Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins
A transition‐metal‐free difluoromethylenation of diazo compounds that proceeds under mild conditions has been developed and is based on the use of TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the promoter. The chemoselective formal carbene dimerization reaction i...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-01, Vol.55 (1), p.273-277 |
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| creator | Zhang, Zhikun Yu, Weizhi Wu, Chenggui Wang, Chengpeng Zhang, Yan Wang, Jianbo |
| description | A transition‐metal‐free difluoromethylenation of diazo compounds that proceeds under mild conditions has been developed and is based on the use of TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the promoter. The chemoselective formal carbene dimerization reaction is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.
Formal carbene dimerization: The difluoromethylenation of diazo compounds was achieved under mild conditions with TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the initiator. The chemoselective formal carbene dimerization is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate. |
| doi_str_mv | 10.1002/anie.201509711 |
| format | Article |
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Formal carbene dimerization: The difluoromethylenation of diazo compounds was achieved under mild conditions with TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the initiator. The chemoselective formal carbene dimerization is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201509711</identifier><identifier>PMID: 26768823</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>carbenes ; diazo compounds ; difluorocarbene ; Dimerization ; Electronic properties ; fluorine ; hydrazones ; Tetrabutylammonium bromide</subject><ispartof>Angewandte Chemie International Edition, 2016-01, Vol.55 (1), p.273-277</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5461-1cb6d0d5d76da6d69a4cfce232af6dfcdcf0009c34287c5befe50f2f6f1828423</citedby><cites>FETCH-LOGICAL-c5461-1cb6d0d5d76da6d69a4cfce232af6dfcdcf0009c34287c5befe50f2f6f1828423</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%2Fanie.201509711$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201509711$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26768823$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Zhikun</creatorcontrib><creatorcontrib>Yu, Weizhi</creatorcontrib><creatorcontrib>Wu, Chenggui</creatorcontrib><creatorcontrib>Wang, Chengpeng</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><title>Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A transition‐metal‐free difluoromethylenation of diazo compounds that proceeds under mild conditions has been developed and is based on the use of TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the promoter. The chemoselective formal carbene dimerization reaction is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.
Formal carbene dimerization: The difluoromethylenation of diazo compounds was achieved under mild conditions with TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the initiator. The chemoselective formal carbene dimerization is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.</description><subject>carbenes</subject><subject>diazo compounds</subject><subject>difluorocarbene</subject><subject>Dimerization</subject><subject>Electronic properties</subject><subject>fluorine</subject><subject>hydrazones</subject><subject>Tetrabutylammonium bromide</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkUtPGzEURi3UCmjabZfVSN2wYIIf48d0F4XwUCmV0iKWluOHMJ3YwZ5RCr--jgJR1UXZ2JZ1zqer-wHwEcExghCfqODtGENEYcsR2gOHiGJUE87Jm_JuCKm5oOgAvMv5vvBCQLYPDjDjTAhMDoGeW6V7H0MVXXXq1VOspnG5ikMwuVr7_q58um6IKWqVFjbYL9UkVDPnvPY29NVktUpR6buqj2uVioOOUf2ixM46H_J78NapLtsPz_cI3JzNfk4v6qvv55fTyVWtacNQjfSCGWio4cwoZlirGu20xQQrx4zTRjsIYatJgwXXdGGdpdBhxxwSWDSYjMDRNreM9DDY3Mulz9p2nQo2DlkizqAQ5WAF_fwPeh-HFMp0ErVYENwQ2PyX4pRDTjZLHIHxltIp5pysk6vklyo9SgTlpiS5KUnuSirCp-fYYbG0Zoe_tFKAdgusfWcfX4mTk-vL2d_h9db1ube_d65KvyTjhFN5e30u5xfkB_l2OpdfyR9I_6yZ</recordid><startdate>20160104</startdate><enddate>20160104</enddate><creator>Zhang, Zhikun</creator><creator>Yu, Weizhi</creator><creator>Wu, Chenggui</creator><creator>Wang, Chengpeng</creator><creator>Zhang, Yan</creator><creator>Wang, Jianbo</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160104</creationdate><title>Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins</title><author>Zhang, Zhikun ; Yu, Weizhi ; Wu, Chenggui ; Wang, Chengpeng ; Zhang, Yan ; Wang, Jianbo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5461-1cb6d0d5d76da6d69a4cfce232af6dfcdcf0009c34287c5befe50f2f6f1828423</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>carbenes</topic><topic>diazo compounds</topic><topic>difluorocarbene</topic><topic>Dimerization</topic><topic>Electronic properties</topic><topic>fluorine</topic><topic>hydrazones</topic><topic>Tetrabutylammonium bromide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhikun</creatorcontrib><creatorcontrib>Yu, Weizhi</creatorcontrib><creatorcontrib>Wu, Chenggui</creatorcontrib><creatorcontrib>Wang, Chengpeng</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zhikun</au><au>Yu, Weizhi</au><au>Wu, Chenggui</au><au>Wang, Chengpeng</au><au>Zhang, Yan</au><au>Wang, Jianbo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-01-04</date><risdate>2016</risdate><volume>55</volume><issue>1</issue><spage>273</spage><epage>277</epage><pages>273-277</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A transition‐metal‐free difluoromethylenation of diazo compounds that proceeds under mild conditions has been developed and is based on the use of TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the promoter. The chemoselective formal carbene dimerization reaction is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.
Formal carbene dimerization: The difluoromethylenation of diazo compounds was achieved under mild conditions with TMSCF2Br as the difluoromethylene source and tetrabutylammonium bromide (TBAB) as the initiator. The chemoselective formal carbene dimerization is achieved owing to the electronic properties and the relative stability of the difluorocarbene intermediate.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26768823</pmid><doi>10.1002/anie.201509711</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | carbenes diazo compounds difluorocarbene Dimerization Electronic properties fluorine hydrazones Tetrabutylammonium bromide |
| title | Reaction of Diazo Compounds with Difluorocarbene: An Efficient Approach towards 1,1-Difluoroolefins |
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