Me Me 2af - S17- 13C NMR Spectrum of 1-(3,5-Dimethylphenyl)-1,2-propadiene (2af) Me Me 2af - S18- II.7. 1H NMR Spectrum of 1-(2-Naphthyl)-1,2-propadiene (2ag) 2ag - S19- 13C NMR Spectrum of 1-(2-Naphthyl)-1,2-propadiene (2ag) 2ag - S20- II. 8. 1H NMR Spectrum of 1-(4-Trifluoromethylphenyl)-1,2-propadiene (2ah) F3C 2ah - S21- 13C NMR Spectrum of 1-(4-Trifluoromethylphenyl)-1,2-propadiene (2ah) F3C 2ah - S22- II.9. 1H NMR Spectrum of (1,2-Propadienyl)-cyclohexane (2ai) 2ai - S23- 13C NMR Spectrum of 1-cyclohexyl-1,2-propadiene (2ai) 2ai - S24- II.10. 1H NMR Spectrum of 1-(2,6-Dimethylphenyl)-1,2-propadiene (2aj) Me Me 2aj - S25- 13C NMR Spectrum of 1-(2,6-Dimethylphenyl)-1,2-propadiene (2aj) Me Me 2aj - S26- II.11. 1H NMR Spectrum of 1-(2,6-Dimethylphenyl)-4-(bromomethyl)-1,2,4-pentatriene (2aj’) Me Me Br 2aj' - S27- 13C NMR Spectrum of 1-(2,6-Dimethylphenyl)-4-(bromomethyl)-1,2,4-pentatriene (2aj’) Me Me Br 2aj' - S28- II.12. 1H NMR Spectrum of 3-Phenyl-1,2-pentadiene (2ba) Et 2ba - S29- 13C NMR Spectrum of 3-Phenyl-1,2-pentadiene (2ba) Et 2ba - S30- II.13. 1H NMR Spectrum of 3-(2-Methylphenyl)-1,2-pentadiene (2bc) Et Me 2bc - S31- 13C NMR Spectrum of 3-(2-Methylphenyl)-1,2-pentadiene (2bc) Et Me 2bc - S32- II.14. 1H NMR Spectrum of 3-(3,5-Dimethylphenyl)-1,2-pentadiene (2bf) Et Me Me 2bf - S33- 13C NMR Spectrum of 3-(3,5-Dimethylphenyl)-1,2-pentadiene (2bf) Et Me Me 2bf - S34- II.15. 1H NMR Spectrum of 3-(2,6-Dimethylphenyl)-1,2-pentadiene (2bj) Et Me Me 2bj - S35- 13C NMR Spectrum of 3-(2,6-Dimethylphenyl)-1,2-pentadiene (2bj) Et Me Me 2bj - S36- II.16. 1H NMR Spectrum of 3-Phenyl-1,2-butadiene (2ca) Me 2ca - S37- 13C NMR Spectrum of 3-Phenyl-1,2-butadiene (2ca) Me 2ca - S38- II.17. 1H NMR Spectrum of 3-(2-Methylphenyl)-1,2-butadiene (2cc) Me Me 2cc - S39- 13C NMR Spectrum of 3-(2-Methylphenyl)-1,2-butadiene (2cc) Me Me 2cc - S40- II.18. 1H NMR Spectrum of 1-Phenyl-1,2-butadiene (2da) Me 2da - S41- 13C NMR Spectrum of 1-Phenyl-1,2-butadiene (2da) Me 2da - S42- II.19. 1H NMR Spectrum of 1-(2-Methylphenyl)-1,2-butadiene (2dc) Me Me 2dc - S43- 13C NMR Spectrum of (1,2-Butadienyl)-2-methyl-benzene (2dc) Me Me 2dc - S44- II.20. 1H NMR Spectrum of 3-Phenyl-1,2-octadiene (2ea) 2ea - S45- 13C NMR Spectrum of 3-Phenyl-1,2-octadiene (2ea) 2ea - S46- II.21. 1H NMR Spectrum of 1-Phenyl-2-octyne (3ea) 3ea - S47- 13C NMR Spectrum of 2-octynylbenzene (3ea) 3ea - S48- II.22. 1H NMR Spectrum of 1-(2-Methylphenyl)-2-octyne (3ec) Me 3ec - S49- 13C NMR Spectrum of 1-(2-Methylphenyl)-2-octyne (3ec) Me 3ec - S50- II.23. 1H NMR Spectrum of 1-(3,5-Dimethylphenyl)-2-octyne (3ef) Me 3ef Me - S51- 13C NMR Spectrum of 1-(3,5-Dimethylphenyl)-2-octyne (3ef) Me 3ef Me - S52- II.24. 1H NMR Spectrum of 3-(2,6-Dimethylphenyl)-1,2-octadiene (2ej) Me Me 2ej - S53- 13C NMR Spectrum of 3-(2,6-Dimethyl)-1,2-octadiene (2ej) Me Me 2ej - S54- II.25. 1H NMR Spectrum of 1-(2,6-Dimethyl)-2-octyne (3ej) Me Me 3ej - S55- 13C NMR Spectrum of 1-(2,6-Dimethyl)-2-octyne (3ej) Me Me 3ej - S56- II.26. 1H NMR Spectrum of 1,3-Diphenylpropyne (3fa) 3fa - S57- 13C NMR Spectrum of 1,3-Diphenylpropyne (3fa) 3fa - S58- II.27. 1H NMR Spectrum of 1-Phenyl-3-(2-methylphenyl)propyne (3fc) Me 3fc - S59- 13C NMR Spectrum of 1-Phenyl-3-(2-methylphenyl)propyne (3fc) Me 3fc - S60- 1H NMR Spectrum of 1-Phenyl-2-octyne (3ga) 3ga - S61- 13C NMR Spectrum of 1-Phenyl-2-octyne (3ag) 3ga - S62-.

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