1694-07-1Relevant academic research and scientific papers
An electrochemical method for deborylative selenylation of arylboronic acids under metal- and oxidant-free conditions
Cai, Hu,Fu, Zhengjiang,Guo, Shengmei,He, Dongdong,Yi, Xuezheng,Yin, Jian
supporting information, p. 130 - 135 (2022/01/19)
An efficient protocol to synthesize aryl selenoethers through deborylative selenylation of widely available arylboronic acids has been established under electrochemical conditions in the absence of metal catalyst and external oxidant. The synthesis of bio
Synthesis and Reactivity Studies of a Series of Nickel(II) Arylchalcogenolates
Cordeiro, Lauren L.,Dmitrenko, Olga,Yap, Glenn P. A.,Riordan, Charles G.
, p. 6327 - 6338 (2021/05/06)
Two series of high-spin nickel complexes, [TpPh,Me]Ni(EAr) (E = O, Se, Te; Ar = C6H5) and [TpPh,Me]Ni(SeC6H4-4-X) (X = H, Cl, Me, OMe), were prepared by metathetical reaction of the nickel(II) halide precursor with sodium salts of the corresponding chalcogen, NaEAr. X-ray crystallographic characterization and spectroscopic studies have established the geometric and electronic structures of these complexes. The observed spectroscopic and structural characteristics reveal distinct trends in accordance with the variation of the identity of the arylchalcogenolate and para substituent. Reaction of the [TpPh,Me]Ni(EAr) complexes with methyl iodide proceeded readily, producing the corresponding methylarylchalcogen and [TpPh,Me]NiI. A kinetic and computational analysis of the reaction of [TpPh,Me]Ni(SeC6H5) with MeI supports that the electrophilic alkylation reactions occur via an associative mechanism via a classical SN2 transition state.
A general and green procedure for the synthesis of organochalcogenides by CuFe2O4 nanoparticle catalysed coupling of organoboronic acids and dichalcogenides in PEG-400
Kundu, Debasish,Mukherjee, Nirmalya,Ranu, Brindaban C.
, p. 117 - 125 (2013/04/10)
A general and efficient procedure has been developed for the synthesis of organochalcogenides (selenides and tellurides) by a simple reaction of organoboronic acids and dichalcogenides catalysed by CuFe2O 4 nanoparticles in PEG-400 without any ligand. This protocol offers the scope for access to a wide spectrum of chalcogenides including diaryl, aryl-heteroaryl, aryl-styrenyl, aryl-alkenyl, aryl-allyl, aryl-alkyl and aryl-alkynyl versions. The catalyst is magnetically separable and recyclable eight times without any loss of appreciable catalytic activity. The products are obtained in high purities after evaporation of solvent followed by filtration column chromatography. The Royal Society of Chemistry.
Synthesis of arylselenide ethers by photoinduced reactions of selenobenzamide, selenourea and selenocyanate anions with aryl halides
Bouchet, Lydia M.,Pe?é?ory, Alicia B.,Argüello, Juan E.
experimental part, p. 969 - 972 (2011/03/20)
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.
Preparation and interconversion of phenylselenenylated and alkyjlselenenylated aromatic compounds
Engman, Lars,Eriksson, Per
, p. 861 - 871 (2007/10/03)
Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treated with methylselenenyl sulfate, veratrole an
A GENERAL PROCEDURE FOR THE SYNTHESIS OF METHYLTHIO-, METHYLSELENO- AND METHYLTELLURO-SUBSTITUTED AROMATIC COMPOUNDS
Engman, Lars,Hellberg, Jonas S. E.
, p. 357 - 366 (2007/10/02)
A one-pot procedure is described which allows the facile introduction of one or two methylchalcogeno groups into a variety of monobromo or dibromo aromatics.The bromo compounds were converted to their corresponding lithio derivatives by treatment with t-butyllithium in tetrahydrofuran at -78 deg C, and these derivatives were then treated, at ambient temperature with elemental sulfur, selenium, or tellurium.The resulting lithium thiolates, selenolates and tellurolates were finally methylated with methyl iodide to afford good yields (typically 50-80percent) of the various methylchalcogeno-substituted aromatic compounds.The procedure could not be used for the synthesis of ortho-disubstituted compounds, or for the simultaneous introduction of three methylchalcogeno groups.
Methyl Transfers. 10. The Marcus Equation Application to Soft Nucleophiles
Lewis, Edward S.,McLaughlin, Mark L.,Douglas, Thomas A.
, p. 6668 - 6673 (2007/10/02)
The Marcus equation to methyl transfers is shown to cover reactions of " soft" nucleophiles, although small discrepancies occur.Rates and equilibria are reported for a series of reactions of arylmethylselenides with (p-chlorophenyl)dimethylselenonium ion.Experimental reaction rates between "hard" methylating agents and "soft" nucleophiles show small deviations from the calculated values, mostly but not always in the direction predicted by the HSAB principle.The Marcus equation fails to explain the previously reported "inversion" of reaction rates of 4-nitrothiophenoxide and of 4-nitrophenoxide with methyl iodide and dimethyl sulfate.Identity rates for dimethyl sulfate, methyl methanesulfonate (using 3He), methyl iodide (using 125I), and methyl triflate (using 35S) in sulfolane are reported.
SYNTHESIS, STRUCTURE, AND PROPERTIES OF COMPOUNDS WITH A CHALCOGEN-NITROGEN BOND. V. N-TRIFLUOROACETYL-Se-ARYL-Se-METHYLSELENIMIDES
Naddaka, V. I.,Krasnov, V. P.,Minkin, V. I.
, p. 432 - 436 (2007/10/02)
The IR and UV spectra of a series of N-trifluoroacetyl-Se-aryl-Se-methylselenimides were studied.The molecules of these compounds, like those of N-acylsulfimides and N-acyltelurimides with similar structures, have a bipolar structure, in which the negative charge is distributed through the bond system of the N-trifluoroacetyl group.
