{"id":18370,"date":"2018-03-20T06:26:08","date_gmt":"2018-03-19T22:26:08","guid":{"rendered":"\/\/www.gsbet888.com\/?p=18370"},"modified":"2019-08-02T18:51:49","modified_gmt":"2019-08-02T10:51:49","slug":"%e5%ae%ab%e6%b5%a6-%e7%9f%b3%e5%b1%b1%e7%a1%bc%e9%85%b8%e5%8c%96-miyaura-ishiyama-borylation","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2018\/03\/%e5%ae%ab%e6%b5%a6-%e7%9f%b3%e5%b1%b1%e7%a1%bc%e9%85%b8%e5%8c%96-miyaura-ishiyama-borylation.html","title":{"rendered":"\u5bab\u6d66-\u77f3\u5c71\u787c\u9178\u5316 Miyaura-Ishiyama Borylation"},"content":{"rendered":"<h4>\u6982\u8981<\/h4>\n<p>\u7531\u82b3\u57fa\u6216\u70ef\u57fa\u5364\u5316\u7269\/\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4f5c\u4e3a\u5e95\u7269\u4e0e\u94af\u50ac\u5316\u5242\u5408\u6210\u6709\u673a\u787c\u9178\u5316\u5408\u7269\u7684\u65b9\u6cd5\u3002\u5e02\u552e\u7684\u9891\u54ea\u9187\u4e8c\u787c\u5316\u5408\u7269(PinB-BPin)\u5e38\u5e38\u4f5c\u4e3a\u787c\u6e90\u3002\u53e6\u4e00\u65b9\u9762\u4f7f\u7528H-BPin\u3001(HO)<sub>2<\/sub>B-B(OH)<sub>2<\/sub>\u4f5c\u4e3a\u787c\u6e90\u7684\u6761\u4ef6\u4e5f\u6709\u6240\u62a5\u9053\u3002<\/p>\n<p>\u8fd1\u5e74\u6765\uff0c\u968f\u7740\u94f1\u50ac\u5316\u5242\u7684\u5f00\u53d1\u5e94\u7528\uff0c\u4e0d\u901a\u8fc7\u5364\u7d20\uff0c\u76f4\u63a5\u7ecf\u7531C-H\u6d3b\u5316\u8fdb\u884c\u787c\u9178\u5316\u7684\u53cd\u5e94\u88ab\u5f00\u53d1\uff08Hartwig\u00b7Miyaura\u787c\u5316\uff09\u3002 \u8bf7\u53c2\u9605\u5173\u8054\u53cd\u5e94\u3002<\/p>\n<h4>\u5173\u8054\u53cd\u5e94<\/h4>\n<ul class=\"list\">\n<li><a href=\"https:\/\/en.wikipedia.org\/wiki\/Liebeskind\u2013Srogl_coupling\">Liebeskind-Srogl Cross Coupling<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/%e5%81%b6%e8%81%94%e5%8f%8d%e5%ba%94\/2015\/05\/%e4%ba%a4%e5%8f%89%e8%84%b1%e6%b0%a2%e5%81%b6%e8%81%94%e5%8f%8d%e5%ba%94cross-dehydrogenative-coupling-cdc.html\">Cross Dehydrogenative Coupling (CDC)<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/%e6%b0%a7%e5%8c%96%e5%8f%8d%e5%ba%94\/2015\/05\/c-h%e5%82%ac%e5%8c%96%e6%b0%a7%e5%8c%96%e5%8f%8d%e5%ba%94catalytic-c-h-oxidation.html\">Catalytic C-H Oxidation<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/%e8%87%aa%e7%94%b1%e5%9f%ba%e5%8f%8d%e5%ba%94\/2016\/09\/post-11095.html\">Hofmann-L\u00f6ffler-Freytag Reaction<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/%e6%9c%89%e6%9c%ba%e9%87%91%e5%b1%9e%e5%8f%8d%e5%ba%94-reactions\/2015\/05\/%e9%87%91%e5%b1%9e%e5%82%ac%e5%8c%96c-h%e6%b4%bb%e5%8c%96catalytic-c-h-activation.html\">Catalytic C-H activation<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/2014\/11\/%e9%87%91%e5%b1%9e%e5%8d%a1%e5%ae%be%e7%9a%84c-h%e6%8f%92%e5%85%a5%e5%8f%8d%e5%ba%94c-h-insertion-of-metal-carbenoid.html\">C-H Insertion of Metal Carbenoid<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/2014\/02\/brown%e7%a1%bc%e6%b0%a2%e5%8c%96-%e6%b0%a7%e5%8c%96%e5%8f%8d%e5%ba%94brown-hydroboration.html\">Brown Hydroboration<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/2013\/12\/post-8.html\">Suzuki-Miyaura Cross Coupling<\/a><\/li>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/2016\/02\/post-8577.html\">Hartwig-Miyaura C-H Borylation<\/a><\/li>\n<\/ul>\n<h4>\u57fa\u672c\u6587\u732e<\/h4>\n<ul>\n<li>Ishiyama, T.; Murata, M.; Miyaura, N. <em>J. Org. Chem.<\/em> <strong>1995<\/strong>,\u00a0<em>60<\/em>, 7508. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo00128a024\">10.1021\/jo00128a024<\/a><\/li>\n<li>Murata, M.; Watanabe, S.; Masuda, Y. <em>J. Org. Chem. <\/em><strong>1997<\/strong>,\u00a0<em>62<\/em>, 6458. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo970963p\">10.1021\/jo970963p<\/a><\/li>\n<li>Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. <em>J. Org. Chem.\u00a0<\/em><strong>2000<\/strong>, <em>65<\/em>, 164. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo991337q\">10.1021\/jo991337q<\/a><\/li>\n<li>Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. <em>J. Am. Chem.\u00a0Soc.<\/em> <strong>2002<\/strong>, <em>124<\/em>, 8001. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/ja0202255\">10.1021\/ja0202255<\/a><\/li>\n<\/ul>\n<p>&lt;review&gt;<\/p>\n<ul>\n<li>Ishiyama, T.; Miyaura, N. <em>Chem. Rec.<\/em> <strong>2004<\/strong>,\u00a0<em>3<\/em>, 271. DOI:\u00a0<a href=\"http:\/\/dx.doi.org\/10.1002\/tcr.10068\">10.1002\/tcr.10068<\/a><\/li>\n<li>Shimizu, M.; Hiyama, T. <em>Eur. J. Org. Chem. <\/em><strong>2013<\/strong>,\u00a0<em>36<\/em>, 8096. DOI: <a href=\"http:\/\/dx.doi.org\/10.1002\/ejoc.201300632\">10.1002\/ejoc.201300632<\/a><\/li>\n<li>Chow, W. K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong,\u00a0W. T.; Kwong, F. Y. <em>RSC Adv.<\/em> <strong>2013<\/strong>, <em>3<\/em>, 12518. DOI:<a href=\"http:\/\/dx.doi.org\/10.1039\/C3RA22905J\"> 10.1039\/C3RA22905J<\/a><\/li>\n<li>Shinokubo, H. <em>Proc. Jpn. Acad. Ser. B.<\/em> <strong>2014<\/strong>,\u00a0<em>90<\/em>, 1. doi:<a href=\"http:\/\/dx.doi.org\/10.2183\/pjab.90.1\">10.2183\/pjab.90.1<\/a><\/li>\n<\/ul>\n<h4>\u53cd\u5e94\u673a\u7406<\/h4>\n<p>\u57fa\u672c\u53cd\u5e94\u673a\u7406\u4e0e\u94af\u4ea4\u53c9\u5076\u8054\u76f8\u4f3c\u3002\u5177\u4f53\u8bf7\u53c2\u7167<a href=\"\/\/www.gsbet888.com\/reactions\/2013\/12\/post-8.html\">Suzuki-Miyaura Cross Coupling<\/a>\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-18372 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_2-680x434.png\" alt=\"\" width=\"440\" height=\"281\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_2-680x434.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_2-300x191.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_2.png 726w\" sizes=\"(max-width: 440px) 100vw, 440px\" \/><\/p>\n<h4>\u53cd\u5e94\u5b9e\u4f8b<\/h4>\n<p>\u901a\u8fc7\u9009\u62e9\u5177\u6709\u9002\u5f53\u53cd\u5e94\u6027\u7684\u5e95\u7269\uff0c\u53ef\u4ee5\u7ecf\u8fc7Miyaura\u787c\u9178\u5316\u2192Suzuki-Miyaura\u4ea4\u53c9\u5076\u8054\u7684\u8fde\u7eed\u53cd\u5e94\u83b7\u5f97\u8054\u82b3\u70c3\u3002<\/p>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-18373 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_5.gif\" alt=\"\" width=\"480\" height=\"147\" \/><\/p>\n<p>\u9002\u7528\u4e8e\u4f4e\u53cd\u5e94\u6027\u6c2f\u4ee3\u82b3\u70c3\u7684\u53cd\u5e94\u6761\u4ef6[1]\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-18374 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_3-680x230.png\" alt=\"\" width=\"526\" height=\"178\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_3-680x230.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_3-300x101.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_3-768x260.png 768w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_3.png 1008w\" sizes=\"(max-width: 526px) 100vw, 526px\" \/><\/p>\n<h4>\u5b9e\u9a8c\u6b65\u9aa4<\/h4>\n<p>\u82b3\u57fa\u6eb4\u5316\u7269\u7684\u787c\u5316[2]\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-18375 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_4-680x427.png\" alt=\"\" width=\"497\" height=\"312\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_4-680x427.png 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_4-300x188.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_4.png 727w\" sizes=\"(max-width: 497px) 100vw, 497px\" \/><\/p>\n<h4>\u5b9e\u9a8c\u6280\u5de7<\/h4>\n<p>\u203b\u78b1\u7684\u8bddKOAc\u662f\u6700\u4f18\u7684\u3002\u5728\u4f7f\u7528\u50cfK<sub>2<\/sub>CO<sub>3\uff0c<\/sub>K<sub>3<\/sub>PO<sub>4<\/sub>\u8fd9\u6837\u76f8\u5bf9\u5f3a\u7684\u78b1\u7684\u8bdd\uff0c\u4f1a\u4f34\u968f\u5f62\u6210\u94c3\u6728\u5076\u8054\u5f62\u5f0f\u7684\u4e8c\u805a\u4f53\u526f\u4ea7\u7269\u3002\u5bf9\u4e09\u6c1f\u7532\u78fa\u9178\u70ef\u57fa\u916f\u4f5c\u4e3a\u5e95\u7269\u7684\u65f6\u5019\uff0c\u4f7f\u7528KOPh\u505a\u4e3a\u78b1\u8fdb\u884c\u53cd\u5e94\u3002<br \/>\n\u203b\u5bf9\u4e8e\u6eb6\u5242\uff0c\u53cd\u5e94\u901f\u5ea6\u5982\u4e0b DMSO &gt;&gt; DMF &gt; 1,4-dioxane\u3002<\/p>\n<p>&nbsp;<\/p>\n<h4>\u53c2\u8003\u6587\u732e<\/h4>\n<ol>\n<li>(a) Billingsley, K. L.; Barder, T. E.; Buchwald, S. L.<em> Angew.\u00a0Chem. Int. Ed.<\/em> <strong>2007<\/strong>, <em>46<\/em>, 5359. doi:<a href=\"http:\/\/dx.doi.org\/10.1002\/anie.200701551\">10.1002\/anie.200701551<\/a>\u00a0(b) Billingsley, K. L.; Buchwald, S. L. <em>J. Org. Chem.<\/em> <strong>2008<\/strong>,\u00a0<em>73<\/em>, 5589. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo800727s\">10.1021\/jo800727s<\/a><\/li>\n<li>Ishiyama, T.; Murata, M.; Miyaura, N. <em>J. Org. Chem.<\/em> <strong>1995<\/strong>,\u00a0<em>60<\/em>, 7508. DOI: <a href=\"http:\/\/dx.doi.org\/10.1021\/jo00128a024\">10.1021\/jo00128a024<\/a><\/li>\n<\/ol>\n<p>\u672c\u6587\u7248\u6743\u5c5e\u4e8e<strong>\u00a0<a href=\"\/\/www.gsbet888.com\/\">Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c<\/strong> \u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01 <\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u7531\u82b3\u57fa\u6216\u70ef\u57fa\u5364\u5316\u7269\/\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4f5c\u4e3a\u5e95\u7269\u4e0e\u94af\u50ac\u5316\u5242\u5408\u6210\u6709\u673a\u787c\u9178\u5316\u5408\u7269\u7684\u65b9\u6cd5\u3002\u5e02\u552e\u7684\u9891\u54ea\u9187\u4e8c\u787c\u5316\u5408\u7269(PinB-BPin)\u5e38\u5e38\u4f5c\u4e3a\u787c\u6e90\u3002\u53e6\u4e00\u65b9\u9762\u4f7f\u7528H-BPin\u3001(HO)2B-B(OH)2\u4f5c\u4e3a\u787c\u6e90\u7684\u6761\u4ef6\u4e5f\u6709\u6240\u62a5\u9053\u3002 \u8fd1\u5e74\u6765\uff0c\u968f\u7740\u94f1\u50ac\u5316\u5242\u7684\u5f00\u53d1\u5e94\u7528\uff0c\u4e0d\u901a\u8fc7\u5364\u7d20\uff0c\u76f4\u63a5\u7ecf\u7531C-H\u6d3b\u5316\u8fdb\u884c\u787c\u9178\u5316\u7684\u53cd\u5e94\u88ab\u5f00\u53d1\uff08Hartwig\u00b7Miyaura\u787c\u5316\uff09\u3002 \u8bf7\u53c2\u9605\u5173\u8054\u53cd\u5e94\u3002 \u5173\u8054\u53cd\u5e94 Liebeskind-Srogl Cross Coupling Cross Dehydrogenative Coupling (CDC) Catalytic C-H Oxidation Hofmann-L\u00f6ffler-Freytag Reaction Catalytic C-H activation C-H Insertion of Metal Carbenoid Brown Hydroboration Suzuki-Miyaura Cross Coupling Hartwig-Miyaura C-H Borylation \u57fa\u672c\u6587\u732e Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995,\u00a060, 7508. DOI: 10.1021\/jo00128a024 Murata, M.; Watanabe, S.; Masuda, Y. J. Org. Chem. 1997,\u00a062, 6458. DOI: 10.1021\/jo970963p Murata, M.; Oyama, T.; Watanabe, S.; Masuda, Y. J. Org. Chem.\u00a02000, 65, 164. DOI: 10.1021\/jo991337q Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem.\u00a0Soc. 2002, 124, 8001. DOI: 10.1021\/ja0202255 &lt;review&gt; Ishiyama, T.; Miyaura, N. Chem. Rec. 2004,\u00a03, 271. DOI:\u00a010.1002\/tcr.10068 Shimizu, M.; Hiyama, T. Eur. J. Org. Chem. 2013,\u00a036, [&hellip;]","protected":false},"author":5,"featured_media":18371,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","enabled":false},"version":2}},"categories":[3,2],"tags":[2232,39,2233],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"https:\/\/assets.www.gsbet888.com\/uploads\/2018\/03\/miyaura_boryl_1-e1436605750315.png","jetpack_shortlink":"https:\/\/wp.me\/p96op1-4Mi","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/18370"}],"collection":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/users\/5"}],"replies":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/comments?post=18370"}],"version-history":[{"count":6,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/18370\/revisions"}],"predecessor-version":[{"id":27137,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/18370\/revisions\/27137"}],"wp:featuredmedia":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media\/18371"}],"wp:attachment":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media?parent=18370"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/categories?post=18370"},{"taxonomy":"post_tag","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/tags?post=18370"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}