Reagents for Direct Functionalization of C-H

A concise and informative collection of articles on the synthesis of organic, biological and medicinal materials. Key Features: Detailed information on 200 reagents to be used for the functionalization of C-H bonds in the carbon backbone of organic molecules A systematic approach to the use of organometallic compounds in organic synthesis Articles will stress chemical aspects such as yield, conversion, specifity [enantio, stereo, regio, chemo], and where applicable, catalyst loading/turnover

Professor Philip L. Fuchs, Department of Chemistry, Purdue University, IN
He began his career at Purdue in 1973. Since that time, he has graduated an extended family of 55 Ph.D.s. His awards and honors include an Eli Lilly young faculty fellowship (1975), an Alfred P. Sloan fellowship (1977), a Pioneer in Laboratory Robotics award (1986), a Martin teaching award (1991), and being voted by the students as one of Top 10 Teachers in School of Science at Purdue (1991, 1993, 1995, 1996).
Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the Electronic Encyclopedia of Organic Reagents (e-EROS), an online dynamic encyclopedia published by John Wiley & Sons.

Preface

ix

Introduction

1

(8)

Recent Review Articles and Monographs

9

(2)

Allyl Triflone

11

(1)

2-Amino-3-Picoline

12

(5)

1,2-Benziodoxoyl-3(1H)-one Derivatives

17

(3)

2,2-Bis{[2-[4(S)-tert-butyl-1,3-oxazinyl]} propane

20

(6)

Bis(cyclopentadienyl)methylzirconium Tetraphenylborate-Tetrahydrofuran

26

(2)

Bis[dimethyl(μ-dimethyl sulfide)-platinum(II)]

28

(2)

N-Bromosuccinimide

30

(11)

Carbon Tetrabromide

41

(2)

Carbon Tetraiodide

43

(2)

4-(4-Chlorophenyl)-3-hydroxy-2(3H) thiazolethione

45

(3)

Chromium(VI) Oxide

48

(5)

Chromium(VI) Oxide-3,5-Dimethylpyrazole

53

(1)

Chromium(VI) Oxide-Dipyridine

54

(3)

Chromyl Acetate

57

(3)

Copper(I){Hydrotris(3,4,5-tribromo)pyrazolylborate}(acetonitrile)

60

(3)

Copper(I),[Hydrotris[3-(2,4,6-trimethylphenyl)-1H-pyrazolato-N1] borato(1-)-N2, N2N2

63

(1)

Copper(II) Acetate

64

(7)

Copper(II) Chloride

71

(8)

Di-(-)-(1R,2S)-2-phenyl-1-cyclohexyl Diazenedicarboxylate

79

(1)

(Diacetoxyiodo)benzene

80

(9)

Dibenzoyl Peroxide

89

(10)

Di-t-butyl Chromate

99

(3)

Di-t-butyl Peroxide

102

(5)

Dimethyl Diazomalonate

107

(6)

Dimethyldioxirane

113

(6)

Dipotassium Tetrachloroplatinate(II)

119

(1)

Dirhodium(II) bis-{1,3-[N,N'-di(4-Dodecyl-Benzenesulfonyl)-(2S,2'S),(5R,5'R)-5,5'-Prolinate]Benzene}

120

(2)

Dirhodium(II) Tetra(caprolactamate)

122

(2)

Dirhodium(II) Tetrakis(perfluorobutyrate)

124

(2)

Dirhodium(II) Tetrakis(trifluoroacetate)

126

(3)

Dirhodium(II) Tetrakis(triphenylacetate)

129

(3)

Dirhodium(II) Tetraacetamide

132

(2)

Dirhodium(II) Tetraacetate

134

(10)

Dirhodium(II) Tetrakis[Alkyl 2-oxaazetidine-4(S)-carboxylate]

144

(2)

Dirhodium(II) Tetrakis[1-[[(4-dodecylphenyl]sulfonyl]-prolinate]

146

(8)

Dirhodium(II) Tetrakis[methyl 1-(3-phenylpropanoyl)-2-oxaimidazolinidinecarboxylate]

154

(3)

Dirhodium(II) Tetrakis[methyl 2-oxapyrrolidine-carboxylate]

157

(3)

Dirhodium(II) Tetrakis[methyl 2-oxooxazolidine-4(S)-carboxylate]

160

(2)

Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]

162

(4)

Dirhodium(II) Tetraoctanoate

166

(3)

Disodium Tetrachloroplatinate(II)

169

(2)

Ethyl Azidoformate

171

(10)

Gallium Trichloride

181

(6)

1-Hydroxy-1,2-benziodoxol-3(1H)-one

187

(3)

Hypofluorous Acid

190

(1)

Hypofluorous Acid, Acetonitrile Complex

191

(6)

Iridium(V) Pentahydrobis(isopropylphosphine)

197

(1)

Iron(II) Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2)

198

(4)

Iron(II) Perchlorate

202

(1)

Iron(II) Phthalocyanine

202

(2)

Iron(II) 1,3,2-Benzodioxaborol-2-yldicarbonyl(η5-2,4-cyclopentadien-1-yl)

204

(3)

Mercury(0)

207

(2)

Methyl Phenyldiazoacetate

209

(5)

Methyl(trifluoromethyl)dioxirane

214

(7)

Oxaziridine, 3-Fluoro-3-(heptafluoropropyl)-2-(nonafluorobutyl)

221

(8)

Palladium(II) Acetate

229

(24)

Pinacol Diborane

253

(7)

Pinacolborane

260

(3)

Platinum(II) Chloride

263

(8)

Rhenium(VII) Methyltrioxo

271

(5)

Rhenium(VII) Aquamethyloxodiperoxy

276

(7)

Rhenium(VII) Methyloxodiperoxy

283

(4)

Rhodium(I) bis Cyclooctene Chloride Dimer

287

(6)

Rhodium(I) Carbonyl(chloro)bis(triphenylphosphine)

293

(10)

Rhodium(I) Chlorotris(triphenylphosphine)

303

(12)

Ruthenium(0) Dodecacarbonyl, Triangulo

315

(3)

Ruthenium(II) Dichlorotris(triphenylphosphine)

318

(4)

Ruthenium(II), bis[N,N-bis-[(2-pyridyl-kN)methyl]-2-pyridinemethanamine-N1,N2] di-μ-chloride

322

(2)

Ruthenium(III) Chloride

324

(4)

Ruthenium(III) N,N',N'',-Trimethyl-1,4,7-triazacyclononane + Ruthenium(II) cis-diaquabis(6,6'-dichloro-2,2'-bipyridine)bistriflate

328

(3)

Ruthenium(VIII) Oxide

331

(10)

Selenium(IV) Oxide

341

(2)

Silver(I) [tris[3,5-bis(trifluoromethyl)-1H-pyrazolato-N1]hydroborato(1-)-N2,N2',N2''']-tetrahydrofuran

343

(4)

Triethylborane

347

(15)

Trifluoromethyl Sulfonyl Ethynyl Benzene

362

(1)

Triisopropylsilylethynyl Triflone

363

(1)

Tungsten(II) Tricarbonyl(4,6-dimethyl-1,3,2-benzodioxaborol-2-yl)[(1,2,3,4,5,-η)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl)

364

(2)

Tungstoboric Acid, Tetrakis(tetrabutylammonium) Salt

366

(5)

Vanadium(VI) Dioxobis(pyrazine-2-carboxylate) Tetrabutylammonium

371

(4)

Vanadium(V) Diaquaoxoperoxy (2-pyridinecarboxylate-kN1, kO2)

375

(4)

List of Contributors

379

(8)

Reagent Formula Index

387

(4)

Subject Index

391

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Reagents for Direct Functionalization of C-H Bonds

Summary

Author Biography

Table of Contents

Supplemental Materials

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Reagents for Direct Functionalization of C-H Bonds

Summary

Author Biography

Table of Contents

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