One-pot synthesis of bromodifluoroacetimidoyl halides and its Suzuki coupling reactions with aryl boronic acids

N-aryl bromodifluoroacetimidoyl halides were prepared by the reaction of bromodifluoroacetic acid, triphenyl phosphine, p-arylaniline and triethylamine in tetrachloromethane in good yields. Palladium-catalyzed cross-coupling reaction of N-aryl bromodifluoroimidoyl iodide with arylboronic acids was realized to afford bromodifuoromethyl ketimine in good yields.     

One-pot synthesis of symmetrical and unsymmetrical aryl sulfides by Pd-catalyzed couplings of aryl halides and thioacetates

Aryl sulfides were obtained from the coupling reaction of S-aryl (or S-alkyl) thioacetates and aryl bromides in the presence of palladium catalyst. This reaction method enables the one-pot synthesis of symmetrical and unsymmetrical diaryl sulfides by employing potassium thioacetate with aryl iodides and aryl bromides.     

Copper oxide nanoparticles catalyzed synthesis of aryl sulfides via cascade reaction of aryl halides with thiourea

Recyclable copper oxide nanoparticles catalyzed simple and highly efficient protocol for the synthesis of symmetrical aryl sulfides was developed by the cross-coupling of aromatic halides with inexpensive and commercially available thiourea which was used as an effective sulfur surrogate. The present cross-coupling protocol of thiourea, via cascade reaction with various substituted aryl halides, producing desired aryl sulfides, has an added advantage of avoiding foul-smelling thiols.     

One-pot efficient synthesis of disulfides from alkyl halides and alkyl tosylates using thiourea and elemental sulfur without contamination by higher polysulfides

An efficient and odorless synthesis of disulfides from alkyl halides using thiourea and elemental sulfur in the presence of sodium carbonate in wet polyethylene glycol (PEG 200) at 40 °C without contamination by higher polysulfides has been developed. This procedure was then extended to preparation of disulfides from alkyl tosylates at 70 °C.     

Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides

Selenobenzamide (⁻SeCNH(Ph), 1), selenourea (⁻SeCNH(NH₂), 2) and selenocyanate (⁻SeCN, 3) anions afford areneselenolate ions (ArSe⁻) under photostimulation in the presence of tert-butoxide or 2-naphthoxide ions as electron donors (entrainment conditions) in DMSO. In a ‘one-pot’ procedure, ArSe⁻ anions can be trapped by a subsequent aliphatic nucleophilic substitution giving aryl methyl selenides in good to excellent yields (67-100%). This simple approach is compatible with electron-donating and electron-withdrawing substituents, such as nitro and carbonyl groups.     

One-pot thioetherification of aryl halides with thiourea and benzyl bromide in water catalyzed by Cu-grafted furfural imine-functionalized mesoporous SBA-15

Surface functionalization of SBA-15 followed by its reaction with Cu(OAc)(2) has been carried out to develop a new Cu-grafted functionalized mesoporous material, which catalyzes one-pot three component coupling of different aryl halides with thiourea and benzyl bromide in aqueous medium to produce aryl thioethers in very good yields (80-88%).     

CuI/L-proline-catalyzed coupling reactions of aryl halides with activated methylene compounds

[reaction: see text] The arylation of ethyl acetoacetate, ethyl benzoyl acetate, and diethyl malonate under the catalysis of CuI/L-proline in DMSO proceeds smoothly at 40-50 degrees C in the presence of Cs2CO3 to provide the 2-aryl-1,3-dicarbonyl compounds in good yields. Both aryl iodides and aryl bromides are compatible with these reaction conditions.     

Effective heterogeneous palladium catalysis of the reactions of organoboron compounds with aryl halides

Reactions of [Ph₄B]Na and ArB(OH)₂ with aryl halides are effectively catalyzed by heterogeneous palladium catalysts (PdCl₂C, Pd(0)/C, and palladium black) to give cross-coupling products in high yields. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1399–1401, July, 1997.     

Photochemical vs. electrochemical electron-transfer reactions. one-electron reduction of aryl halides by photoexcited anion radicals

Electrochemical reduction of aryl halides generally leads to expulsion of halide ion. The product aryl radical is unavoidably further reduced. In contrast, reduction of aryl halides by photoexcited anion radicals may be stopped at the aryl radical stage owing to the bimolecular nature of electron-transfer reactions. We have tested this hypothesis by photoinducing electron-transfer from anthraquinone anion radical to several aryl halides. For each halide it was possible to trap the corresponding radical by anthracene forming stituted 9-phenylanthracenes.     

Reaction of sulfur halides with unsaturated compounds

Conclusions Oxidation of 2,9-dichloro-13-thiabicyclo[8.2.1]cis-5-tridecene with tert-amyl hydroperoxide leads to the respective exo-sulfoxide and also to a derivative of 13-thiabicyclo[7.3.1]cis-5-tridecene, which is a product from rearrangement with enlargement of the thiacyclopentane ring to a thiacyclohexane ring.See [1] for Communication 11.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 384–389, February, 1976.     

One-pot primary aminomethylation of aryl and heteroaryl halides with sodium phthalimidomethyltrifluoroborate

A one-pot primary aminomethylation of aryl halides, triflates, mesylates, and tosylates via Suzuki-Miyaura cross-coupling reactions with sodium phthalimidomethyltrifluoroborate followed by deamidation with ethylenediamine is reported.     

Cross-coupling reactions of arylsilanols with substituted aryl halides

[reaction: see text] The palladium-catalyzed cross-coupling of arylsilanols with aryl iodides and aryl bromides (in the presence of cesium carbonate) furnished various biaryl products in high yield. An extensive series of optimizations led to the identification of key variables, including activator, solvent, catalyst, and hydration level, that influence the rate and selectivity of the process. Manipulation of these features provided an effective coupling method of wide scope and generality.     

Photochemical reactions of acyl iodides with aryl halides

Photochemical reactions of acyl iodides RC(O)I (R = Me, Ph) with aryl halides, fluoro-, chloro-, and bromobenzenes, 1,4-dibromobenzene, 2- and 3-bromotoluenes, and 4-bromo-1,2-dimethylbenzene, were studied. Acetyl iodide reacted with chloro- and bromobenzenes and 1,4-dibromobenzene according to the exchange pattern to give iodobenzene and 1,4-diiodobenzene, respectively. No halogen exchange was observed in the reactions of acetyl iodide with fluorobenzene and hexafluorobenzene. Benzoyl iodide failed to react with chloro- and brombenzene under UV irradiation but underwent polycondensation with formation of black nonfusible oligomers which were found to possess paramagnetic and semiconducting properties. Ultraviolet irradiation of a mixture of MeCOI with 2- or 3-bromotoluene, as well as with 4-bromo-1,2-dimethylbenzene, also led to the formation of polymeric products as a result of polycondensation of aryl iodides formed initially via replacement of bromine by iodine. Irradiation of benzoyl iodide in 2- or 3-bromotoluene involved recombination of benzoyl radicals to give benzil as the only product.     

Zeo-click synthesis: Cu-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds

Cu^I-zeolites proved to be an efficient heterogeneous catalyst for the one-pot two-step synthesis of triazoles from halides or tosylates, sodium azide, and alkynes. The step and atom economies of this cascade reaction as well as water used as solvent and catalyst recycling make such synthesis a trully green process. With selected substrates, the peculiar roles of Cu^I-zeolites as catalysts were highlighted.     

Copper-catalyzed synthesis of primary arylamines via cascade reactions of aryl halides with amidine hydrochlorides

We have developed an efficient method for the synthesis of primary arylamines from aryl halides using amidine hydrochlorides as the ammonia surrogates. The protocol uses 10 mol % CuI as the catalyst, 20 mol % L-proline as the ligand, Cs2CO3 as the base, and DMF as the solvent and proceeds the sequential coupling of aryl halides with amidine hydrochlorides and hydrolysis of intermediates to give the target products. This is a convenient, inexpensive, and practical approach to primary arylamines.     

One-pot synthesis of aryl biaryl sulfones

Synthesis of aryl biaryl sulfones 3 with good yields is described. The one-pot efficient synthetic route is carried by the NaH-mediated tandem [C3+C3] annulations of cinnamaldehydes 1 and propargylic sulfones 2 under the boiling THF conditions.