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      Inorganic sulfites as the sulfur dioxide surrogates in sulfonylation reactions

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          Abstract

          Recent advances in the sulfonylation reactions by using inorganic sulfites as the source of sulfonyl group are reported. The approaches employing inorganic sulfites as the sulfur dioxide surrogates are attractive and promising for the synthesis of sulfonyl compounds since inorganic sulfites are abundant, easily available and cheap.

          Abstract

          Recent advances in the sulfonylation reactions by using inorganic sulfites as the source of sulfonyl group are reported. The approaches employing inorganic sulfites as sulfur dioxide surrogates are attractive and promising for the synthesis of sulfonyl compounds since inorganic sulfites are abundant, easily available and cheap. The transformations using inorganic sulfites as the source of sulfonyl group work efficiently, providing diverse sulfonyl compounds including sulfones and sulfonamides. The sulfonylation reactions can be performed under transition metal catalysis or through radical processes under catalyst- and additive-free conditions. In some cases, a photocatalyst is employed under visible-light irradiation to facilitate the transformation. For the sulfur dioxide surrogate of inorganic sulfites, potassium metabisulfite or sodium metabisulfite has been broadly used in various transformations. However, the reactivities of inorganic sulfites in organic reactions still need to be explored.

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          Drug Discovery: A Historical Perspective

          J. Drews (2000)
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            Palladium-catalyzed C-H bond functionalization with arylsulfonyl chlorides.

            Selective C-H bond functionalization enables efficient access to valuable products from relatively simple precursors and thus remains a longstanding challenge in organic synthesis. This communication highlights the discovery of arylsulfonyl chlorides as readily available, inexpensive, and versatile reagents for C-H bond functionalization. A novel Pd-catalyzed synthesis of arylsulfones that features a rare C-H bond activation/functionalization to form a C-S bond is presented. By simple alterations of the reaction parameters, Pd-catalyzed C-Cl and C-C bond formation can also be achieved using arylsulfonyl chlorides as the oxidant.
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              Palladium-catalyzed aminosulfonylation of aryl halides.

              The palladium-catalyzed three-component coupling of aryl iodides, sulfur dioxide, and hydrazines to deliver aryl N-aminosulfonamides is described. The colorless crystalline solid DABCO·(SO(2))(2) was used as a convenient source of sulfur dioxide. The reaction tolerates significant variation of both the aryl iodide and hydrazine coupling partners.
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                Author and article information

                Contributors
                Journal
                CHCOFS
                Chemical Communications
                Chem. Commun.
                Royal Society of Chemistry (RSC)
                1359-7345
                1364-548X
                January 22 2019
                2019
                : 55
                : 8
                : 1013-1019
                Affiliations
                [1 ]School of Pharmaceutical and Chemical Engineering
                [2 ]Taizhou University
                [3 ]Taizhou 318000
                [4 ]China
                [5 ]College of Biological
                [6 ]Chemical Science and Engineering
                [7 ]Jiaxing University
                [8 ]Jiaxing 314001
                [9 ]Department of Chemistry
                Article
                10.1039/C8CC09250H
                4c1e8797-e7e8-49f9-a068-8b7c1523bf89
                © 2019

                http://rsc.li/journals-terms-of-use

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