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1.
Org Biomol Chem ; 22(13): 2492-2509, 2024 Mar 27.
Artigo em Inglês | MEDLINE | ID: mdl-38446020

RESUMO

Direct vicinal difunctionalization of π-systems has emerged as a powerful platform for constructing multiple bonds in a single synthetic operation using simple chemical feedstocks. Over the past decade, there has been exponential growth in the direct construction of successive C-S and C-I bonds using a wide variety of sulfonyl and iodide reactants through 1,2-iodosulfonylation of alkynes in a regio- and stereo-selective manner. In this review, we mainly focus on the recent developments in the preparation of ß-iodovinyl sulfones and their practical applications in organic synthesis. The most promising photoredox and electrochemical transformations for synthesizing ß-iodovinyl sulfones are also reviewed. The multifunctional ß-iodovinyl sulfones have recently been burgeoning as versatile synthetic precursors due to the combination of vinyl iodide and vinyl sulfone moieties, essential building blocks for diverse synthetic manipulations. We hereby present the chemistry of ß-iodovinyl sulfones, which can be classified into numerous sections based on the sulfonyl surrogates, and potential synthetic approaches are systematically outlined.

2.
Org Biomol Chem ; 19(14): 3087-3118, 2021 04 14.
Artigo em Inglês | MEDLINE | ID: mdl-33885563

RESUMO

This review mainly focuses on recent developments in the preparation of ß-keto sulfones and their extensive synthetic applications. New prospects for the synthesis of ß-keto thiosulfones have also been highlighted. Over the last decade, there has been exponential growth in the direct construction of ß-keto sulfones using a wide variety of keto and sulfonyl precursors. Of note, the most promising photoredox transformations and electrochemical synthesis methods of ß-keto sulfones are also presented. Moreover, ß-keto sulfones are versatile building blocks in organic synthesis due to their three essential functional groups: sulfonyl, carbonyl, and active methylene moieties. The convenient preparation of ß-keto sulfones allows the synthesis of many valuable carbocyclic and heterocyclic compounds, and the effortless removal of the sulfonyl moiety via transformations is supported. The chemistry of ß-keto sulfones (2013 to present) can be divided into several sections based on the sulfonyl surrogates, and ubiquitous synthetic strategies were systematically outlined.

3.
RSC Adv ; 8(70): 40446-40453, 2018 Nov 28.
Artigo em Inglês | MEDLINE | ID: mdl-35558195

RESUMO

A practical, highly flexible and eco-friendly method has been developed for the synthesis of allyl thiosulfonates using Morita-Baylis-Hillman (MBH) allyl bromides and sodium arylthiosulfonates, which were readily assembled without any reagent/catalyst. Moreover, the allyl thiosulfonates were successfully transformed into a set of two synthetically viable diallyl disulfanes and unsymmetrical allyl disulfanes in the presence of Cs2CO3. The present protocols are operationally simple and convenient to generate a wide range of functionalized allyl thiosulfonates and allyl disulfanes in good to excellent yields.

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