chapter 2 palladium catalysts in suzuki cross- coupling reaction

More documents

Recommendations

Info

2-Acetylbiphenyl: 1 H NMR (400 MHz, CDCl3) δ: 7.57-7.49 (m, 4H); 7.45-7.38 (m, 3H); 7.37-7.33 (m, 2H); 2.01-1.99 (s, 3H); 13 C NMR (100 MHz, CDCl3) δ: 205.0, 141.2, 140.9, 140.8, 130.9, 130.5, 129.1, 128.9, 128.1, 127.7, 30.6; MS: 196 (M + ), 181, 152. 4-Methylbiphenyl: 1 H NMR (400 MHz, CDCl3) δ: 7.67-7.26 (m, 9H); 2.49- 2.41 (m, 3H); 13 C NMR (100 MHz, CDCl3) δ: 141.5, 138.7, 137.3, 129.8, 129.0, 127.3, 127.3, 21.4; MS: 168 (M + ), 152. 4-Phenylaniline: 1 H NMR (400 MHz, CDCl3) δ: 7.62-7.59 (d, 2H); 7.49-7.44 (m, 4H); 7.35-7.31 (m, 1H); 6.79-6.77 (m, 2H); 3.71 (s, 2H); 13 C NMR (100 MHz, CDCl3) δ: 146.2, 141.5, 131.8, 128.9, 128.3, 126.7, 126.5, 115.7; MS: 169 (M + ). 50
51 Table 4.1. Purification of coupling products by column chromatography. Product Gradient Elution Melting Point (°C) Appearance Purity % 4-Acetylbiphenyl Hexane/ethyl acetate (12:1) 119.2-121.2 white >99 4-Methylbiphenyl Hexane/ethyl acetate (12:1) 45.5-47.4 colorless >99 4-Methoxybiphenyl Hexane/ethyl acetate (16:1) 85.8-88.4 white >99 4-Nitrobiphenyl Hexane/CH2Cl2 (9:3) 112.6-115.1 yellow 99 4-Cyanobiphenyl Hexane/CH2Cl2 (9:3) 86.4-88.8 white >99 1-Phenylnaphthalane Hexane/ethyl acetate (16:1) oily colorless 99 2-Phenylnaphthalane Hexane/ethyl acetate (15:1) 101-102.1 white >99 3-Acetylbiphenyl Hexane/ethyl acetate (14:1) oily yellow >99 2-Methoxybiphenyl Hexane/ethyl acetate (14:1) oily colorless >99 3-Methoxybiphenyl Hexane/ethyl acetate (16:1) oily light yellow 98 4-Phenylbenzaldehyde Hexane/ethyl acetate (13:1) 59.6-61.3 white >99 2-Methylbiphenyl Hexane/ethyl acetate (17:1) oily colorless 99 3-Phenylpyridine Hexane/ethyl acetate (7:1) oily light yellow 97 2-Acetylbiphenyl Hexane/ethyl acetate (12:1) oily light yellow 98 4-Phenylaniline Hexane/ethyl acetate (1:4) 52.6-55.9 orange 98 1
Page 1 and 2:
SHORT-TIME SUZUKI REACTIONS OF ARYL
Page 3 and 4:
ACKNOWLEDGEMENTS Firstly, I’d lik
Page 5 and 6:
ÖZET ARİL HALOJENÜRLERİN HAVA A
Page 7 and 8:
3.2.2. Catalysts Anchored to Inorga
Page 9 and 10:
LIST OF FIGURES Figure Page Figure
Page 11 and 12: Figure A.27. 13 C NMR of 4-cyanobip
Page 13 and 14: CHAPTER 1 INTRODUCTION The palladiu
Page 15 and 16: CHAPTER 2 PALLADIUM CATALYSTS IN SU
Page 17 and 18: 2.1.2. The Coordination Geometry of
Page 19 and 20: R 1 R 1 4. Sonogashira Reaction: H
Page 21 and 22: 2.2.1. Mechanism of Suzuki Coupling
Page 23 and 24: As a result, organic group or hydri
Page 25 and 26: 2.2.2.2. Halogen Effect Nearly all
Page 27 and 28: found to be excellent complexes for
Page 29 and 30: R Table 2.2. Examples from literatu
Page 31 and 32: L R Pd X R Pd L OR'' X L L + OR' R'
Page 33 and 34: omides and iodides is performed eff
Page 35 and 36: times for the transformation of a l
Page 37 and 38: R Br + (HO) 2B R' 5% Pd(OAc) 2 15%
Page 39 and 40: of insoluble solids are among the m
Page 41 and 42: could be reused multiple times. The
Page 43 and 44: 3.2.2. Catalysts Anchored to Inorga
Page 45 and 46: SO 2NH N Pd SO 2 N SO 2 NH NH H O1.
Page 47 and 48: utilized them in Heck and Suzuki co
Page 49 and 50: Smith et al introduced the use of P
Page 51 and 52: • Complexes immobilized in zeolit
Page 53 and 54: 3.3.3. Preparation of Zeolite-Suppo
Page 55 and 56: CHAPTER 4 EXPERIMENTAL STUDY 4.1. P
Page 57 and 58: temperature, the catalyst was recov
Page 59 and 60: amount of both reactant and product
Page 61: 4-Methoxybiphenyl: 1 H NMR (400 MHz
Page 65 and 66: CHAPTER 5 RESULTS AND DISCUSSIONS I
Page 67 and 68: Table 5.2. The effect of base on Pd
Page 69 and 70: Table 5.4. The Optimization of Pd-N
Page 71 and 72: H 3COC Table 5.5. Effect of zeolite
Page 73 and 74: Table 5.6. Pd(NH3)4 2+ -loaded NaY
Page 75 and 76: The type of other organic co-solven
Page 77 and 78: yield was very low (Table 5.8, entr
Page 79 and 80: evealed excellent reactivity toward
Page 81 and 82: CHAPTER 6 CONCLUSIONS In this thesi
Page 83 and 84: REFERENCES Albisson, D.A., Bedford,
Page 85 and 86: Choudary, B.M., Madhi, S., Chowdari
Page 87 and 88: Heiden, M. Plenio, H. 2004. ‘‘H
Page 89 and 90: Coupling Reactions of Aryl Chloride
Page 91 and 92: Phan, N.T.S., Brown, D.H., Styring,
Page 93 and 94: Wolfe, J.P., Singer, R.A., Yang, B.
Page 95 and 96: Figure A.1. 13 C NMR of 1-phenylnap
Page 97 and 98: Figure A.3. 13 C NMR of 2-acetylbip
Page 99 and 100: Figure A.5 . 13 C NMR of 2-methoxyb
Page 101 and 102: Figure A.7. 13 C NMR of 2-methylbip
Page 103 and 104: Figure A.9. 13 C NMR of 2-phenylnap
Page 105 and 106: Figure A.11. 13 C NMR of 3-acetylbi
Page 107 and 108: Figure A.13. 13 C NMR of 3-methoxyb
Page 109 and 110: Figure A.15. 13 C NMR of 3-phenylpy
Page 111 and 112: Figure A.17. 13 C NMR of 4-acetyl-4
Page 113 and 114:
Figure A.19. 13 C NMR of 4-methoxyb
Page 115 and 116:
Figure A.21. 13 C NMR of 4-methylbi
Page 117 and 118:
Figure A.23. 13 C NMR of 4-phenylbe
Page 119 and 120:
Figure A.25. 13 C NMR of 4-acetylbi
Page 121 and 122:
Figure A.27. 13 C NMR of 4-cyanobip
Page 123 and 124:
Figure A.29. 13 C NMR of 4-nitrobip
Page 125 and 126:
Figure A.31. 13 C NMR of 4-phenylan
Page 127 and 128:
APPENDIX B MASS SPECTRUMS OF SUZUKI
Page 129 and 130:
Figure B.2. Mass spectrum of 2-acet
Page 131 and 132:
Figure B.4. Mass spectrum of 2-meth
Page 133 and 134:
Figure B.6. Mass spectrum of 3-acet
Page 135 and 136:
Figure B.8. Mass spectrum of 3-phen
Page 137 and 138:
Figure B.10. Mass spectrum of 4-phe
Page 139 and 140:
Figure B.12. Mass spectrum of 4-met
Page 141 and 142:
Figure B.14. Mass spectrum of 4-cya
Page 143:
Figure B.16. Mass spectrum of 4-met
show all

chapter 2 palladium catalysts in suzuki cross- coupling reaction

You also want an ePaper? Increase the reach of your titles

Delete template?

Save as template?