Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides
Diaryl sulfides are a class of important synthetic chemical units. Herein, we report a new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chl...
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Veröffentlicht in: | European journal of organic chemistry 2023-03, Vol.26 (12), p.n/a |
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creator | Li, Bao Wang, Junrui Tu, Guangliang Ju, Guodong Zhou, Kehan Zhao, Yingsheng |
description | Diaryl sulfides are a class of important synthetic chemical units. Herein, we report a new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated, resulting in moderate to good yields of diaryl sulfides. The potential of the proposed method is validated by good yields obtained in gram scale reactions.
A new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram scale reactions showed a satisfactory performance, demonstrating the potential synthetic application of this method. |
doi_str_mv | 10.1002/ejoc.202201458 |
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A new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram scale reactions showed a satisfactory performance, demonstrating the potential synthetic application of this method.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202201458</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>anisoles ; benzenesulfonyl chlorides ; Chlorides ; C−H functionalization ; diaryl sulfides ; hemin ; Sulfides</subject><ispartof>European journal of organic chemistry, 2023-03, Vol.26 (12), p.n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-699913b976915f95be60dacee6bb3c33d0bcaa15a52e8822decdf44c7b680e6f3</citedby><cites>FETCH-LOGICAL-c3178-699913b976915f95be60dacee6bb3c33d0bcaa15a52e8822decdf44c7b680e6f3</cites><orcidid>0000-0001-6827-4743 ; 0000-0002-6142-7839</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202201458$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202201458$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Li, Bao</creatorcontrib><creatorcontrib>Wang, Junrui</creatorcontrib><creatorcontrib>Tu, Guangliang</creatorcontrib><creatorcontrib>Ju, Guodong</creatorcontrib><creatorcontrib>Zhou, Kehan</creatorcontrib><creatorcontrib>Zhao, Yingsheng</creatorcontrib><title>Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides</title><title>European journal of organic chemistry</title><description>Diaryl sulfides are a class of important synthetic chemical units. Herein, we report a new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated, resulting in moderate to good yields of diaryl sulfides. The potential of the proposed method is validated by good yields obtained in gram scale reactions.
A new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram scale reactions showed a satisfactory performance, demonstrating the potential synthetic application of this method.</description><subject>anisoles</subject><subject>benzenesulfonyl chlorides</subject><subject>Chlorides</subject><subject>C−H functionalization</subject><subject>diaryl sulfides</subject><subject>hemin</subject><subject>Sulfides</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAQhi0EEqWwMltiTjnbiROPqBQKqlSkFonNSpyL6iqNi50KdWNkRDxin4RURTAy_Td8393pJ-SSwYAB8GtcOjPgwDmwOMmOSI-BUhFIBcfdHIs4Ykq8nJKzEJYAoKRkPTIZ48o2u_fPJ-9WrsWS3lqPpqXD3cfXmM4X1tV5a11DbUPbBdLZtuki2EBd1bG539Z0tqkrW2I4JydVXge8-Mk-eb4bzYfjaDK9fxjeTCIjWJpFUinFRKFSqVhSqaRACWVuEGVRCCNECYXJc5bkCccs47xEU1ZxbNJCZoCyEn1yddi79u51g6HVS7fxTXdS8zTLUsaTWHXU4EAZ70LwWOm1t6vuYc1A7xvT-8b0b2OdoA7Cm61x-w-tR4_T4Z_7DX_-cYI</recordid><startdate>20230321</startdate><enddate>20230321</enddate><creator>Li, Bao</creator><creator>Wang, Junrui</creator><creator>Tu, Guangliang</creator><creator>Ju, Guodong</creator><creator>Zhou, Kehan</creator><creator>Zhao, Yingsheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-6827-4743</orcidid><orcidid>https://orcid.org/0000-0002-6142-7839</orcidid></search><sort><creationdate>20230321</creationdate><title>Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides</title><author>Li, Bao ; Wang, Junrui ; Tu, Guangliang ; Ju, Guodong ; Zhou, Kehan ; Zhao, Yingsheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-699913b976915f95be60dacee6bb3c33d0bcaa15a52e8822decdf44c7b680e6f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>anisoles</topic><topic>benzenesulfonyl chlorides</topic><topic>Chlorides</topic><topic>C−H functionalization</topic><topic>diaryl sulfides</topic><topic>hemin</topic><topic>Sulfides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Bao</creatorcontrib><creatorcontrib>Wang, Junrui</creatorcontrib><creatorcontrib>Tu, Guangliang</creatorcontrib><creatorcontrib>Ju, Guodong</creatorcontrib><creatorcontrib>Zhou, Kehan</creatorcontrib><creatorcontrib>Zhao, Yingsheng</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Bao</au><au>Wang, Junrui</au><au>Tu, Guangliang</au><au>Ju, Guodong</au><au>Zhou, Kehan</au><au>Zhao, Yingsheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides</atitle><jtitle>European journal of organic chemistry</jtitle><date>2023-03-21</date><risdate>2023</risdate><volume>26</volume><issue>12</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Diaryl sulfides are a class of important synthetic chemical units. Herein, we report a new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated, resulting in moderate to good yields of diaryl sulfides. The potential of the proposed method is validated by good yields obtained in gram scale reactions.
A new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram scale reactions showed a satisfactory performance, demonstrating the potential synthetic application of this method.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202201458</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-6827-4743</orcidid><orcidid>https://orcid.org/0000-0002-6142-7839</orcidid></addata></record> |
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subjects | anisoles benzenesulfonyl chlorides Chlorides C−H functionalization diaryl sulfides hemin Sulfides |
title | Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides |
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