Recent advances in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides
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This review summarizes the latest achievements in photochemical and electrochemical strategies for the synthesis of sulfonyl fluorides and focuses on the novel features and proposed mechanisms.Keywords:
Sulfonyl
Abstract Sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides as readily available and efficient sulfonylation reagents have been extensively explored in recent years. Sulfonyl radical can be generated from these sulfonyl reagents via different methods, then the sulfonyl radical could react with various substrates via different pathways to afford the corresponding products. In this review, we will summarize the progress in sulfonylation via radical reaction using sodium sulfinates, sulfinic acids, sulfonyl chlorides and sulfonyl hydrazides in recent three years. In terms of the different sulfonylation reagents, we classify these sulfonylation reactions into four types: 1. Sulfonylation reaction using sodium sulfinates. 2. Sulfonylation reaction using sulfinic acid. 3. Sulfonylation reaction using sulfonyl chlorides. 4. Sulfonylation reaction using sulfonyl hydrazides.
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Sulfonyl azides have been widely used as sulfonamido, diazo, and azido donors, as well as all-nitrogen 1,3-dipoles donors in synthetic chemistry. Here, the sulfonyl azides were used as efficient sulfonyl donors, which is very unusual. Trifluoromethanesulfonic acid-induced formation of the sulfonyl cation reactive species from sulfonyl azides was developed and used for the first time to couple various inactivated arenes to prepare sulfones at ambient temperature.
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Sulfonyl migrations, frequently described as ‘unusual’ or ‘unexpected’, from the last 20 years, including 1,2-, 1,3-, 1,4-, 1,5-, 1,6- and 1,7-sulfonyl shifts, through either radical or polar processes, either inter- or intramolecularly are reviewed.
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A strategy for the rapid synthesis of 3‐substituted N ‐sulfonyl pyrazoles via p ‐TSA‐promoted cyclization reactions of sulfonyl hydrazines with N , N ‐dimethyl enaminones has been developed. This method achieves both the formation of pyrazole ring and the continued retention of sulfonyl group, providing a series of 3‐substituted N ‐sulfonyl pyrazoles in moderate to good yields with good functional group tolerance, easily available starting materials, and can be scaled‐up.
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A visible-light photoredox-catalyzed sulfonyl lactonization of unsaturated carboxylic acids with sulfonyl chlorides is described. This reaction features good functional group tolerance and a broad substrate scope, providing a simple and efficient protocol to access a wide range of sulfonyl lactones in high to excellent yields. Preliminary mechanistic investigations suggested that a free-radical pathway should be involved in the process.
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