Synthetic Approaches to Selenoesters

Abstract

Selenoesters are compounds of great synthetic relevance since they can be used in several types of chemical transformations and mainly due to their great capacity in the formation of acyl radicals. Therefore, the scientific community has been developing several methods for the synthesis of this class of molecules. This review will address the synthesis of these compounds from different starting materials, such as carboxylic acids derivatives (acid chlorides and anhydrides), aldehydes, selenoacetylenes and miscellaneous methods.

Ru‐catalyzed Formation of Thiosilanes and Selenosilanes using Dichalcogenides as a User‐Friendly Alternative to Thiols and Selenols

“…[34] Furthermore, the synthesis of organoselenium compounds has gained recent significant attention, especially due to the fact of their interesting, and somewhat unique properties and applications. [34][35][36][37][38][39][40] We were pleased to find that diphenyldiselenide was successfully silylated/germylated under standard conditions (Scheme 3), leading to products 7 a and 7 b in very good yields (86-88 %).…”

Selenourea as a hydrogen bond donor catalyst and source of selenium for metal-, activator-free synthesis of selenoesters in a batch and flow reactor

“…The selenoesters are synthesized from acyl chlorides, aldehydes, anhydrides, selenoacetylenes, and carboxylic acids. 34,35 Most of the methods involve conversion of carboxylic acids to acyl halides, and followed by catalysis by metals like Pd, 35 Sn/Cu, 35 indium, 36 iron, 37 lanthanum, 38 samarium, 39 mercury, 40 Zn, 41 and rhodium. 42 Acyl halides are highly moisture sensitive and difficult to handle.…”

Transition‐Metal Free, One Pot Synthesis of Selenoesters via Reaction of Alkyl Selenides and Acyl Chlorides

“…Considering the biological relevance of selenoesters and applications in material science, traditionally, several approaches have been developed for their synthesis [16] . Usually, this class of compounds were prepared by the reaction of acyl chlorides or anhydrides with aryl‐selenolate anion generated in situ from the reductive cleavage of diorganyl diselenides (Scheme 1a).…”