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-