18255-05-5Relevant academic research and scientific papers
Zinc-mediated synthesis of tertiary alkyl selenides from tertiary alkyl halides
Krief, Alain,Derock, Michel,Lacroix, Damien
, p. 2832 - 2834 (2005)
Diorganyl selenides are efficiently synthesized from tertiary alkyl halides, selenols or selenolates and zinc dibromide as well as from diselenides in the presence of zinc. Georg Thieme Verlag Stuttgart.
A practical access to acyl radicals from acyl hydrazides
Bath, Sophie,Laso, Nieves M.,Lopez-Ruiz, Heraclio,Quiclet-Sire, Beatrice,Zard, Samir Z.
, p. 204 - 205 (2003)
Various acyl radicals can be generated from the corresponding acyl triphenylmethyldiazo derivatives, produced by in situ oxidation of hydrazide precursors with phenylseleninic acid.
A novel synthesis of benzyl sulfides and selenides via SM/BiCl3 system in aqueous media
Lu, Genliang,Zhang, Yongmin
, p. 4479 - 4484 (1998)
Benzyl sulfides and selenides are synthesized via reaction of benzyl bromide with disulfides and diselenides prorated by Srn/BiCl3 system in aqueous media in moderate to good yields.
Tandem homolytic addition/substitution sequences and their application to tin-free radical chemistry
Lobachevsky, Sofia,Schiesser, Carl H.,Gupta, Vijay
, p. 9077 - 9079 (2007)
Alkyl pent-4-enyl selenides (3a, b, e and f), pent-4-enylseleno benzoate (3c) and phenyl (pent-4-enylseleno)formate (3d) act as precursors of alkyl, acyl and oxyacyl radicals by reaction with diethyl 2-phenylselenomalonate (1) under photochemical conditio
Unusual Application for Phosphonium Salts and Phosphoranes: Synthesis of Chalcogenides
Moura, Igor M. R.,Tranquilino, Arisson,Sátiro, Barbara G.,Silva, Ricardo O.,De Oliveira-Silva, Diogo,Oliveira, Roberta A.,Menezes, Paulo H.
, p. 5954 - 5964 (2021/05/04)
A novel strategy for the synthesis of sulfides and selenides from phosphonium salts and thio- or selenesulfonates, commercially available compounds, is described. When phosphoranes were used in the reaction, different products were obtained. The methodology does not require the use of metals, reactive species, or anhydrous conditions to be performed.
Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light
Ji, Liangshuo,Qiao, Jiamin,Li, Ankun,Jiang, Zeyi,Lu, Kui,Zhao, Xia
, (2021/05/04)
We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.
O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol
Temperini, Andrea,Siciliano, Carlo
, (2020/06/17)
A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.
Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides
Li, Fuhai,Wang, Dan,Chen, Hongyi,He, Ze,Zhou, Lihong,Zeng, Qingle
, p. 13029 - 13032 (2020/11/07)
A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is
Rhodium-Catalyzed Carbene Transfer Reactions for Sigmatropic Rearrangement Reactions of Selenium Ylides
Jana, Sripati,Koenigs, Rene M.
supporting information, p. 3653 - 3657 (2019/05/24)
The rearrangement of selenium ylides is even today almost unexplored, although it would provide access to important organoselenium compounds with broad downstream applications. In this report, the first systematic study of sigmatropic rearrangement reactions of selenium ylides using a simple rhodium catalyst with catalyst loadings as low as 0.01 mol % is described. Selenium oxide pyrolysis of the rearrangement products gives access to important 1,1-disubstituted butadienes.
Metal-free synthesis of unsymmetrical organoselenides and selenoglycosides
Guan, Yong,Townsend, Steven D.
supporting information, p. 5252 - 5255 (2017/11/06)
A one-pot, metal-free procedure has been developed to synthesize unsymmetrical organoselenides. In the first step of the reaction, arylation of potassium selenocyanate (KSeCN) with an iodonium reagent proceeds in the absence of a metal catalyst to produce
