Stereospecific Synthesis of (Z,Z)‐Isobenzofurans via Radical‐Enabled Cleavage of C(sp3)−C(sp3) and C(sp2)‐Halogen Bonds
A novel radical‐induced annulation/1,8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)−C(sp3) and C(sp2)‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethy...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-12, Vol.361 (23), p.5340-5345 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Huang, Min‐Hua Shi, Hao‐Nan Zhu, Chi‐Fan He, Chun‐Lan Hao, Wen‐Juan Tu, Shu‐Jiang Jiang, Bo |
| description | A novel radical‐induced annulation/1,8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)−C(sp3) and C(sp2)‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethylene‐substituted (Z,Z)‐isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in‐situ generation of arylsulfonyl radicals, followed by selective radical addition‐cyclization and ring‐opening of the cyclopropyl unit as well as C(sp2)‐halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C−S, C−O and C‐halogen bonds. |
| doi_str_mv | 10.1002/adsc.201900729 |
| format | Article |
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This multicomponent pathway is proposed to proceed through the in‐situ generation of arylsulfonyl radicals, followed by selective radical addition‐cyclization and ring‐opening of the cyclopropyl unit as well as C(sp2)‐halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C−S, C−O and C‐halogen bonds.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201900729</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>1,3-dimethylene-substituted (Z,Z)-isobenzofurans ; 1,8-halosulfonylation ; Annulation ; Chemical bonds ; Chemical reactions ; Cleavage ; Cleavage/recombination ; Ketones ; Organic chemistry ; Organic compounds ; Sulfur dioxide ; β-alkynyl ketones</subject><ispartof>Advanced synthesis & catalysis, 2019-12, Vol.361 (23), p.5340-5345</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3549-68725900467f3e2a411a72654f013c26db5b7a96dc0ebf943c0c5e524e5bb8e93</citedby><cites>FETCH-LOGICAL-c3549-68725900467f3e2a411a72654f013c26db5b7a96dc0ebf943c0c5e524e5bb8e93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201900729$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201900729$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,782,786,1419,27931,27932,45581,45582</link.rule.ids></links><search><creatorcontrib>Huang, Min‐Hua</creatorcontrib><creatorcontrib>Shi, Hao‐Nan</creatorcontrib><creatorcontrib>Zhu, Chi‐Fan</creatorcontrib><creatorcontrib>He, Chun‐Lan</creatorcontrib><creatorcontrib>Hao, Wen‐Juan</creatorcontrib><creatorcontrib>Tu, Shu‐Jiang</creatorcontrib><creatorcontrib>Jiang, Bo</creatorcontrib><title>Stereospecific Synthesis of (Z,Z)‐Isobenzofurans via Radical‐Enabled Cleavage of C(sp3)−C(sp3) and C(sp2)‐Halogen Bonds</title><title>Advanced synthesis & catalysis</title><description>A novel radical‐induced annulation/1,8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)−C(sp3) and C(sp2)‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethylene‐substituted (Z,Z)‐isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in‐situ generation of arylsulfonyl radicals, followed by selective radical addition‐cyclization and ring‐opening of the cyclopropyl unit as well as C(sp2)‐halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C−S, C−O and C‐halogen bonds.</description><subject>1,3-dimethylene-substituted (Z,Z)-isobenzofurans</subject><subject>1,8-halosulfonylation</subject><subject>Annulation</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>Cleavage/recombination</subject><subject>Ketones</subject><subject>Organic chemistry</subject><subject>Organic compounds</subject><subject>Sulfur dioxide</subject><subject>β-alkynyl ketones</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAQhS0EEqWwMltiaSVSbCeOm7GEQitVQqKwdLEc51JShTjEbVFZYGRE_MT-EhKCysh0T3fvu9M9hE4p6VFC2IWKre4xQgNCBAv2UIv6lDse9YP9nebkEB1ZuyCEir4QLfQ2XUIJxhag0yTVeLrJl49gU4tNgjuz81l3-_45tiaC_NUkq1LlFq9The9UnGqVVcNhrqIMYhxmoNZqDjUYdmzhdrcfX43AKo9_eqzeNlKZmUOOL00e22N0kKjMwslvbaOH6-F9OHImtzfjcDBxtMu9wPH7gvHqMc8XiQtMeZQqwXzuJYS6mvlxxCOhAj_WBKIk8FxNNAfOPOBR1IfAbaOzZm9RmucV2KVcmFWZVyclcxlljBPOK1evcenSWFtCIosyfVLlRlIi65BlHbLchVwBQQO8pBls_nHLwdU0_GO_AaqbgqU</recordid><startdate>20191203</startdate><enddate>20191203</enddate><creator>Huang, Min‐Hua</creator><creator>Shi, Hao‐Nan</creator><creator>Zhu, Chi‐Fan</creator><creator>He, Chun‐Lan</creator><creator>Hao, Wen‐Juan</creator><creator>Tu, Shu‐Jiang</creator><creator>Jiang, Bo</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20191203</creationdate><title>Stereospecific Synthesis of (Z,Z)‐Isobenzofurans via Radical‐Enabled Cleavage of C(sp3)−C(sp3) and C(sp2)‐Halogen Bonds</title><author>Huang, Min‐Hua ; Shi, Hao‐Nan ; Zhu, Chi‐Fan ; He, Chun‐Lan ; Hao, Wen‐Juan ; Tu, Shu‐Jiang ; Jiang, Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3549-68725900467f3e2a411a72654f013c26db5b7a96dc0ebf943c0c5e524e5bb8e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>1,3-dimethylene-substituted (Z,Z)-isobenzofurans</topic><topic>1,8-halosulfonylation</topic><topic>Annulation</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>Cleavage/recombination</topic><topic>Ketones</topic><topic>Organic chemistry</topic><topic>Organic compounds</topic><topic>Sulfur dioxide</topic><topic>β-alkynyl ketones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Min‐Hua</creatorcontrib><creatorcontrib>Shi, Hao‐Nan</creatorcontrib><creatorcontrib>Zhu, Chi‐Fan</creatorcontrib><creatorcontrib>He, Chun‐Lan</creatorcontrib><creatorcontrib>Hao, Wen‐Juan</creatorcontrib><creatorcontrib>Tu, Shu‐Jiang</creatorcontrib><creatorcontrib>Jiang, Bo</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>Huang, Min‐Hua</au><au>Shi, Hao‐Nan</au><au>Zhu, Chi‐Fan</au><au>He, Chun‐Lan</au><au>Hao, Wen‐Juan</au><au>Tu, Shu‐Jiang</au><au>Jiang, Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereospecific Synthesis of (Z,Z)‐Isobenzofurans via Radical‐Enabled Cleavage of C(sp3)−C(sp3) and C(sp2)‐Halogen Bonds</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-12-03</date><risdate>2019</risdate><volume>361</volume><issue>23</issue><spage>5340</spage><epage>5345</epage><pages>5340-5345</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A novel radical‐induced annulation/1,8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO.bis(sulfur dioxide) was first achieved via the cleavage/recombination of C(sp3)−C(sp3) and C(sp2)‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethylene‐substituted (Z,Z)‐isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in‐situ generation of arylsulfonyl radicals, followed by selective radical addition‐cyclization and ring‐opening of the cyclopropyl unit as well as C(sp2)‐halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C−S, C−O and C‐halogen bonds.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201900729</doi><tpages>6</tpages></addata></record> |
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| subjects | 1,3-dimethylene-substituted (Z,Z)-isobenzofurans 1,8-halosulfonylation Annulation Chemical bonds Chemical reactions Cleavage Cleavage/recombination Ketones Organic chemistry Organic compounds Sulfur dioxide β-alkynyl ketones |
| title | Stereospecific Synthesis of (Z,Z)‐Isobenzofurans via Radical‐Enabled Cleavage of C(sp3)−C(sp3) and C(sp2)‐Halogen Bonds |
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