Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums
This manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rin...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2023-12, Vol.365 (24), p.4576-4582 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Garay‐Talero, Alexander Acosta‐Guzmán, Paola Gamba‐Sánchez, Diego |
| description | This manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rings. Additionally, the utilization of chlorosulfonium salts as the chlorinating agent is demonstrated. The method emerges as an alternative to other processes where organic byproducts must be separated from the reaction mixture. In addition, the main byproducts are gaseous materials such as CO and CO2. This publication introduces the application of sulfoxides, oxalyl chloride, and aqueous hydrogen peroxide as the chlorination mixture. |
| doi_str_mv | 10.1002/adsc.202300971 |
| format | Article |
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It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rings. Additionally, the utilization of chlorosulfonium salts as the chlorinating agent is demonstrated. The method emerges as an alternative to other processes where organic byproducts must be separated from the reaction mixture. In addition, the main byproducts are gaseous materials such as CO and CO2. 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This publication introduces the application of sulfoxides, oxalyl chloride, and aqueous hydrogen peroxide as the chlorination mixture.</description><subject>Amines</subject><subject>Arenes</subject><subject>Aromatic compounds</subject><subject>Aryl halides</subject><subject>Byproducts</subject><subject>Carboxylic acids</subject><subject>Chlorination</subject><subject>Electrophilic substitution</subject><subject>Functional groups</subject><subject>Halogenation</subject><subject>Hydrogen peroxide</subject><subject>Mixtures</subject><subject>Organic Catalysis</subject><subject>Reagents</subject><subject>Regioselectivity</subject><subject>Sulfur</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkMtLw0AQxhdRsFavngOeU_eR7GaPJdYHVAo-jrJsN5N2S5qtu4kl_vUmVOrRwzDzwfebGT6ErgmeEIzprS6CmVBMGcZSkBM0IpykcUK4PD3OKT5HFyFsMCYiE2KEPl5gZV2ACkxjvyBa-JWundGNrrpvKKJn16t15bytdWNdHbkymnqoIUR726yj2QB6t1vbypooH5wutFXpattuwyU6K3UV4Oq3j9H7_ewtf4zni4enfDqPDRWUxIRjDmmptemLS5xQzCVAkYgkKzmTLAVcJDxdpplITMaYKUyv6ZItJWGGsjG6OezdeffZQmjUxrW-7k8qKjETjPKE9K7JwWX6H4OHUu283WrfKYLVEKEaIlTHCHtAHoC9raD7x62md6_5H_sDIKp2-w</recordid><startdate>20231219</startdate><enddate>20231219</enddate><creator>Garay‐Talero, Alexander</creator><creator>Acosta‐Guzmán, Paola</creator><creator>Gamba‐Sánchez, Diego</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-5432-5108</orcidid></search><sort><creationdate>20231219</creationdate><title>Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums</title><author>Garay‐Talero, Alexander ; Acosta‐Guzmán, Paola ; Gamba‐Sánchez, Diego</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2721-1606e5faacfaa69042069eed4748f63935e0d465b5874c833cdcd462b3b913c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Amines</topic><topic>Arenes</topic><topic>Aromatic compounds</topic><topic>Aryl halides</topic><topic>Byproducts</topic><topic>Carboxylic acids</topic><topic>Chlorination</topic><topic>Electrophilic substitution</topic><topic>Functional groups</topic><topic>Halogenation</topic><topic>Hydrogen peroxide</topic><topic>Mixtures</topic><topic>Organic Catalysis</topic><topic>Reagents</topic><topic>Regioselectivity</topic><topic>Sulfur</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Garay‐Talero, Alexander</creatorcontrib><creatorcontrib>Acosta‐Guzmán, Paola</creatorcontrib><creatorcontrib>Gamba‐Sánchez, Diego</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Garay‐Talero, Alexander</au><au>Acosta‐Guzmán, Paola</au><au>Gamba‐Sánchez, Diego</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-12-19</date><risdate>2023</risdate><volume>365</volume><issue>24</issue><spage>4576</spage><epage>4582</epage><pages>4576-4582</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>This manuscript presents a regioselective chlorination of arenes, yielding almost exclusively the monochlorinated product. It tolerates free hydroxy groups, 1°, 2° and 3° amines, and carboxylic acids, among other polar and nonpolar functional groups, as well as mono‐ and polysubstituted aromatic rings. Additionally, the utilization of chlorosulfonium salts as the chlorinating agent is demonstrated. The method emerges as an alternative to other processes where organic byproducts must be separated from the reaction mixture. In addition, the main byproducts are gaseous materials such as CO and CO2. This publication introduces the application of sulfoxides, oxalyl chloride, and aqueous hydrogen peroxide as the chlorination mixture.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202300971</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-5432-5108</orcidid></addata></record> |
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| subjects | Amines Arenes Aromatic compounds Aryl halides Byproducts Carboxylic acids Chlorination Electrophilic substitution Functional groups Halogenation Hydrogen peroxide Mixtures Organic Catalysis Reagents Regioselectivity Sulfur |
| title | Regioselective Organocatalyzed Monochlorination of Arenes with Electrophilic Chlorosulfoniums |
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