Palladium-catalyzed aerobic (1+2) annulation of Csp3-H bonds with olefin for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene
A novel palladium-catalyzed aerobic (1+2) annulation was developed for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene. The palladation of Csp3-H bonds took place twice at the same position in the whole reaction process. Preliminary mechanistic studies by in situ IR revealed that the second C-H pallad...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2017-02, Vol.53 (14), p.2294-2297 |
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creator | Wu, Kun Meng, Lingkui Huai, Mingming Huang, Zhiliang Liu, Chao Qi, Xiaotian Lei, Aiwen |
description | A novel palladium-catalyzed aerobic (1+2) annulation was developed for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene. The palladation of Csp3-H bonds took place twice at the same position in the whole reaction process. Preliminary mechanistic studies by in situ IR revealed that the second C-H palladation and reductive elimination might be slow steps. |
doi_str_mv | 10.1039/c6cc09332a |
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Preliminary mechanistic studies by in situ IR revealed that the second C-H palladation and reductive elimination might be slow steps.</description><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Olefins</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Synthesis</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqNkMFKAzEYhIMoWKsXnyDHiqQm-ZNtcpRirVDQQw-CSPk3m9CVbVKbXbR9erfoAziXmcPHwAwh14KPBQd75wrnuAWQeEIGAgrFtDKvp8esLZuA0ufkIucP3ktoMyCHF2warOpuwxy22OwPvqLod6msHR2JW3lDMcauwbZOkaZAp3kLbE7LFKtMv-p2TVPjQx1pSDvarj3N-9hbrvORBoYH7Kv2rklvMBZj_r7230wyH_0lOQvYZH_150OynD0sp3O2eH58mt4v2LYoLPNlKKX1VvNK8RC4Vkq5ytmJMVgZJdEGVyJABSgDOINc2wKD5aXvD5EFDMnot3a7S5-dz-1qU2fn-9XRpy6vhDFKSGEn9h9ooTVILgT8ALisbVo</recordid><startdate>20170214</startdate><enddate>20170214</enddate><creator>Wu, Kun</creator><creator>Meng, Lingkui</creator><creator>Huai, Mingming</creator><creator>Huang, Zhiliang</creator><creator>Liu, Chao</creator><creator>Qi, Xiaotian</creator><creator>Lei, Aiwen</creator><scope>7X8</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20170214</creationdate><title>Palladium-catalyzed aerobic (1+2) annulation of Csp3-H bonds with olefin for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene</title><author>Wu, Kun ; Meng, Lingkui ; Huai, Mingming ; Huang, Zhiliang ; Liu, Chao ; Qi, Xiaotian ; Lei, Aiwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p669-ebfb29e950d40ff05444cdc9788ad842a9fcba33d3a2f3c8a0596af90be039263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Olefins</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Kun</creatorcontrib><creatorcontrib>Meng, Lingkui</creatorcontrib><creatorcontrib>Huai, Mingming</creatorcontrib><creatorcontrib>Huang, Zhiliang</creatorcontrib><creatorcontrib>Liu, Chao</creatorcontrib><creatorcontrib>Qi, Xiaotian</creatorcontrib><creatorcontrib>Lei, Aiwen</creatorcontrib><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Kun</au><au>Meng, Lingkui</au><au>Huai, Mingming</au><au>Huang, Zhiliang</au><au>Liu, Chao</au><au>Qi, Xiaotian</au><au>Lei, Aiwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-catalyzed aerobic (1+2) annulation of Csp3-H bonds with olefin for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2017-02-14</date><risdate>2017</risdate><volume>53</volume><issue>14</issue><spage>2294</spage><epage>2297</epage><pages>2294-2297</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A novel palladium-catalyzed aerobic (1+2) annulation was developed for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene. The palladation of Csp3-H bonds took place twice at the same position in the whole reaction process. Preliminary mechanistic studies by in situ IR revealed that the second C-H palladation and reductive elimination might be slow steps.</abstract><doi>10.1039/c6cc09332a</doi><tpages>4</tpages></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Chemical bonds Chemical reactions Olefins Organic chemistry Palladium Synthesis |
title | Palladium-catalyzed aerobic (1+2) annulation of Csp3-H bonds with olefin for the synthesis of 3-azabicyclo[3.1.0]hex-2-ene |
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