Advances in Vinyl Sulfone Catalyzed Synthesis: Methods, Mechanisms and Perspectives

Abstract

Vinyl sulfones are conjugated systems composed of C=C and S=O, which are considered to be significant building blocks in organic synthesis and as coupling agents because they can serve as Michael acceptors as well as 2π‐partners in cycloaddition reactions. The attractive bioactivity and unique chemical properties of the vinyl sulfone skeleton have led to its extensive study in organic synthesis and pharmaceutical chemistry. However, a systematic and comprehensive review of the routes for the catalytic synthesis of vinyl sulfones have not been carried out so far. In this paper, the applications of vinyl sulfone structures in biomolecular and organic syntheses are briefly investigated, and the current methods for the synthesis of vinyl sulfone structures in recent years using different catalysts are systematically reviewed and analyzed. Finally, the future opportunities and challenges for the synthesis and application of vinyl sulfone compounds are discussed.

Photochemical Halogen-Bonding Promoted Synthesis of Vinyl Sulfones via Vinyl and Sulfonyl Radicals

“…V inyl sulfones are commonly versatile building blocks and privileged structural motifs in the area of organic synthesis and medicinal chemistry. 1 Remarkably, vinyl sulfones have been found to possess a wide range of biological activities, such as anticancer, antiparasitic, antimicrobial, antiviral, neuroprotective, and radioprotective. 2 In addition, several bioactive molecules, including Rigosertib (anticancer agent in phase III clinical trials), , WRR-483 (cysteine protease inhibitor), and Recilisib (radiation protection agent), contain the vinyl sulfone moiety (Figure 1).…”

“…As depicted in Scheme 2, vinyl bromides with both electrondonating and electron-withdrawing substituents attached to the phenyl ring, such as 4-methyl, 4-N, N-dimethyl, 4-trifluoromethoxy, 4-acetoxyl, 4-methoxy, 4-chloro, 4-ester, 4-nitro, 2-chloro, and 3-methoxy, were suitable for this protocol, giving the corresponding products (C2−C11) in 34−96% yields. Meanwhile, vinyl benzo[d] [1,3]dioxole (C12), vinyl naphthalene (C13), and heteroaryl ethylene (C14 and C15) were also acceptable for this transformation, providing the target compounds in moderate to excellent yields. Moreover, cinnamic ethylenes (C17−C19) were well tolerated in this reaction in terms of isolated yield (55−70%).…”

“…Vinyl sulfones are commonly versatile building blocks and privileged structural motifs in the area of organic synthesis and medicinal chemistry . Remarkably, vinyl sulfones have been found to possess a wide range of biological activities, such as anticancer, antiparasitic, antimicrobial, antiviral, neuroprotective, and radioprotective .…”