On water preparation of phenylselenoesters

Santi, Claudio; Battistelli, Benedetta; Testaferri, Lorenzo; Tiecco, Marcello

doi:10.1039/c2gc16541d

Cited by 61 publications

(39 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[1][2][3][4] In all the cases the on water conditions showed a rate acceleration when compared with the same reaction effected in THF. sterical hindrance on the reaction rate indicates that a SN2 mechanism is involved.…”

mentioning

confidence: 89%

“…Based on DFT calculations it has been suggested that the stereoconvergence is due to the interaction of the zinc atom that can be coordinated by the carbonyl group driving the nucleophilic attack to the formation of the Z-isomer. Recently, PhSeZnCl (1a) and PhSeZnBr (1b) were successfully used in on water condition for the synthesis of selenoesters starting from the acid chlorides 4 ( In the case of Michael addition to aldehydes, ketones and esters the reactivity of 1a appeared to be dependent on the nature of the substrate. 3 When the unsaturation is a double bond, the best results were obtained in THF whereas, moving to the electrondeficient alkynes, the on-water rate acceleration was demonstrated, indicating that the solvent probably acts in the activation of the substrate rather than the zinc selenolate complex.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Highlight on the reactivity of PhSeZnX

Monti

Sancineto

Palomba

et al. 2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

Self Cite

View full text Add to dashboard Cite

Abstract:The first bench stable selenolates, PhSeZnHalides have been synthesized through a completely atom-economic oxidative insertion of the elemental zinc on the commercially available PhSeHalides. These reagents showed the characteristic nucleophilic reactivity which will be reviewed in this report. All of the reactions were strongly accelerated when effected in water suspension. Alkyl, aryl, vinyl and acyl substitutions, ring-opening reactions of epoxides and aziridines and Michael type addition will be described including the role of the zinc in the control of the chemoselectivity and stereoselectivity.

show abstract

mentioning

confidence: 89%

mentioning

confidence: 99%

Highlight on the reactivity of PhSeZnX

Monti

Sancineto

Palomba

et al. 2015

Proceedings of the 19th International Electronic Conference on Synthetic Organic Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…[18][19][20] Particularly interesting is the substitution of acyl chlorides that in water showed an unexpected prevalence of the selenation reaction over the most expectable hydrolysis.…”

Section: Figure 4: Synthesis Of Santi's Reagentsmentioning

confidence: 99%

Organoselenium Chemistry: after 200 years the "Gold Rush" is still open

Santi

Marini

Bagnoli

et al. 2017

Proceedings of the 21st International Electronic Conference on Synthetic Organic Chemistry

Self Cite

View full text Add to dashboard Cite

This manuscript aims to be a celebrative tribute to the 200 th anniversary of "selenium birthday" presenting an overview of the contribute of our group in different fields of this research, ranging from the development of new reagents for green chemistry and catalysis to the design and synthesis of novel molecules as anti-HIV and, as recently reported by others, antimicrobial agents. We are strongly convinced that in the next future important discoveries could emerge as a result of a research that produces thousands of new publications every year. In the form of prospective article here we just collect selected results among those presented by our young students at 6 th Workshop of the SeSRedCat Network which was held in Wroclaw, Poland (21 th 23 rd September 2017) Selenium (Se) was named by J. J. Berzelius exactly 200 years ago after its discovery in the residue of sulfuric acid preparations from a mining operation. At the beginning Berzelius believed to have in his hands a sample of Tellurium (discovered some years before) and only at the beginning of 1818 further investigations on the redox properties demonstrated that it was a new element and the name Selenium

show abstract

“…(E) Very recently, Santi et al 6 have proposed a greener method to synthesize selenoesters by the reaction of phenylselenyl zinc halides with acyl chlorides in 'on water' conditions; the products are obtained in moderate to good yield after crystallization from ethyl acetate-hexane and the aqueous medium can be reused.…”

Section: Preparationmentioning

confidence: 99%