Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (2)

Search Parameters:
Keywords = selenol esters

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
15 pages, 10008 KB  
Article
A Simple Zinc-Mediated Method for Selenium Addition to Michael Acceptors
by Francesca Giulia Nacca, Bonifacio Monti, Eder João Lenardão, Paul Evans and Claudio Santi
Molecules 2020, 25(9), 2018; https://doi.org/10.3390/molecules25092018 - 26 Apr 2020
Cited by 15 | Viewed by 5712
Abstract
In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of [...] Read more.
In this work, we focused our attention on seleno-Michael type reactions. These were performed using zinc-selenolates generated in situ from diphenyl diselenide 1, 1,2-bis(3-phenylpropyl)diselenide 30, and protected selenocystine 31 via an efficient biphasic Zn/HCl-based reducing system. Alkenes with a variety of electron-withdrawing groups were investigated in order to gauge the scope and limitations of the process. Results demonstrated that the addition to acyclic α,β-unsaturated ketones, aldehydes, esters amides, and acids was effectively achieved and that alkyl substituents at the reactive β-centre can be accommodated. Similarly, cyclic enones undergo efficient Se-addition and the corresponding adducts were isolated in moderate to good yield. Vinyl sulfones, α,β-unsaturated nitriles, and chalcones are not compatible with these reaction conditions. A recycling experiment demonstrated that the unreacted Zn/HCl reducing system can be effectively reused for seven reaction cycles (91% conversion yield at the 7° recycling rounds). Full article
(This article belongs to the Special Issue Organoselenium Reagents and Their Applications)
Show Figures

Graphical abstract

13 pages, 4079 KB  
Article
Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions
by Luca Sancineto, Jaqueline Pinto Vargas, Bonifacio Monti, Massimiliano Arca, Vito Lippolis, Gelson Perin, Eder Joao Lenardao and Claudio Santi
Molecules 2017, 22(6), 953; https://doi.org/10.3390/molecules22060953 - 8 Jun 2017
Cited by 17 | Viewed by 6441
Abstract
We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic [...] Read more.
We describe here an atom efficient procedure to prepare selenol esters in good to excellent yields by reacting [(PhSe)2Zn] or [(PhSe)2Zn]TMEDA with acyl chlorides under “on water” conditions. The method is applicable to a series of aromatic and aliphatic acyl chlorides and tolerates the presence of other functionalities in the starting material. Full article
Show Figures

Graphical abstract

Back to TopTop