Recent Advances in the Synthesis of Selenophenes and Their Derivatives

Abstract

The selenophene derivatives are an important class of selenium-based heterocyclics. These compounds play an important role in prospecting new drugs, as well as in the development of new light-emitting materials. During the last years, several methods have been emerging to access the selenophene scaffold, employing a diversity of cyclization-based synthetic strategies, involving specific reaction partners and particularities. This review presents a comprehensive discussion on the recent advances in the synthesis of selenophene-based compounds, starting from different precursors, highlighting the main differences, the advantages, and limitations among them.

PhICl2-Mediated Regioselective and Electrophilic Oxythio/Selenocyanation of o-(1-Alkynyl)benzoates: Access to Biologically Active S/SeCN-Containing Isocoumarins

“…Then the reaction of thiocyanate with thiocyanogen chloride provides (SCN) 2 , which further reacts with the oxidative PhICl 2 to give thiocyanogen chloride ( Tao et al, 2021 ). Next, electrophilic addition between the reactive thiocyanogen chloride with substrate 1a gave rise to intermediate B ( Xing et al, 2019a ; An et al, 2020 ; Hellwig et al, 2020 ; Lynch and Scanlan, 2020 ; Sun et al, 2020 ; Jurinic et al, 2021 ; Slivka and Onysko, 2021 ). Due to the presence of the adjacent electron-withdrawing methoxycarbonyl group which makes the C (sp 2 ) connecting with the Ph substituent more electron-deficient, a favored intramolecular 6-exo cyclization occurred in intermediate B , leading to formation of the cyclic intermediate C .…”

Hydroelementation of diynes

“…[422][423][424][425][426] These molecules can be prepared by various synthetic pathways however, the most frequently employed method for their preparation is the hydroselenation of the CRC bond by nucleophilic organoselenolate anions. The synthesis and application of organoselenium compounds, especially selenophenes, has been summarised in many books and reviews, 422,423,425,[427][428][429][430][431][432][433][434] nevertheless the hydroselenation of diynes have not been comprehensively reviewed.…”

Recent Advances in the Oxone-Mediated Synthesis of Heterocyclic Compounds

“…Chalcogenophenes are a valuable class of heterocyclic compounds, which play an important role as building blocks in organic synthesis [42], in the development of new materials [43,44], and in the prospection of new drugs in the pharmaceutical industry [45,46]. Due to these important features, the search for the development of simple and efficient methods to access chalcogenophenes has attracted interest during the last decades.…”