128973-26-2

Upstream product

• 1564-64-3 9-Bromoanthracene 
• 1666-13-3 diphenyl diselenide 
• 716-53-0 9-chloroanthracene 
• 645-96-5 Benzeneselenol 
• 23974-72-3 sodium phenylselenide 

Relevant academic research and scientific papers

Orientational effect of aryl groups on77Se NMR chemical shifts: Experimental and theoretical investigations

The orientational effect of p-YC6H4 (Ar) on δ(Se) is elucidated for ArSeR, based on experimental and theoretical investigations. The effect is examined in the cases in which Se - CR in ArSeR is either in the Ar plane (pl)

Selenolation of Aryl Iodides and Bromides Enabled by a Bench-Stable PdI Dimer

The use of an air- and moisture-stable dinuclear PdI complex as an efficient catalyst for the formation of C(sp2)?SeR bonds is here reported. The privileged reactivity of the PdI dimer allows for the direct use of selenolates as nucleophiles in the cross-coupling. Although previous methodologies suffer from catalyst poisoning through the formation of Pd-ate complexes, the mechanistically distinct dinuclear PdI catalyst circumvents this challenge. A wide variety of aryl bromides and iodides were efficiently coupled under relatively mild reaction conditions with broad functional group tolerance. Mechanistic and computational data are presented in support of direct PdI reactivity.

Microwave-assisted synthesis of substituted phenanthrenes, anthracenes, acenaphthenes, and fluorenes

Rapid coupling reactions of polycyclic aromatic halides with various N-, S-, and Se-nucleophiles under focused microwave irradiation are described. Using this method, the desired products are obtained with good to excellent yields in a short reaction time. Crown Copyright

Electrochemically induced srn1 substitution in acetonitrile. Synthesis of arenes substituted by phenylseleno- and phenyltelluro groups

In MeCN, the direct or mediated cathodic reduction of unactivated ArBr (Ar = 4-biphenyl, 2-fluorenyl, 9-anthryl) in the presence of an equivalent of PhE- (E = Se, Te) leads to ArEPh in interesting isolated yields (53-74 %) by SNR1 substitution. The electrochemical synthesis of 9-phenylchalcogenoanthracene proceeds in better yields in MeCN than in DMSO. The 4,4′-disubstituted biphenyl PhSeC6H4C6H4SePh was prepared in 46 % yield in MeCN whereas its synthesis by photostimulation in liquid ammonia failed.

Electrochemical Determination of Absolute and Relative Reactivities of Phenyl Chalcogenide Anions toward Aryl Radicals

Absolute and/or relative reactivities of PhE- anions (E = Se, Te) toward the radicals resulting from the reductive cleavage of 9-bromoanthracene and 2- and 4-bromobenzophenone were determined by electrochemically stimulated SRN1 substitution in MeCN and Me2SO.Cyclic voltammetry and preparative-scale electrolyses were carried out under experimental conditions where the nucleophilic attack (rate constant k2) was competing only with H atom abstraction (rate constant kH) and so k2/kH ratios could be measured.Taking into account results previously published by Saveant et al. concerning kH and the reactivity of PhS- nucleophile toward aryl radicals, the following conclusions were drawn out.The absolute reactivity of PhSeNBu4 toward 9-anthryl radical is 12 times higher in MeCN (k2 = 8.1 x 109 M-1 s-1) than in Me2SO (k2 = 6.8 x 108 M-1 s-1).In Me2SO, the relative reactivities of PhSLi, PhSeLi, and PhTeLi are 1, 1.4, and 3.2.In MeCN the rate k2 is close to the diffusion limit in the nucleophilic attack of PhSeNBu4 and PhSNBu4 upon radicals corresponding to reduction of bromobenzophenone.