Selenium as a Versatile Reagent in Organic Synthesis: More than Allylic Oxidation

Abstract

: For many years since its discovery, Selenium has played the role of a bad boy who became a hero in organic transformations. Selenium dioxide, for instance, is one of the most remembered reagents in allylic oxidations, having been applied in the synthesis of several naturally occurring products. The main goal of this review is to show the recent advances in the use of classical and new selenium reagents in organic synthesis. As demonstrated through around 60 references discussed in this study, selenium can go even forward as a versatile reagent. We bring a collection of selenium reagents and their transformations that are still hidden from most synthetic organic chemists.

ROS-Scavenging Selenofluoxetine Derivatives Inhibit In Vivo Serotonin Reuptake

“…The choice of the chalcogen is based on the well-known antioxidant role selenium plays in biology, as a constituent of the catalytic residue of enzymes like glutathione peroxidase (GPx) and thioredoxin reductase (TrxR) . Importantly, the synthesis of organoselenides as GPx mimics is still considered an active research task and is worldwide pursued by an active community. − …”

A Golden Synthetic Approach to 2-(1H-Pyrrol-1-yl)anilines and Pyrrolo[1,2-a]quinoxalines through a Gold Carbene Intermediate

“…As a result, we tested various oxidants for the cyclization of pyrrole 4a (Table 2 ) and SeO 2 was found to be the best oxidant for converting the methyl group into aldehyde (entries 4), a process known as the Riley oxidation. 15c , 17` b c d The other oxidants, such as CAN 18a (Table 2 , entry 2) and KMnO 4 18b (entry 3) did not give any cyclic product.…”

Selenium dioxide as a selenylating reagent: An overview and its Sanguine future

“…He has four years of experience in teaching undergraduate and postgraduate courses. He holds master's is added to the pre-stirred mixture of selenium dioxide and malononitrile gave the selenocyanated product, while the addition of selenium dioxide to the pre stirred mixture of N,Ndimethyl aniline and malononitrile gave the selenocyanate (8b), di(p-dimethylaminophenyl) selenide (11), di(p-dimethylaminophenyl)malononitrile (12) and a small amount of 4-(1,2,2-tricyanovinyl)dimethylaniline (13). To confirm the mechanism, some controlled reaction carried out between selenium dioxide and malononitrile for 10 min at room temperature in DMSO.…”

“…It mainly acts as an oxidizing agent, dehydrating agent, reductive carbonylation, and oxidative demethylating agent [10] . There are many research group, that discussed the different domains of selenium [11] but selenium dioxide is much more than an allylic oxidizing agent, and its applications as a reagent and selenylating agent is not much elaborated.…”