Direct Synthesis of Thioethers from Carboxylates and Thiols Catalyzed by FeCl₃

Abstract

A new and efficient method has been developed for the synthesis of thioethers from carboxylates and thiols. The reaction proceeds via a Fe(III)-catalyzed direct displacement of carboxylates from benzylic or allylic esters by heterocyclic thiols. Short reaction times, good to excellent yields of products, and few side reactions are the significant features of the new protocol.

Gold-catalyzed thioetherification of allyl, benzyl, and propargyl phosphates

“…Activation of C(sp 3 )–O bonds by Lewis acid catalysts has been reported to be one of the most effective methods for the efficient thioetherification of C(sp 3 )–O bonds. In this regard, Fe, 13,14 Ni, 15 Ru, 16–20 Pd, 21–30 In, 31,32 Ir, 33–35 Au, 36 and lanthanoides 37 have all been reported to be efficient catalysts for thioetherification of C(sp 3 )–O bonds. On the other hand, supported metal nanoparticle (NP) catalysts have attracted considerable attention since they facilitate the recycling of precious metals and reduce contamination of products from metallic loads.…”

Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate

“…Thioethers are important and useful compounds as they have a broad range of biological activities The key fragments of many important pharmacophores are S ‐benzylated moieties of thioethers , . There are several synthetic methods for the alkylation of thiols such as classical ones that include substitution reactions of the corresponding halides,, sulfonates, and carboxylates , . It is the good leaving group ability of these functionalities that make them so useful in organic chemistry (Figure ).…”