Ruthenium-Catalyzed C−C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons
2H‐azirines can serve as three‐atom synthons by C−C bond cleavage, however, it involves a high energy barrier under thermal conditions (>50.0 kcal mol−1). Reported is a ruthenium‐catalyzed [3+2+2] cycloaddition reaction of 2H‐azirines with diynes, thus leading to the formation of fused azepine sk...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-02, Vol.55 (8), p.2861-2865 |
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| creator | Li, Tengfei Xu, Fen Li, Xincheng Wang, Chunxiang Wan, Boshun |
| description | 2H‐azirines can serve as three‐atom synthons by C−C bond cleavage, however, it involves a high energy barrier under thermal conditions (>50.0 kcal mol−1). Reported is a ruthenium‐catalyzed [3+2+2] cycloaddition reaction of 2H‐azirines with diynes, thus leading to the formation of fused azepine skeletons. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and the challenging construction of aza‐seven‐membered rings from diynes. The results of this study provide a new reaction pattern for constructing nitrogen‐containing seven‐membered rings and may find applications in the synthesis of other complex heterocycles.
Fusion rings: The ruthenium‐catalyzed [3+2+2] cycloaddition of 2H‐azirines with diynes has been established. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and achieves the challenging construction of aza‐seven‐membered rings from diynes. |
| doi_str_mv | 10.1002/anie.201510820 |
| format | Article |
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Fusion rings: The ruthenium‐catalyzed [3+2+2] cycloaddition of 2H‐azirines with diynes has been established. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and achieves the challenging construction of aza‐seven‐membered rings from diynes.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201510820</identifier><identifier>PMID: 26800151</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>alkynes ; Cleavage ; Construction ; Cycloaddition ; C−C activation ; heterocycles ; Ruthenium ; Temperature effects</subject><ispartof>Angewandte Chemie International Edition, 2016-02, Vol.55 (8), p.2861-2865</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></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.201510820$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201510820$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26800151$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Tengfei</creatorcontrib><creatorcontrib>Xu, Fen</creatorcontrib><creatorcontrib>Li, Xincheng</creatorcontrib><creatorcontrib>Wang, Chunxiang</creatorcontrib><creatorcontrib>Wan, Boshun</creatorcontrib><title>Ruthenium-Catalyzed C−C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>2H‐azirines can serve as three‐atom synthons by C−C bond cleavage, however, it involves a high energy barrier under thermal conditions (>50.0 kcal mol−1). Reported is a ruthenium‐catalyzed [3+2+2] cycloaddition reaction of 2H‐azirines with diynes, thus leading to the formation of fused azepine skeletons. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and the challenging construction of aza‐seven‐membered rings from diynes. The results of this study provide a new reaction pattern for constructing nitrogen‐containing seven‐membered rings and may find applications in the synthesis of other complex heterocycles.
Fusion rings: The ruthenium‐catalyzed [3+2+2] cycloaddition of 2H‐azirines with diynes has been established. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and achieves the challenging construction of aza‐seven‐membered rings from diynes.</description><subject>alkynes</subject><subject>Cleavage</subject><subject>Construction</subject><subject>Cycloaddition</subject><subject>C−C activation</subject><subject>heterocycles</subject><subject>Ruthenium</subject><subject>Temperature effects</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kc1u1DAUhS0EoqWwZYkssUGqUvwT2wm7EHU6RdVQ_sQCIctJrovbJJ7GCTDzBF33EXkSPJoyCxZd-Vr3O8e-9yD0nJIjSgh7bXoHR4xQQUnGyAO0TwWjCVeKP4x1ynmiMkH30JMQLiOfZUQ-RntMZmSj2UfXH6fxB_Ru6pLSjKZdraHB5Z-b2xK_9X0sWzA_zQVgbzGbJ8XaDa6H8AYXeOaHzrT4Gz9kh-w7Lld1603TuNH5Ho8ez6YQvYo1LKMCf7qCFkbfh6fokTVtgGd35wH6Mjv-XM6Ts_cnp2VxllykIiNxBMOllSoVhErLaCoNoWAJZ9Q2wPOqlkxaUUFVV8QamyoC0ma1MionvGb8AL3a-i4Hfz1BGHXnQg1ta3rwU9BUSZEzxoWM6Mv_0Es_DX38naZ53KuSTIh7qejFFONk8-yLO2qqOmj0cnCdGVb638ojkG-BX66F1a5Pid4EqjeB6l2gulicHu9uUZtstS6M8HunNcOVloorob8uTnT24R05n6uZXvC_KxegUw</recordid><startdate>20160218</startdate><enddate>20160218</enddate><creator>Li, Tengfei</creator><creator>Xu, Fen</creator><creator>Li, Xincheng</creator><creator>Wang, Chunxiang</creator><creator>Wan, Boshun</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160218</creationdate><title>Ruthenium-Catalyzed C−C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons</title><author>Li, Tengfei ; Xu, Fen ; Li, Xincheng ; Wang, Chunxiang ; Wan, Boshun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g4580-37a36f6745016f2146a01ef0321fde39bc626f5bebcb0faf470e6f8c7a7903c23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>alkynes</topic><topic>Cleavage</topic><topic>Construction</topic><topic>Cycloaddition</topic><topic>C−C activation</topic><topic>heterocycles</topic><topic>Ruthenium</topic><topic>Temperature effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Tengfei</creatorcontrib><creatorcontrib>Xu, Fen</creatorcontrib><creatorcontrib>Li, Xincheng</creatorcontrib><creatorcontrib>Wang, Chunxiang</creatorcontrib><creatorcontrib>Wan, Boshun</creatorcontrib><collection>Istex</collection><collection>PubMed</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>Li, Tengfei</au><au>Xu, Fen</au><au>Li, Xincheng</au><au>Wang, Chunxiang</au><au>Wan, Boshun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium-Catalyzed C−C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-02-18</date><risdate>2016</risdate><volume>55</volume><issue>8</issue><spage>2861</spage><epage>2865</epage><pages>2861-2865</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>2H‐azirines can serve as three‐atom synthons by C−C bond cleavage, however, it involves a high energy barrier under thermal conditions (>50.0 kcal mol−1). Reported is a ruthenium‐catalyzed [3+2+2] cycloaddition reaction of 2H‐azirines with diynes, thus leading to the formation of fused azepine skeletons. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and the challenging construction of aza‐seven‐membered rings from diynes. The results of this study provide a new reaction pattern for constructing nitrogen‐containing seven‐membered rings and may find applications in the synthesis of other complex heterocycles.
Fusion rings: The ruthenium‐catalyzed [3+2+2] cycloaddition of 2H‐azirines with diynes has been established. This approach features an unprecedented metal‐catalyzed C−C bond cleavage of 2H‐azirines at room temperature, and achieves the challenging construction of aza‐seven‐membered rings from diynes.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26800151</pmid><doi>10.1002/anie.201510820</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | alkynes Cleavage Construction Cycloaddition C−C activation heterocycles Ruthenium Temperature effects |
| title | Ruthenium-Catalyzed C−C Bond Cleavage of 2H-Azirines: A Formal [3+2+2] Cycloaddition to Fused Azepine Skeletons |
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