{"id":353,"date":"2022-08-30T20:33:51","date_gmt":"2022-08-30T11:33:51","guid":{"rendered":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/?p=353"},"modified":"2025-06-13T10:51:36","modified_gmt":"2025-06-13T01:51:36","slug":"annulative-coupling-of-vinylboronic-esters-aryne-triggered-12-metallate-rearrangement","status":"publish","type":"post","link":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/archives\/353","title":{"rendered":"Annulative coupling of vinylboronic esters: aryne-triggered 1,2-metallate rearrangement"},"content":{"rendered":"\n<div class=\"wp-block-group\"><div class=\"wp-block-group__inner-container is-layout-flow wp-block-group-is-layout-flow\">\n<p>Haruki Mizoguchi*, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida,\u00a0Akira Sakakura*<br><em>Chem. Sci.<\/em> <strong>2022<\/strong>, <em>13<\/em>, 9580\u20139585.<br>DOI: \/10.1039\/D2SC02623F<\/p>\n\n\n\n<p><\/p>\n<\/div><\/div>\n\n\n\n<figure class=\"wp-block-image size-full is-resized\"><img loading=\"lazy\" decoding=\"async\" src=\"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/WordPress\/wp-content\/uploads\/2022\/08\/GA.tiff\" alt=\"\" class=\"wp-image-354\" width=\"815\" height=\"208\"\/><\/figure>\n\n\n\n<p><\/p>\n\n\n\n<p>A stereoselective annulative coupling of a vinylboronic ester ate-complex with arynes producing cyclic borinic esters has been developed. An annulation reaction that proceeded through the formation of two C\u2013C bonds and a C\u2013B bond was realized by exploiting a 1,2-metallate rearrangement of boronate triggered by the addition of a vinyl group to the strained triple bond of an aryne. The generated aryl anion would then cyclize to a boron atom to complete the annulation cascade. The annulated borinic ester could be converted to boronic acids and their derivatives by oxidation, halogenation, and cross-coupling. Particularly, halogenation and Suzuki\u2013Miyaura coupling proceeded in a site-selective fashion and produced highly substituted alkylboronic acid derivatives.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Haruki Mizoguchi*, Hidetoshi Kamada, Kazuki Morimoto, Ryuji Yoshida,\u00a0Akira Sakakura*Chem. Sci. 2022, 13, 9580\u2013 [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":354,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"vkexunit_cta_each_option":"","footnotes":""},"categories":[4,6],"tags":[],"class_list":["post-353","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-news","category-publications"],"_links":{"self":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/353","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/comments?post=353"}],"version-history":[{"count":3,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/353\/revisions"}],"predecessor-version":[{"id":359,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/posts\/353\/revisions\/359"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media\/354"}],"wp:attachment":[{"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/media?parent=353"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/categories?post=353"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/achem.okayama-u.ac.jp\/bioorgchem\/wp-json\/wp\/v2\/tags?post=353"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}