{"created":"2021-03-01T06:00:48.012432+00:00","id":8448,"links":{},"metadata":{"_buckets":{"deposit":"0da526e0-8910-4d34-afd4-3789a6eb5aa0"},"_deposit":{"id":"8448","owners":[],"pid":{"revision_id":0,"type":"depid","value":"8448"},"status":"published"},"_oai":{"id":"oai:kitami-it.repo.nii.ac.jp:00008448","sets":["1:86"]},"author_link":["44871","44488","44489","44490","44491"],"item_1646810750418":{"attribute_name":"出版タイプ","attribute_value_mlt":[{"subitem_version_resource":"http://purl.org/coar/version/c_ab4af688f83e57aa","subitem_version_type":"AM"}]},"item_3_biblio_info_186":{"attribute_name":"書誌情報","attribute_value_mlt":[{"bibliographicIssueDates":{"bibliographicIssueDate":"2008","bibliographicIssueDateType":"Issued"},"bibliographicPageEnd":"3600","bibliographicPageStart":"3591","bibliographicVolumeNumber":"22","bibliographic_titles":[{"bibliographic_title":"Synthesis"}]}]},"item_3_description_184":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Described herein is an operationally simple and mild method for the stereospecific synthesis of internal conjugated (Z)-enynyltrimethylsilanes whose conjugation is extended away from the distal alkynyl carbon atom. This protocol involves two types of cross-coupling reaction, a Suzuki-type reaction and a sila-Sonogashira reaction, and the desired synthesis can be performed in a one-pot manner. Thus, the copper-mediated cross-coupling reaction of dicyclohexyl[(Z)-1-(trimethylsilyl)alk-1-enyl]boranes with (trimethylsilyl)ethynyl bromide is carried out in the presence of aqueous lithium hydroxide at -15 ?C to room temperature, resulting in the stereospecific formation of (Z)-1,3-bis(trimethylsilyl)alk-3-en-1-ynes. Subsequent reaction is allowed to proceed without isolation of the enynes. Thus, palladium/copper-catalyzed cross-coupling reactions with aryl iodides, cycloalk-1-enyl triflates, and (E)- and (Z)-alk-1-enyl iodides can be accomplished in the presence of either 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or tetrabutylammonium fluoride (TBAF) at ambient temperature to provide the corresponding internal conjugated (Z)-enynyltrimethylsilanes possessing one more sp-sp2 carbon bond.","subitem_description_type":"Abstract"}]},"item_3_full_name_183":{"attribute_name":"著者別名","attribute_value_mlt":[{"nameIdentifiers":[{"nameIdentifier":"44871","nameIdentifierScheme":"WEKO"},{"nameIdentifier":"113712","nameIdentifierScheme":"KAKEN","nameIdentifierURI":"https://nrid.nii.ac.jp/ja/nrid/1000000113712 "}],"names":[{"name":"星, 雅之","nameLang":"ja"}]}]},"item_3_publisher_212":{"attribute_name":"出版者","attribute_value_mlt":[{"subitem_publisher":"Georg Thieme Verlag"}]},"item_3_relation_191":{"attribute_name":"DOI","attribute_value_mlt":[{"subitem_relation_type_id":{"subitem_relation_type_id_text":"http://doi.org/10.1055/s-0028-1083201","subitem_relation_type_select":"DOI"}}]},"item_3_rights_192":{"attribute_name":"権利","attribute_value_mlt":[{"subitem_rights":"c Georg Thieme Verlag Stuttgart ? New York"}]},"item_3_select_195":{"attribute_name":"著者版フラグ","attribute_value_mlt":[{"subitem_select_item":"author"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"open access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_abf2"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Hoshi, Masayuki","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"44488","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Iizawa, Tomohiko","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"44489","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Okimoto, Mitsuhiro","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"44490","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Shirakawa, Kazuya","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"44491","nameIdentifierScheme":"WEKO"}]}]},"item_files":{"attribute_name":"ファイル情報","attribute_type":"file","attribute_value_mlt":[{"accessrole":"open_date","date":[{"dateType":"Available","dateValue":"2017-01-12"}],"displaytype":"detail","filename":"f16208ss.pdf","filesize":[{"value":"230.2 kB"}],"format":"application/pdf","licensetype":"license_note","mimetype":"application/pdf","url":{"label":"f16208ss.pdf","url":"https://kitami-it.repo.nii.ac.jp/record/8448/files/f16208ss.pdf"},"version_id":"038ea7ee-f6ec-4c5e-9583-9472e9011772"}]},"item_keyword":{"attribute_name":"キーワード","attribute_value_mlt":[{"subitem_subject":"(Z)-enynyltrimethylsilane","subitem_subject_scheme":"Other"},{"subitem_subject":"(trimethylsilyl)ethynyl bromide","subitem_subject_scheme":"Other"},{"subitem_subject":"(Z)-1,3-bis(trimethylsilyl)alk-3-en-1-yne","subitem_subject_scheme":"Other"},{"subitem_subject":"Suzuki-type reaction","subitem_subject_scheme":"Other"},{"subitem_subject":"sila-Sonogashira reaction","subitem_subject_scheme":"Other"}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"journal article","resourceuri":"http://purl.org/coar/resource_type/c_6501"}]},"item_title":"One-pot synthesis of internal conjugated (Z)-enynyltrimethylsilanes possessing aryl, cycloalkenyl, (E)- or (Z)-alk-1-enyl moieties on the sp carbon atom via two types of cross-coupling reaction","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"One-pot synthesis of internal conjugated (Z)-enynyltrimethylsilanes possessing aryl, cycloalkenyl, (E)- or (Z)-alk-1-enyl moieties on the sp carbon atom via two types of cross-coupling reaction","subitem_title_language":"en"}]},"item_type_id":"3","owner":"1","path":["86"],"pubdate":{"attribute_name":"PubDate","attribute_value":"2016-08-31"},"publish_date":"2016-08-31","publish_status":"0","recid":"8448","relation_version_is_last":true,"title":["One-pot synthesis of internal conjugated (Z)-enynyltrimethylsilanes possessing aryl, cycloalkenyl, (E)- or (Z)-alk-1-enyl moieties on the sp carbon atom via two types of cross-coupling reaction"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2022-12-13T02:22:48.201815+00:00"}