A New Method for the Reductive Cleavage of Se-Se Bond by Titanocene Dichloride Isobutylmagnesium Bromide System and Its Application in Synthesis of Selenoester

A Convenient and Stereoselective Synthesis of (E)-Vinylseleno Zirconocenes and (E)-Vinylic Selenol Esters

“…Recently transition metal selenolates have been widely used in synthesis of selenides due to their good nucleophilicity in aprotic solvents. 1 The following intermediates have been reported: ArSeZnCl, 1 ArSeCu, 2 ArSeSmI 2 , 3 Cp 2 TiSeAr, 4 Cp 2 Zr(SeMe) 2 , 5 Cp 2 Hf(SeMe) 2 , 5 and Cp 2 ZrSe 2 C 6 H 4 -o 6 and they have complemented in reactivity the known main group metal selenolates, such as Ar-SeNa, 7 Me 2 AlSeMe, 8 ArSeTl. 9 Vinylic selenolates are important intermediates for vinylic selenides, whose promising potential could be anticipated by the combination of the special reactivity of selenium and particularly reactivity associated with the carbon-carbon double bond.…”

A novel reduction of diketones with i-RMgBr catalyzed by Cp2TiCl2 and deoxygenation of sulfoxides by Cp2TiCl2/Al system

“…However, this method is not applicable to aromatic and α, β-unsaturated ketones. It was also reported that the Cp 2 TiCl 2 -catalyzed hydromagnesiation reaction of alkynes had recently become widely used in organic synthesis (Sato and Kobayashi, 1990;Gao and Sato, 1995;Xu and Huang, 1997). We described the Cp 2 TiCl 2 -catalyzed reduction of imines, isocyanates and β-diketones by Grignard reagents (Zhang and Hu, 1988;Zhang et al, 1987;Yu and Zhang, 1999).…”

Rongalite®/PEG-400 as reducing system in the synthesis of new glycerol-derived selenol esters using anhydrides and bis-(2,2-dimethyl-1,3-dioxolanylmethyl)diselenide as substrates

“…[11][12][13][14] They were also used as a precursors in the synthesis of vinyl compounds, 15 in the formation of C-peptide bonds, [16][17][18] and the synthesis of some natural occurring compounds, [19][20][21][22][23] besides having proven antioxidant properties. 24 Various methods have been described for the synthesis of selenol esters, for example, by the condensation of selenolate anions 25 or radicals 26 with carbonyl compounds, such as aldehydes, 27,28 anhydrides 26,29-34 acyl chlorides [29][30][31][32][33][34] or starting from chalcogen acetylenes 35 and aryl iodides. 36 Generally, these methods have limitations related to metal-catalyzed synthesis, 37 high temperatures and volatile solvents 29 and long reaction times.…”