Insights into the Recent Synthetic Advances of Organoselenium Compounds

Abstract

The ever-growing interest for organoselenium compounds amongst the chemists has made commendable impact in the field of medicinal chemistry, material chemistry, chemical biology and biochemistry. Researchers have progressively contributed in the development of organoselenium compounds over the years which has been periodically reviewed. On the similar note, this review attempts at providing an overview of the recent advances made in organoselenium chemistry while covering their catalytic indulgence in different transformational approaches, their role in asymmetric synthesis, and synthetic approaches steering their synthesis. These approaches encompass selenofunctionalization and/or cyclization, electrochemical selenylation, bromolactonization, [2,3]-or [1,2]-sigmatropic rearrangement reactions among others. Herein, we have focused on the synthetic approaches developed for the past three years that have not been covered in previously reviewed scientific material. With the knowledge of the recent progress covered, this review could contribute towards future development of organoselenium compounds along with the improvement of the current status.

The First Selenoanhydride in the Series of Chlorophyll a Derivatives, Its Stability and Photoinduced Cytotoxicity

“…The possibility of synthesizing cyclic selenoanhydrides from derivatives of various dicarboxylic acids, including aliphatic, aromatic, and heterocyclic ones, was reported by a few researchers [ 23 , 24 , 25 , 26 ]. The synthesis of cyclic chlorin thioanhydride p 6 ( 2 ) was first performed by our team [ 50 ].…”

“…Selenophene is the simplest heterocyclic compound containing a selenium atom [ 23 , 24 ]. Several inorganic compounds are used as selenating agents in organic synthesis, including phosphorus pentaselenide, selenium oxides, and hydrogen selenide, which cause the cyclization of linear organic molecules to give selenophenes and their derivatives [ 24 , 25 , 26 ]. The latter are used as efficient antioxidants and extracting agents for the isolation and separation of metals, while some of them have high biological activity or find use as polymeric materials (tetra-substituted selenophene derivatives) [ 27 , 28 , 29 ].…”

Novel Organoselenium Redox Modulators with Potential Anticancer, Antimicrobial, and Antioxidant Activities

“…Furthermore, the function of various redox enzymes such as glutathione peroxidase (GPx), thioredoxin reductases, and iodothyronine deiodinases depends on the Se redox center [ 6 , 7 ]. Generally, organoselenium (OSe) compounds are less toxic than inorganic Se compounds [ 5 , 8 , 9 ]. The former compounds have recently gained significant attention due to their potential pharmacological properties [ 8 , 9 , 10 ].…”

“…Generally, organoselenium (OSe) compounds are less toxic than inorganic Se compounds [ 5 , 8 , 9 ]. The former compounds have recently gained significant attention due to their potential pharmacological properties [ 8 , 9 , 10 ].…”

TBHP‐Mediated Selenocyclization of N‐Allylbenzamides/Benzthioamides via In‐Situ Generation of “PhSeOH” Species**

“…The catalytic hallmark of organoselenium compounds is attributed to their redox properties and pronounced carbophilicity, which has been implied in numerous synthetic transformations. [14] One of these transformations involves a basic and important strategy of isohypsic or oxidative functionalization of simple unactivated alkenes (olefin functionalization), pioneered in the late 1970s, to develop functionalized hetero-or carbocyclic scaffolds economically. [15][16][17][18][19] Olefin functionalization credits mainly from their electrophilic and radical [20] facets.…”