Formation of Aryl-Carbon and Aryl-Heteroatom Bonds Using Copper(I)

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© Copyright by Rattan.K Gujadhur 2003 All Rights Reserved
Approved as to style and content by: The Formation of Aryl-Carbon and Aryl-Heteroatom Bonds Using Copper(I) Catalysts A Dissertation Presented By Rattan K. Gujadhur __________________________________________ D. Venkataraman, Chair __________________________________________ P. Lahti, Member __________________________________________ P.C. Uden, Member __________________________________________ M. Maroney, Member __________________________________________ J. Penelle, Member __________________________________ Bret Jackson, Department Head Chemistry Department of Chemistry
Page 1: Formation of Aryl-Carbon and Aryl-H
Page 5 and 6: ACKNOWLEDGEMENTS Completing a Ph.D.
Page 7 and 8: allows the development of protocols
Page 9 and 10: 3.1 Background 37 3.2 Introduction
Page 11 and 12: LIST OF TABLES Table 2.1: Bite angl
Page 13 and 14: LIST OF FIGURES Figure 2.1: X-Ray C
Page 15 and 16: LIST OF SCHEMES Scheme 1.1: Example
Page 17 and 18: LIST OF CHARTS Chart 1.1: Examples
Page 19 and 20: however, is limited to highly elect
Page 21 and 22: palladium complexes and simultaneou
Page 23 and 24: HO X Evindar, G.; Batey, R. A. Org.
Page 25 and 26: R= HO X H 2N Br R4 R4 X OMe COOCH3
Page 27 and 28: 1.4 Organization of this dissertati
Page 29 and 30: (9) Beller, M. "Palladium-Catalyzed
Page 31 and 32: Oxidation States of Copper in an Ul
Page 33 and 34: neocuproine, and diimines 5 and 2,2
Page 35 and 36: Table 2.1: Bite Angles and Cu-P Bon
Page 37 and 38: Figure 2.3: X-Ray Crystal Structure
Page 39 and 40: Figure 2.5: X-Ray Crystal Structure
Page 41 and 42: N N Cu NO Ph3P PPh 3 3 8 N N Chloro
Page 43 and 44: The complex [Cu(CH3CN)4]PF6 was mad
Page 45 and 46: Figure 2.13: X-Ray Crystal Structur
Page 47 and 48: provides us with the opportunity to
Page 49 and 50: 2.15). Morever, such an unexpected
Page 51 and 52: Mononuclear complexes such as [Cu(P
Page 53 and 54:
Triphenylphosphine with Copper(I) H
Page 55 and 56:
Br Br Bu t + + OH ONa OMe 5 mol% Pd
Page 57 and 58:
3.3 Optimization and Results with t
Page 59 and 60:
were observed, when 1 was used in s
Page 61 and 62:
in almost quantitative yield in 36
Page 63 and 64:
also shown that electron-deficient
Page 65 and 66:
(15) Gujadhur, R. K.; Bates, C. G.;
Page 67 and 68:
copper catalysts may provide an alt
Page 69 and 70:
and 7 have lower yields possibly be
Page 71 and 72:
Figure 4.1: X-Ray Crystal Structure
Page 73 and 74:
Recently, Goodbrand and Hu reported
Page 75 and 76:
We proposed to take aliquots of the
Page 77 and 78:
In our optimization experiments we
Page 79 and 80:
obtained by current Hartwig-Buchwal
Page 81 and 82:
Involvement of Bis(Phosphine)Pallad
Page 83 and 84:
E. "Photostudies of [Cu(bipy)(PPh3)
Page 85 and 86:
strategies, such as, Phase Transfer
Page 87 and 88:
Table 5.1: Reactions of Substituted
Page 89 and 90:
5.4 Existing Methods for the Synthe
Page 91 and 92:
formation of aryl-selenium bonds, w
Page 93 and 94:
Table 5.5: Reaction of electron-ric
Page 95 and 96:
5.7 References (1) Craig Bates disc
Page 97 and 98:
(15) El-Bayoumy, K. "Overview: The
Page 99 and 100:
(31) Liotta, D., Ed. Organoselenium
Page 101 and 102:
(50) Van Bierbeek, A.; Gingras, M.
Page 103 and 104:
Substitution of the complexes [Cu(P
Page 105 and 106:
6.1 Future Work The discovery of ne
Page 107 and 108:
6.2 References (1) Bates, C. G.; Sa
Page 109 and 110:
Copper(I) Phosphine Complexes Synth
Page 111 and 112:
Synthesis of nitrato bis(triphenylp
Page 113 and 114:
ethanol and ether, and crystallized
Page 115 and 116:
orange-yellow solid. Recrystallizat
Page 117 and 118:
Compound (see Chapter 2) Formula Fo
Page 119 and 120:
in the Cambridge Structural Databas
Page 121 and 122:
mmol) and Na2CO3 (1.13 g, 9.7 mmol)
Page 123 and 124:
as the internal reference. Elementa
Page 125 and 126:
130.7 (C3’, C3a’), 125.7 (C3, C
Page 127 and 128:
Ha’), 7.32-7.14 (m, 3H; Hd, He, H
Page 129 and 130:
Purification by flash chromatograph
Page 131 and 132:
7.16-6.96 (m, 4H; Hf, Hb, Hb’, He
Page 133 and 134:
NC H a' H a H d' H dH c H H O 1-Met
Page 135 and 136:
GC Correction factors used for calc
Page 137 and 138:
are indicated as s, singlet; d, dou
Page 139 and 140:
emoved under reduced pressure and t
Page 141 and 142:
. H 2 H 3 H 1 H 4 H 5 H 11 R H H12
Page 143 and 144:
1-[4-(diphenylamino)phenyl]ethanone
Page 145 and 146:
Methyl 4-(diphenylamino)benzoate (e
Page 147 and 148:
H 2 H 3 R H 1 H4 R R N R R=COOCH 3
Page 149 and 150:
H 6 N H 5 H 4 H 3 H 1 O O O O H 2 1
Page 151 and 152:
H 3 H 2 H 1 N Triphenylamine (entry
Page 153 and 154:
2-Methyl-N, N-diphenylaniline (entr
Page 155 and 156:
(5.0 mL) were injected into the tub
Page 157 and 158:
H c H b H d H a e CH3 S CH 3 H f Hh
Page 159 and 160:
n-Butyl 4-Iodophenyl Sulfide (entry
Page 161 and 162:
1H; Hd), 7.75-7.73 (d, 1H; He), 7.6
Page 163 and 164:
General Method for the Formation of
Page 165 and 166:
Phenyl-p-tolyl-selenide (entry 2, T
Page 167 and 168:
(C9, C13), 128.13 (C10, C12), 128.0
Page 169 and 170:
H f H e Hd Ha' Hb' S Se S Se H a H
Page 171 and 172:
2-aniline-phenyl-phenyl selenide (e
Page 173 and 174:
Hc’), 3.88 (s, 3H; methyl protons
Page 175 and 176:
Hc’). 13 C NMR (75 MHz, CDCl3) δ
Page 177 and 178:
Barron, P. F.; Cyason, J. C.; Healy
Page 179 and 180:
D` Aprano, G.; Leclerc, M.; Zotti,
Page 181 and 182:
Herradura, P. S.; Pendola, K. A.; G
Page 183 and 184:
Louie, J.; Hartwig, J. F. "Transmet
Page 185 and 186:
Procter, D. J. "The Synthesis of Th
Page 187:
Wolfe, J. P.; Wagaw, S.; Marcoux, J
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Formation of Aryl-Carbon and Aryl-Heteroatom Bonds Using Copper(I)

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