chapter 2 palladium catalysts in suzuki cross- coupling reaction

More documents

Recommendations

Info

H H PCy 2 Me2N 1 2 3 Fe O P 4 Cl t-Bu t-Bu PCy 2 Pd CH 3 N OH 2 Fe Fe P(t-Bu) 2 Fe 7 8 CH 3 N Pd Cl PCy 3 CH 3 PCy 2 Fe S Pd 2 Me tBu 10 11 12 Me N N I I Pd 13 N N Me R O O PCy 2 PCy 2 PCy 2 Fe 5 6 Ar N Cl - N 9 Ar O O Ar = 2,4,6-(Me) 3C 6H 2 Figure 2.10. Different types of ligands and palladium complexes used in Suzuki reactions 14 P'Bu 2 H Cl N Pd Cl PCy 3 16
R Table 2.2. Examples from literature on Suzuki reactions of aryl chlorides Cl + B(OH) 2 R' Pd / ligand R R' Entry R Catalyst/ligand Reaction Conditions Yield Ref. 1 4-CHO, 3-CHO, 2-CHO, 3-MeCO 2 4-COMe, 4-Me, 2-Me, 4-OMe, PdCl2(PCy3)2 CsF, NMP, 100 °C 83-98 Shen 1997 [Pd2(dba)3]/ P(t-Bu)3 Cs2CO3, dioxane, 80-90 °C 82-92 Littke and Fu 1998 3 4-OMe Pd(OAc)2/ 1 CsF, dioxane, RT 92 Old et al. 1998 4 -NO2, CN, CO2Me, 2-COMe 5 4-H, OMe, 2-OMe 6 4-COMe, CN, NO2 Pd(OAc)2/ 2, 3 KF, THF, RT 88-98 Wolfe and Buchwald 1999 [Pd(dba)3]/ 4 CsF/ Cs2CO3, dioxane, 100 °C 83-99 Li 2001 9 K3PO4, DMF,130 °C 90-95 Zim et al. 2000 7 4-COMe 10 Met. A: K2CO3, TBAB, water, 100 °C Met. B: KOH , TBAB methanol/ water (3:1), RT Botella and Najera 2002 8 4-NO2, COMe 11, 12 Cs2CO3, dioxane, Gong et al. 100 ° C 2005 9 4-COMe 13 K2CO3, toluene, 120 °C 60 Hermann 1998 10 4-CO2Me, Me, [Pd(dba)3]/ 14 Cs2CO3, dioxane, 80 °C 88-99 Zhang et OCH3 al. 1999 Since the discovery of stable N-heterocyclic carbene (NHC) by Arduengo et al. (Arduengo et al. 1992), N-heterocyclic carbene complexes (NHCs) have become 17
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: found to be excellent complexes for
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 and 62: 4-Methoxybiphenyl: 1 H NMR (400 MHz
Page 63 and 64: 51 Table 4.1. Purification of coupl
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

Create successful ePaper yourself

Delete template?

Save as template?