Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N‐Fluorobenzenesulfonimide as an Oxidant
A transition‐metal‐free electrophilic bromination and iodination of arene through C−H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment‐benign and readily available sodium halides, NaBr or NaI, w...
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creator | Shi, Cuiying Miao, Qi Ma, Lifang Lu, Tao Yang, Dong Chen, Jiaming Li, Ziyuan |
description | A transition‐metal‐free electrophilic bromination and iodination of arene through C−H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment‐benign and readily available sodium halides, NaBr or NaI, were employed as halogen sources in accompany with N‐fluorobenzenesulfonimide (NFSI) as an oxidant. Studies have also demonstrated that, in this air‐ and moisture‐resistant scalable halogenation under mild conditions, the oxidant NFSI is reduced to dibenzenesulfonimide which usually serves as the starting material for the preparation of NFSI, rendering this facile and versatile protocol promising potentials for future applications in organic synthesis.
A novel metal‐free oxidative C−H bromination and iodination of arene in excellent yields at room temperature with broad arene scope and gratifying generality, employing NaBr/NaI and NFSI as the halogen source and oxidant, respectively |
doi_str_mv | 10.1002/slct.201901456 |
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A novel metal‐free oxidative C−H bromination and iodination of arene in excellent yields at room temperature with broad arene scope and gratifying generality, employing NaBr/NaI and NFSI as the halogen source and oxidant, respectively</description><identifier>ISSN: 2365-6549</identifier><identifier>EISSN: 2365-6549</identifier><identifier>DOI: 10.1002/slct.201901456</identifier><language>eng</language><subject>Bromination ; Iodination ; N-Fluorobenzenesulfonimide ; Sodium Bromide ; Sodium Iodide</subject><ispartof>ChemistrySelect (Weinheim), 2019-05, Vol.4 (20), p.6043-6047</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2896-23d5f10366f5bfccbc39bde143b445705d065a93b0aab4ef64ea61b4167811823</citedby><cites>FETCH-LOGICAL-c2896-23d5f10366f5bfccbc39bde143b445705d065a93b0aab4ef64ea61b4167811823</cites><orcidid>0000-0001-8029-9804</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%2Fslct.201901456$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fslct.201901456$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Shi, Cuiying</creatorcontrib><creatorcontrib>Miao, Qi</creatorcontrib><creatorcontrib>Ma, Lifang</creatorcontrib><creatorcontrib>Lu, Tao</creatorcontrib><creatorcontrib>Yang, Dong</creatorcontrib><creatorcontrib>Chen, Jiaming</creatorcontrib><creatorcontrib>Li, Ziyuan</creatorcontrib><title>Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N‐Fluorobenzenesulfonimide as an Oxidant</title><title>ChemistrySelect (Weinheim)</title><description>A transition‐metal‐free electrophilic bromination and iodination of arene through C−H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment‐benign and readily available sodium halides, NaBr or NaI, were employed as halogen sources in accompany with N‐fluorobenzenesulfonimide (NFSI) as an oxidant. Studies have also demonstrated that, in this air‐ and moisture‐resistant scalable halogenation under mild conditions, the oxidant NFSI is reduced to dibenzenesulfonimide which usually serves as the starting material for the preparation of NFSI, rendering this facile and versatile protocol promising potentials for future applications in organic synthesis.
A novel metal‐free oxidative C−H bromination and iodination of arene in excellent yields at room temperature with broad arene scope and gratifying generality, employing NaBr/NaI and NFSI as the halogen source and oxidant, respectively</description><subject>Bromination</subject><subject>Iodination</subject><subject>N-Fluorobenzenesulfonimide</subject><subject>Sodium Bromide</subject><subject>Sodium Iodide</subject><issn>2365-6549</issn><issn>2365-6549</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkLtOwzAYhS0EElXpypwXSPG9yQgRhUoVlWg7R3Zig1FiV3aiUiZmJp6RJyEl5bIx_f85Ot8ZDgDnCI4RhPgiVEUzxhClEFHGj8AAE85izmh6_Oc_BaMQniCEiCccs8kAvN07V3-8vq9UvVFeNK1XUdbp2-jKu9pY0RhnI2HLaObKb7k1zWO07HRb97FSfUUO1j7ZOetg7EN015VNq9Z5J5V9UVaFttLOmh4KHRctnk0pbHMGTrSoghod7hCsp9er7DaeL25m2eU8LnCS8hiTkmkECeeaSV0UsiCpLBWiRFLKJpCVkDOREgmFkFRpTpXgSFLEJwlCCSZDMO57C-9C8ErnG29q4Xc5gvl-zHw_Zv4zZgekPbA1ldr9k86X82z1y34Coe9-TQ</recordid><startdate>20190531</startdate><enddate>20190531</enddate><creator>Shi, Cuiying</creator><creator>Miao, Qi</creator><creator>Ma, Lifang</creator><creator>Lu, Tao</creator><creator>Yang, Dong</creator><creator>Chen, Jiaming</creator><creator>Li, Ziyuan</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-8029-9804</orcidid></search><sort><creationdate>20190531</creationdate><title>Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N‐Fluorobenzenesulfonimide as an Oxidant</title><author>Shi, Cuiying ; Miao, Qi ; Ma, Lifang ; Lu, Tao ; Yang, Dong ; Chen, Jiaming ; Li, Ziyuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2896-23d5f10366f5bfccbc39bde143b445705d065a93b0aab4ef64ea61b4167811823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Bromination</topic><topic>Iodination</topic><topic>N-Fluorobenzenesulfonimide</topic><topic>Sodium Bromide</topic><topic>Sodium Iodide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shi, Cuiying</creatorcontrib><creatorcontrib>Miao, Qi</creatorcontrib><creatorcontrib>Ma, Lifang</creatorcontrib><creatorcontrib>Lu, Tao</creatorcontrib><creatorcontrib>Yang, Dong</creatorcontrib><creatorcontrib>Chen, Jiaming</creatorcontrib><creatorcontrib>Li, Ziyuan</creatorcontrib><collection>CrossRef</collection><jtitle>ChemistrySelect (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shi, Cuiying</au><au>Miao, Qi</au><au>Ma, Lifang</au><au>Lu, Tao</au><au>Yang, Dong</au><au>Chen, Jiaming</au><au>Li, Ziyuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N‐Fluorobenzenesulfonimide as an Oxidant</atitle><jtitle>ChemistrySelect (Weinheim)</jtitle><date>2019-05-31</date><risdate>2019</risdate><volume>4</volume><issue>20</issue><spage>6043</spage><epage>6047</epage><pages>6043-6047</pages><issn>2365-6549</issn><eissn>2365-6549</eissn><abstract>A transition‐metal‐free electrophilic bromination and iodination of arene through C−H cleavage at room temperature has been developed in excellent to quantitative yields with broad arene scope and good regioselectivity, in which environment‐benign and readily available sodium halides, NaBr or NaI, were employed as halogen sources in accompany with N‐fluorobenzenesulfonimide (NFSI) as an oxidant. Studies have also demonstrated that, in this air‐ and moisture‐resistant scalable halogenation under mild conditions, the oxidant NFSI is reduced to dibenzenesulfonimide which usually serves as the starting material for the preparation of NFSI, rendering this facile and versatile protocol promising potentials for future applications in organic synthesis.
A novel metal‐free oxidative C−H bromination and iodination of arene in excellent yields at room temperature with broad arene scope and gratifying generality, employing NaBr/NaI and NFSI as the halogen source and oxidant, respectively</abstract><doi>10.1002/slct.201901456</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8029-9804</orcidid></addata></record> |
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subjects | Bromination Iodination N-Fluorobenzenesulfonimide Sodium Bromide Sodium Iodide |
title | Room‐Temperature C‐H Bromination and Iodination with Sodium Bromide and Sodium Iodide Using N‐Fluorobenzenesulfonimide as an Oxidant |
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