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1
Index
1. Introduction
1
1.1. Some physical properties of tellurium
1
1.2. Relevant monographs and review articles
1
2-Preparation of the more important inorganic tellurium reagents
3
2.1. Tellurium tetrachloride
3
2.2. Tellurium dioxide
4
2.3. Alkali metal tellurides (Te2-Cat2+)
4
2.3.1. From the elements (2Na + Te - Na2Te)
4
2.3.2. From tellurium and reducing agents (Te→ Te2-)
4
2.3.3. From tellurium and non-reducing bases
5
2.4. Alkali metal ditellurides (Na2Te2)
5
2.4.1. From the elements (2Na+2Te→Na2Te2)
5
2.4.2 From tellurium and reducing agents
5
2.5 Hydrogen telluride (H2Te)
5
2.6 Sodium hydrogen telluride (NaHTe)
6
3. Preparation of the principal classes of organic tellurium compounds
7
3.1. Diorganyl tellurides
11
3.1.1. Symmetrical dialkyl tellurides
11
3.1.1.1. From alkali tellurides and alkylating agents
11
3.1.1.2. From bis(triphenylstannyl) telluride and alkylating reagents
15
3.1.2. Symmetrical diaryl tellurides
16
3.1.2.1. From alkali tellurides and non-activated aryl halides
16
3.1.2.2.
From
sodium
telluride
or
sodium
O,O-diethyl
18
phosphorotellurolate and arenediazonium fluoroborates
3.1.2.3 From potassium tellurocyanate and arenediazonium fluoroborates 19
3.1.2.4. From tellurium (IV) halides and arylmagnesium halides
19
3.1.2.5. From elemental tellurium and diarylmercury compounds
20
3.1.2.6 From diaryl ditellurides by extrusion of a tellurium atom
20
3.1.2.7. Bis-(phenylethynyl)telluride as Te2+ equivalent
21
3.1.3. Unsymmetrical tellurides
22
3.1.3.1. From sodium telluride and two different alkyl halides
22
3.1.3.2. From organyl tellurolates and alkylating agents
23
3.1.3.3. By addition of aryl tellurolates to electrophilic alkenes
27
2
3.1.3.4. From organyl tellurolates and arylating agents
28
3.1.3.5. From diorganyl ditellurides or arenetellurenyl halides and 28
organometallic reagents
29
3.1.3.6. Additional methods
3.1.4. Diorganyl tellurides by reduction of diorganyltellurium dihalides
32
3.2. Diorganyl ditellurides
34
3.2.1. From sodium ditelluride
34
3.2.1.1. From sodium ditelluride and alkylating agents
34
3.2.1.2. From sodium ditelluride and aryl halides
36
3.2.2. By oxidation of organotellurols or organotellurolates
37
3.2.3. By reduction of organotellurium trichlorides
39
3.2.3.1. Reduction of -carboxyalkyltellurium trichlorides
39
3.2.3.2. Reduction of -alkoxyalkyltellurium trichlorides
40
3.2.3.3. Reduction of aryltellurium trichlorides
40
3.2.4. Diaryl ditellurides from aryl boronic acids
41
3.3. Organyl tellurols
42
3.4. Bis-organyl telluromethanes
43
3.5. Organyl tellurium trihalides
44
3.5.1. Organyltellurium trichlorides from tellurium tetrachloride and 44
organic substrates
3.5.1.1. From tellurium tetrachloride and ketones and carboxylic 44
anhydrides
3.5.1.2. From tellurium tetrachloride and alkenes
44
3.5.1.3. From tellurium tetrachloride and arenes
46
3.5.1.4. From tellurium tetrachloride and arylmercury chlorides
47
3.5.2. By chlorinolysis of diorganyl ditellurides
48
3.5.3. Organyltellurium tribromides and triiodides by halogenolysis of the 48
corresponding ditellurides
3.5.4. Additional method. Preparation of organyltellurium trichlorides and 49
tribromides by the reaction of tetraorganyltin compounds with
tellurium tetrachloride and tetrabromide
3.6. The products of the hydrolysis of aryl tellurium trihalides
50
3.7. Aryl tellurenyl halides
51
3.8. Aryl Tellurenyl pseudohalides. aryl tellurocyanates
53
3.9. Diorganyl tellurium dihalides
53
3.9.1. From elemental tellurium
53
3.9.2. From tellurium tetrahalides (or tellurium dioxides)
54
3
3.9.2.1. With ketones and carboxylic acid anhydrides
54
3.9.2.2. With alkenes
54
3.9.2.3. With arenes
54
3.9.2.4. With arylmercury chlorides
55
3.9.2.5. With arenediazonium salts
55
3.9.3. From organyltellurium trihalides
56
3.9.3.1. With ketones
56
3.9.3.2. With alkenes
57
3.9.3.3. With arenes
58
3.9.3.4. With organylmercury chlorides
58
3.9.4. By addition of halogens to diorganyl tellurides
59
3.9.5. Additional methods
60
3.9.5.1. Reaction of elemental tellurium with arenediazonium salts
60
3.9.5.2. Reaction of TeO2/LiCI with aryl hydrazines
60
3.9.5.3. Reaction of diaryl ditelluride with arenediazonium salts/CuCl2
60
3.10. Diorganyl telluroxides
61
3.10.1.Hydrolysis of diaryltellurium dihalides
62
3.10.2. Oxidation of diaryl tellurides
62
3.11. Telluroesters
62
3.12. Aryl telluroformates
65
3.13. Telluroglucopyranosides
66
3.14. Water soluble diorganyl tellurides
66
3.15. Dihaloaryltelluro cyclopropanes
67
3.16. Vinylic tellurides and ditellurides
67
3.16.1. Starting from nucleophilic tellurium
67
3.16.1.1. Addition of alkali tellurides to acetylenes
67
3.16.1.2. From organyltellurols or tellurolates and terminal acetylenes
69
3.16.1.3. From organyl tellurolate (and telluride) anions and vinyl 74
bromides
3.16.1.4. From vinylic tellurolate anions and alkyl halides
75
3.16.1.5. From organotellurolate anions and activated vinylic halides
76
3.16.1.6. From organyl tellurolates and electrophilic acetylenes
78
3.16.1.7. Tanden vicinal difunctionalization of alkynes
79
3.16.1.8. Telluroacylation of terminal alkynes
80
4
3.16.2. Starting from electrophilic tellurium
80
3.16.2.1. By addition of tellurium tetrahalides and aryltellurium trihalides 80
to acetylenes
3.16.2.2. From organyltellurenyl halides and vinylic Grignard reagents
82
3.16.2.3. From vinyltellurenyl iodides and Grignard reagents
83
3.16.3. Via radical reactions
83
3.16.4.Reduction of acetylenic tellurides
85
3.16.5.Vinylic tellurides via olefination reactions
86
3.16.5.1.Horner-Emmons route
86
3.16.5.2. Wittig route
87
3.16.6. Vinyl tellurides via borane chemistry
89
3.16.7. Telluro (seleno)ketene acetals, 1-seleno-2-telluro-ethenes,
90
telluro ketene acetals, telluro (stannyl)-ketene acetals and
telluro(thio)ketene acetals
3.16.8. The behaviour of vinylic teIlurides toward several reagents and 99
reaction conditions used in organic synthesis
3.17. Acetylenic tellurides
103
3.17.1. From nucleophilic tellurium reagents
103
3.17.1.1. Sodium ethynyl tellurolates
103
3.17.1.1.2. Lithium alkyl and ethynyl tellurolates
103
3.17.2. From electrophilic tellurium reagents
104
3.17.2.1. From alkynyl Grignard and lithium compounds and organyl 104
tellurenyl halides
3.17.2.2. From tellurium tetrachloride and alkynyllithium compounds
106
3.17.3. Synthesis of internal acetylenes from vinylic tellurides
107
3.18. Allenic and propargylic tellurides
107
4. Tellurium in organic synthesis
110
4.1. Reductions
110
4.1.1. Reduction of carbonyl compounds
110
4.1.1.1. With hydrogen telluride
110
4.1.1.2. With phenyltellurol
110
4.1.1.3. With diisobutyl telluride/titanium (IV) chloride
112
4.1.1.4. With sodium telluride in 1-methyl-2-pyrrolidinone
112
4.1.2. Selective reduction of -unsaturated carbonyl compounds
113
4.1.3. Reduction of conjugated arylalkenes and arylalkynes
114
4.1.4. Reduction of imines and enamines
115
5
4.1.5. Reductive desulphuration of aromatic thioketones
116
4.1.6. Reduction of nitro compounds
116
4.1.7. Reduction of other nitrogenated compounds
120
4.1.8 Deselenylation of -seleno carboxylic compounds
122
4.1.9. Deoxygenation of oxiranes with alkali O,O-dialkyl
phosphorotellurolates
4.1.10. Reductive opening of oxiranes with sodium hydrogen telluride and
sodium telluride
4.1.11. Correlate reaction-tellurium-mediated resolution of racemic allyl
alcohols
4.1.12. 1,2-Elimination in vicinal disubstituted substrates
123
4.1.12.1. Debromination of vic-dibromides with tellurium reagents
127
4.1.12.2. Desulfonation of vic-dimesylates and vic-ditosylates
131
4.1.13. Reductive fission of carbon-heteroatom bonds
132
123
125
127
4.1.13.1. Reductive removal of electronegative  substituents from 132
ketones, acids and derivatives
4.1.13.2. Dehalogenation of polyhalogenated organic compounds
136
4.1.13.3. Reductive removal of tertiary nitro groups
136
4.1.13.4. Reductive dealkylation of quaternary ammonium salts
137
4.1.13.5. Reductive desulphonation of -ketosulphones
137
4.1.13.6 Desulphonylative condensation of -cyanosulphones with
aldehydes
4.1.13.7. Correlate reaction - Desulphonylation of -nitrosulphones
138
139
4.1.13.8. Monodesulphuration of diaryl thioketals and bis-sulphenylated
139
-dicarboxyl compounds, diorganyl trisulfides and disulfides
4.2. Tellurium-mediated formation of anionic species and their reactions 143
with electrophiles
4.2.1. Reformatsky-type reactions
143
4.2.2. Knoevenagel-type reaction
144
4.2.3. Pinacol reaction
145
4.2.4. Alkylidenation of aldehydes and cyclopropanation of  145
unsaturated carbonyl compounds with dibromomalonic esters
4.2.5. Telluride-assisted sulphenylation and sulphonylation reactions
146
4.2.6. Telluride-mediated aldehyde methylenation
148
4.2.7 Miscellaneous
149
4.3. Deprotection of organic functionality by tellurium reagents
150
4.3.1. Regeneration of carboxylic acids:cleavage of carboxylic esters
150
4.3.1.1. Alkyl carboxylates
151
6
4.3.1.2. Phenacyl carboxylates
152
4.3.1.3. Allyl carboxylates
152
4.3.1.4. 2-Haloethyl carboxylates
153
4.3.2. Regeneration of Phenols
154
4.3.2.1. Cleavage of aryl carboxylates and carbonates
154
4.3.2.2. Cleavage of aryl haloacetates
155
4.3.2.3. Cleavage of phenyl allyl ethers
156
4.3.3. Regeneration of amines by cleavage of trichloro-t-butylcarbamates
156
4.4. Oxidation of organic substances by means of tellurium reagents
157
4.4.1. Bis(p-methoxyphenyl) telluroxides as a mild and selective oxidizing 157
reagent
4.4.1.1. Conversion of thio- and selenocarbonyl compounds to their oxo 157
analogues
4.4.1.2. Conversion of tertiary phosphines to tertiary phosphine oxides
159
4.4.1.3. Conversion of phenyl isothiocyanate to diphenylurea
159
4.4.1.4. Conversion of thiourea to ureas
159
4.4.1.5. Conversion of thiols to disulfides
159
4.4.1.6. Conversion of o- and p-diphenols to quinones
160
4.4.1.7. Conversion of acylhydrazines to acylhydrazides
160
4.4.1.8. Conversion of N-phenylhydroxylamine to nitrosobenzene
160
4.4.1.9.
Conversion
of
benzophenone
hydrazone
diphenyldiazomethane
4.4.2. Polymer-supported bis(p-methoxyphenyl) telluroxide
to 160
161
4.4.3. Bis(p-methoxyphenyl) telluride as a mediator in an electrolytic
process
4.4.4. Bis(p-methoxyphenyl) tellurone
162
4.4.5. Sodium tellurite as oxidizing agent for thiols
164
4.4.6. TeCl4 promoted oxidation of trialkylphosphites
165
4.4.7. Arenetellurinic anhydrides
166
4.4.8. Reaction of oxidizing tellurium reagents with the C=C bond
168
163
4.4.8.1. Epoxidation of olefins catalyzed by polystyrene-supported 168
tellurinic acid
4.4.8.2. Diacetoxylation of olefins
169
4.4.8.3. Methoxytellurenylation and dimethoxylation of olefins
173
4.4.8.4. Aminotellurinylation of olefins and related reactions
174
4.5. Organotellurium-based ring closure reactions
178
4.5.1. Tellurolactonization of unsaturated carboxylic acids
179
7
4.5.1.1. With aryltellurium trichlorides
179
4.5.1.2. With benzenetellurenyl nitrobenzenesulphonate
180
4.5.1.3. With diaryl tellurium dihalides
180
4.5.1.4. Tellurolactonization of -allenic acids with phenyltellurenyl 181
chloride
4.5.1.5. Reductive detelluration of tellurolactones
181
4.5.2.
Cyclotelluroetherification of
allylphenols
4.5.2.1. With aryltellurinyl acetates
unsaturated
alcohols
and
183
183
4.5.2. With aryltellurium trichlorides
184
4.5.2.3. With benzenetellurenyl nitrobenzenesulphonate
185
4.5.2.4. With TeO2/HOAc/LiCl or TeO2/HCl
186
4.5.2.5. With diaryl tellurium dihalides
187
4.5.2.6. Synthetic utility of the telluroetherification reactions
187
4.5.3. Tellurocyclofunctionalization of alkenylsubstituted -dicarbonyl 188
compounds
4.5.4. Tellurocyclization of olefinic carbamates
190
4.6. Conversion of organotellurium compounds into tellurium-free organic
compounds
4.6.1. Detelluration of organotellurium compounds with the formation of
new C-C bonds (carbodetelluration)
4.6.1.1. Synthesis of biaryls by Raney-Ni catalyzed homocoupling of
diaryltellurium dichlorides and aryltellurium trichlorides
4.6.1.2. Pd(0) catalyzed homocoupling of diorganyl tellurides (and
ditellurides)
4.6.1.3. Correlate reactions
191
4.6.1.4. Olefin arylation by Pd(II) catalyzed carbodetelluration of
aryltellurium compounds
4.6.1.5. Pd(II) catalyzed cross-coupling reactions of aryl tellurides with
alkenes
4.6.1.6. Ni(II) or Co(II) Catalyzed cross-coupling of Grignard reagents
with organic tellurides
4.6.1.7. Palladium and copper catalyzed cross-coupling of
organotellurium dichlorides with organostannanes and
organoboronic acids.
4.6.1.8. Palladium catalyzed cross-coupling of organo-tellurium
compounds with hypervalent iodonium salts
4.6.1.9. Detellurative carbonylation of organotellurium compounds:
preparation of carboxylic acids
4.6.1.10.
Synthesis
of
enones
and
cyclopropanes
from
bis(oxoalkyl)tellurium dichlorides
4.6.1.11. Conversion of telluroesters into ketones
193
4.6.2. Replacement of the tellurium moiety by other functionalities
198
191
191
191
192
194
194
194
195
196
197
198
8
4.6.2.1. By Amino Group - Allylic amine by imination of allylic tellurides
198
4.6.2.2. By Hydroxy Group - Hydrolysis of telluroesters to carboxylic 199
acids and esters
4.2.2.3. By halogens
199
4.6.2.4. By the methoxy group
206
4.6.2.5. Reductive detelluration of tellurides by triphenyltin hydride
208
4.7. Synthesis of olefins
210
4.7.1. By telluroxide elimination
210
4.7.2 Correlate method: reaction of alkyl phenyl tellurides with 214
chloramines-T
4.7.3. From telluronium ylides
215
4.7.3.1. Stabilized telluronium ylides
215
4.7.3.2. Semi-stabilized and non-stabilized telluronium ylides
218
4.7.3.3. Correlate reaction: the reaction of telluronium salts with carbonyl 222
compounds mediated by organolithium reagents - formation of
secondary alcohols
4.7.4. Tellurium-catalyzed decomposition of -lithiated benzylic 224
sulphones into 1,2-diarylethylenes
4.8. Transmetallations reactions
227
4.8.1. Lithium tellurium exchange: generation of organolithium reagents
226
4.8.1.2. Acyl- and aroyllithim compounds
233
4.8.1.3. Heterosubstituted methyllithium compounds
234
4.8.1.4. Ferrocenyltellurium derivatives
236
4.9. Reactivity and synthetic applications of vinylic tellurides
237
4.9.1. Vinylcuprates by copper-tellurium exchange
237
4.9.1.1. Conjugate addition to enones
237
4.9.1.2. Conjugate addition of higher order cyanocuprates to enone, 240
followed by O-functionalization
4.9.1.3. Reaction with epoxides
243
4.9.1.4. Reaction with bromoalkynes
244
4.9.1.5. Synthesis of (-)-Macrolactin A
245
4.9.2. Tellurium-zinc and tellurium-alumminum exchange
245
4.9.3. Coupling reactions
248
4.9.3.1 Pd(II) catalyzed homocoupling of vinyl tellurides
248
4.9.3.2. Pd(II) catalyzed cross-coupling of vinylic tellurides with alkenes
249
4.9.3.3. Ni(II) or Cu(I) catalyzed cross-coupling of vinyl tellurides with 250
Grignard reagents
9
4.9.3.4. Pd(II) and Ni(II) catalyzed Sonogashira type cross-coupling of 252
vinyl tellurides and vinyl tellurium dichlorides with terminal
alkynes
4.9.3.5. Pd/Cu catalyzed cross-coupling of vinylic tellurides with organyl 254
zinc reagents
4.9.3.5. Detellurative carbonylation of vinylic tellurides
256
4.10. Free radical chemistry
258
4.10.1. Telluride ion-promoted coupling of allylic halides
258
4.10.2. Organyl tellurides as exchangers of carbon radicals
259
4.10.2.1. Tellurium-mediated addition of carbohydrates to olefins
259
4.10.2.2. Intramolecular radical cyclization
260
4.10.3. Reactions of tetraorganyl tellurium with acetylenes
262
4.10.4. Telluroesters as source of acyl radicals
263
4.10.5. Aryl telluroformates as precursors of oxyacyl and alkyl radicals
268
4.10.6. Aryltelluroformates as precursors of selenium containing 268
heterocycles
4.10.7. Allyloxy and 2-propargyloxy alkyl tellurides as precursors of 269
tetrahydrofuran derivatives
4.10.8. Telluroglycosides as source of glycosyl radicals
270
4.10.9. Radical mediated group transfer imidoylation with isonitriles
271
4.10.10.
273
Three component coupling of silyltellurides, carbonyl
compounds and isocyanides
4.10.11. Synthesis of substituted quinones via organotellurium
compounds
4.10.12. Thiotelluration of vinyl cyclopropanes. Thio and selenotelluration
of acetylenes
4.10.13. Perfluoroalkyltelluration of terminal olefins and alkynes
275
277
279
4.10.14. Synthesis of indole derivatives via radical cyclization of N-(ortho 280
ethynylbenzene)-phenyltelluro trifluoro acetimidates
4.10.15. Organotellurium compounds as initiators for controlled living 281
radical polymerization
5. Telluroheterocycles
283
5.1. Tellura-3,5-cyclohexanedione dichlorides (3,5-dioxotellurane-1,1- 283
dichlorides
5.2. Oxa and 1-thia-4-telluranes
283
5.3. Tellurophenes
283
5.3.1. Preparation
284
5.3.1.1. From alkali metal tellurides
284
5.3.1.2. From tellurium tetrachloride
285
5.3.1.3. From 1,4-dibutyltellurobutadiene
285
10
5.3.1.4. From butyltellurobutenines
286
5.3.2. Reactions of tellurophene
287
5.3.2.1. Via 2-lithiotellurophene-2-substituted derivatives
287
5.3.2.2. Formylation
287
5.3.2.3. Acetylation
287
5.3.2.4. Chloromethylation
288
5.3.2.5. Acetoxymercuriation
288
5.3.2.6. Modifications of the functionalized tellurophenes
288
5.3.2.7. Formation of complexes
289
5.3.2.8. Removal of tellurium from the ring
289
5.4. 1-Benzotellurophenes
289
5.4.1. Preparation
289
5.4.1.1. From tellurium
289
5.4.1.2. From TeO2
290
5.4.1.3. Via cyclization of ortho acetyl or formyl substituted phenyl telluro 291
compounds
5.4.1.4. From o-phenylethenyl tellurium trichloride
292
5.4.2.
Reactions
of
1-benzotellurophene
dihydrobenzotellurophene
5.4.3. Ring cleavage of the tellurophene ring
and
3-oxo-2,3- 292
294
5.5. Benzotellurepines
295
5.5.1. Preparation
295
5.5.2. Reactions
297
5.6. 2-Benzotellurophenes
297
5.6.1. Preparation
297
5.7. Telluro[3,4-c]thiphene
298
5.7.1. Preparation
298
5.8. Dibenzotellurophenes
299
5.8.1. Preparation
299
5.8.1.1. From tellurium
299
5.8.1.2. From tellurium dichloride
300
5.8.1.3. From tellurium IV halides
300
5.8.1.4. From bis[2,2´-biphenyldiyl]tellurium
301
5.8.2. Reactions
301
5.8.2.1. Halogenation
301
11
5.8.2.2. Cleavage of Te-C bond
302
5.9. Naphtothiatellurole, Naphtoselenatellurole, Naphtoditellurole
302
5.9.1. Preparation
302
5.10. 2H-1,3-Ditelluroles
303
5.10.1. Preparation
303
5.10.2. Reactions
304
5.11. Tetratellurafulvalenes
305
5.11.1. Preparation
305
5.12. Tellurin and derivatives 4-H-tellurins and 4-oxo-4-H-tellurins 306
(telluropyran-4-ones)
5.12.1. Preparation
306
5.12.2. Reactions
308
5.13. 2H-1-Benzotellurin
309
5.13.1. Preparation
309
5.14. 4H-1-Benzotellurins and 4-oxo-4H-benzotellurins
309
5.14.1. Preparation
309
5.15. Telluroxanthenes/Telluroxanthones and derivatives
310
5.15.1. Preparation
311
5.15.2. Reactions
311
5.16. Phenoxatellurins
313
5.16.1. Preparation
313
5.17. Phenothiatellurins/Phenoselenotellurins
314
5.17.1. Preparation
314
5.18. Telluranthrenes
315
5.18.1. Preparation
315
5.18.1.1. From tellurium
315
5.18.1.2. From sodium telluride
316
5.19. Bis-thieno-1,4-ditellurins
317
5.19.1. Preparation
317
5.20. 1,4-Tellurino-1,4-tellurins
317
5.20.1. Preparation
317
5.21. Benzene fused heterocycles containing tellurium, selenium and 318
sulfur
5.21.1. Preparation
318
5.22. 1,5-Ditelluracyclooctane and 5H,7H-dibenzo[b,g][1,5]tellurothiocin
319
12
5.22.1. Preparation
319
5.23. Ditellurane derivatives
320
5.23.1. Preparation
320
5.24. Reductive dimerization of telluro- and selenoxanthone
321
5.25. Tellurosteroids
322
5.26. 21,21-Dihalo-21-telluroporphyrin
322
6. Toxicology of organotellurium compounds
326
7. Pharmacology of organotellurium compounds
328
7.1. Chemopreventive activity
329
8. Miscellaneous
332
8.1. Some additional applications of TeCl4
332
8.1.1. Preparation of -methylene ketones
332
8.1.2. Olefin inversion by syn-chlorotelluration/anti-dechlorotelluration
332
8.1.3. TeCl4 as a catalyst for dithioacetalization and ketalization
333
8.1.4. TeCl4 as reagent for the conversion of alcohols to alkyl chlorides
334
and as a Lewis acid catalyst for aromatic alkylation
8.1.5. TeCl4-promoted rearrangement of cycloheptatrienes to benzylic
alcohols
8.1.6. TeCl4 as catalyst for cationic oligo- and polymerization reactions
335
8.2. -Hydroxyalkylation of -unsaturated compounds
336
8.3. Conversion of allylsilane into allylamines via phenyltellurinylation
336
335