{"id":1161,"date":"2014-04-24T16:22:26","date_gmt":"2014-04-24T08:22:26","guid":{"rendered":"\/\/www.gsbet888.com\/?p=1161"},"modified":"2019-08-02T18:56:58","modified_gmt":"2019-08-02T10:56:58","slug":"post-1161","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/%e5%81%b6%e8%81%94%e5%8f%8d%e5%ba%94\/2014\/04\/post-1161.html","title":{"rendered":"\u6867\u5c71\u5076\u8054\u53cd\u5e94\uff08Hiyama Cross Coupling\uff09"},"content":{"rendered":"<ul>\n<li><strong>\u6982\u8981<\/strong><\/li>\n<\/ul>\n<p>\u5364\u4ee3\u82b3\u70c3\u30fb\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e0e\u6709\u673a\u7845\u70f7\u5728\u94af\u50ac\u5316\u5242\u5b58\u5728\u4e0b\u7684\u5076\u8054\u53cd\u5e94\u3002<\/p>\n<p>\u6709\u673a\u7845\u70f7\u901a\u5e38\u6761\u4ef6\u4e0b\u662f\u6781\u5176\u7a33\u5b9a\u7684\uff0c\u4e3a\u4e86\u80fd\u4f7f\u5176\u5e94\u7528\u4e8e\u5076\u8054\u53cd\u5e94\u4e2d\uff0c\u901a\u5e38\u9700\u8981\u6dfb\u52a0\u542bF\u7684Lewis\u78b1\u6d3b\u5316\u5242\uff0c\u5728\u91d1\u5c5e\u8f6c\u79fb\u7684\u65f6\u5019\u5f62\u6210\u6d3b\u5316\u7684\u9ad8\u914d\u4f4d\u7684\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\u3002<\/p>\n<p>\u7845\u4e0a\u7684\u53d6\u4ee3\u57fa\u901a\u5e38\u5fc5\u987b\u662f\u6742\u539f\u5b50\u6216\u8005\u82ef\u57fa\u3002\u5982\u679c\u662f\u4e09\u70f7\u57fa\u7532\u7845\u70f7\uff0c\u5219\u96be\u4ee5\u5f62\u6210\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\uff0c\u6240\u4ee5\u5076\u8054\u53cd\u5e94\u8f83\u96be\u8fdb\u884c\u3002<\/p>\n<p>\u7845\u5177\u6709\u4f4e\u6bd2\u6027\u30fb\u4f4e\u73af\u5883\u8d1f\u8377\u6027\u7b49\u4f18\u70b9\uff0c\u662f\u4e00\u4e2a\u5f88\u6709\u6f5c\u529b\u7684\u53cd\u5e94\u3002\u4f46\u662f\u76ee\u524d\u6765\u8bf4\uff0c\u6742\u539f\u5b50\u53d6\u4ee3\u7684\u7845\u70f7\u5316\u5408\u7269\u5728\u4e00\u822c\u7684\u5408\u6210\u53cd\u5e94\u4e2d\u4f7f\u7528\u9891\u7387\u6bd4\u8f83\u4f4e\uff0c\u76f8\u6bd4\u4e8e<a style=\"color: #669900\" href=\"http:\/\/www.chem-station.com\/user-cgi-bin\/odoos\/ps_search.cgi?act=jump&amp;access=1&amp;url=http%3a%2f%2fwww%2echem%2dstation%2ecom%2fodoos%2fdata%2fx%2dene%2d3%2ehtm\">\u9234\u6728-\u5bae\u6d66<\/a>\u5076\u8054\u53cd\u5e94\u6765\u8bf4\uff0c\u5e94\u7528\u8fd8\u4e0d\u5e7f\u6cdb\u3002<\/p>\n<p>\u7094\u70c3\u7684\u7845\u6c22\u52a0\u6210\u53ef\u4ee5\u5408\u6210\u4e59\u70ef\u57fa\u7845\u70f7\u3002\u56e0\u6b64\u53ef\u4ee5\u7528\u6765\u5408\u6210\u787c\u6c22\u5316\u53cd\u5e94\u5b9e\u73b0\u4e0d\u4e86\u7684\u4f4d\u7f6e\u9009\u62e9\u6027\u53cd\u5e94\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n<p>\u30fbHatanaka, Y.; Hiyama, T.\u00a0<em>J. Org. Chem.<\/em>\u00a0<strong style=\"color: #ff6600\">1988<\/strong>,\u00a0<em>53<\/em>, 918. doi:<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/jo00239a056\">10.1021\/jo00239a056<\/a><br \/>\n\u30fbHiyama, T.; Hatanaka, Y.<em>\u00a0Pure. Appl. Chem.\u00a0<\/em><strong style=\"color: #ff6600\">1994<\/strong>.\u00a0<em>66<\/em>, 1471.<br \/>\n\u30fbHiyama, T.\u00a0<em>J. Organomet. Chem.<\/em>\u00a0<strong style=\"color: #ff6600\">2002<\/strong>,\u00a0<em>653<\/em>, 58.<br \/>\n\u30fbDenmark, S. E.; Obar, M. H.\u00a0<em>Aldrichimica Acta<\/em>\u00a0<strong style=\"color: #ff6600\">2003<\/strong>,\u00a0<em>36<\/em>, 75.\u00a0<a style=\"color: #669900\" href=\"http:\/\/www.sigmaaldrich.com\/etc\/medialib\/docs\/Aldrich\/Acta\/al_acta_38_3.pdf\">[PDF]<\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n<p>\u6709\u673a\u7845\u70f7\u6bd4\u8f83\u7a33\u5b9a\uff0c\u5728\u542bF\u7684\u8def\u6613\u65af\u78b1\u7684\u4f5c\u7528\u4e0b\u8fdb\u884c\u91d1\u5c5e\u8f6c\u79fb\u5f62\u6210\u6d3b\u6027\u7684\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\u8fdb\u884c\u6574\u4e2a\u53cd\u5e94\u5faa\u73af\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_2.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1168\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_2.gif\" alt=\"hiyama_coupling_2\" width=\"372\" height=\"171\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n<p>\u73af\u4e01\u7845\u70f7\u7531\u4e8e\u5176\u626d\u66f2\u7684\u7ed3\u6784\uff0c\u5bfc\u81f4\u5176\u62e5\u6709\u6bd4\u8def\u6613\u65af\u9178\u66f4\u9ad8\u7684\u9178\u6027\u3002\u6240\u4ee5\u5728\u6e29\u548c\u7684\u6761\u4ef6\u4e0b\uff0c\u53ef\u4ee5\u5e94\u7528\u4e8eHiyama\u5076\u8054\u53cd\u5e94\u3002[1]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_4.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1171\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_4.gif\" alt=\"hiyama_coupling_4\" width=\"373\" height=\"62\" \/><\/a><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_5.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1172\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_5.gif\" alt=\"hiyama_coupling_5\" width=\"233\" height=\"94\" \/><\/a><\/p>\n<p>\u5229\u7528\u5177\u6709\u914d\u4f4d\u6027\u7684\u5421\u5576\u7845\u70f7\u8fdb\u884c\u5076\u8054\u53cd\u5e94\uff0c\u53ef\u4ee5\u5b8c\u7f8e\u7684\u5408\u6210\u6bd4\u8f83\u56f0\u96be\u7684\u4f4d\u7f6e\u9009\u62e9\u6027\u7684\u56db\u53d6\u4ee3\u70ef\u70c3\u3002[2]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_6.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1173\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_6.gif\" alt=\"hiyama_coupling_6\" width=\"439\" height=\"151\" \/><\/a><\/p>\n<p>\u5229\u7528\u5982\u56fe\u8bbe\u8ba1\u7684\u82ef\u57fa\u7845\u70f7\u7684\u884d\u751f\u7269\u4f5c\u4e3a\u5e95\u7269\uff0c\u4e0d\u9002\u7528\u542bF\u8def\u6613\u65af\u78b1\u4e5f\u80fd\u6709\u6548\u8fdb\u884cHiyama\u5076\u8054\u53cd\u5e94\u3002\u540c\u65f6\u751f\u6210\u7684\u7845\u70f7\u5316\u5408\u7269\u53ef\u4ee5\u88ab\u91cd\u590d\u5229\u7528\u3002[3]\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_3.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1174\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_3.gif\" alt=\"hiyama_coupling_3\" width=\"378\" height=\"80\" \/><\/a><\/p>\n<p>\u6709\u673a\u7845\u70f7\u9187\u53ef\u4ee5\u5229\u7528\u5ec9\u4ef7\u7684TMSOK\u6d3b\u5316\u540e\u4e5f\u80fd\u8fdb\u884cHiyama\u5076\u8054\u53cd\u5e94\u3002[4]\u8fd9\u6837\u7684\u8bdd\u5bf9\u4e8e\u62e5\u6709\u5728\u542bF\u8bd5\u5242\u5b58\u5728\u4e0b\u4e0d\u7a33\u5b9a\u5b98\u80fd\u56e2\u7684\u5e95\u7269\u540c\u6837\u4e5f\u80fd\u8fdb\u884c\u5076\u8054\u53cd\u5e94\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_7.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-1175\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/04\/hiyama_coupling_7.gif\" alt=\"hiyama_coupling_7\" width=\"337\" height=\"108\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6280\u5de7<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n[1] Denmark, S. E.; Choi, J. Y.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">1999<\/strong>,\u00a0<em>121<\/em>, 5821. DOI:\u00a0<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja9908117\">10.1021\/ja9908117<\/a><br \/>\n[2] Itami, K.; Kamei, T.; Yoshida,J.-i.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">2003<\/strong>,\u00a0<em>125<\/em>, 14670. DOI:\u00a0<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja037566i\">10.1021\/ja037566i\u00a0<\/a><br \/>\n[3] Nakao, Y.; Imanaka, H.; Sahoo, A. H.; Yada, A.; Hiyama, T.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">2005<\/strong>,\u00a0<em>127<\/em>, 6952. DOI:<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja051281j\">10.1021\/ja051281j<\/a><br \/>\n[4] (a) Denmark, S. E.; Sweis, R. F.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">2001<\/strong>,\u00a0<em>123<\/em>, 6439. DOI:\u00a0<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja016021q\">10.1021\/ja016021q<\/a>\u00a0For mechanistic implications, see: (b) Denmark, S. E. et al.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">2004<\/strong>,\u00a0<em>126<\/em>, 4865. DOI:<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja037234d\">10.1021\/ja037234d<\/a>\u00a0(c) Denmark, S. E.; Sweis, R. F.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong style=\"color: #ff6600\">2004<\/strong>,\u00a0<em>126<\/em>, 4876. DOI:<a style=\"color: #669900\" href=\"http:\/\/dx.doi.org\/10.1021\/ja0372356\">10.1021\/ja0372356\u00a0<\/a><\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp; <\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u5364\u4ee3\u82b3\u70c3\u30fb\u82b3\u57fa\u4e09\u6c1f\u7532\u78fa\u9178\u916f\u4e0e\u6709\u673a\u7845\u70f7\u5728\u94af\u50ac\u5316\u5242\u5b58\u5728\u4e0b\u7684\u5076\u8054\u53cd\u5e94\u3002 \u6709\u673a\u7845\u70f7\u901a\u5e38\u6761\u4ef6\u4e0b\u662f\u6781\u5176\u7a33\u5b9a\u7684\uff0c\u4e3a\u4e86\u80fd\u4f7f\u5176\u5e94\u7528\u4e8e\u5076\u8054\u53cd\u5e94\u4e2d\uff0c\u901a\u5e38\u9700\u8981\u6dfb\u52a0\u542bF\u7684Lewis\u78b1\u6d3b\u5316\u5242\uff0c\u5728\u91d1\u5c5e\u8f6c\u79fb\u7684\u65f6\u5019\u5f62\u6210\u6d3b\u5316\u7684\u9ad8\u914d\u4f4d\u7684\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\u3002 \u7845\u4e0a\u7684\u53d6\u4ee3\u57fa\u901a\u5e38\u5fc5\u987b\u662f\u6742\u539f\u5b50\u6216\u8005\u82ef\u57fa\u3002\u5982\u679c\u662f\u4e09\u70f7\u57fa\u7532\u7845\u70f7\uff0c\u5219\u96be\u4ee5\u5f62\u6210\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\uff0c\u6240\u4ee5\u5076\u8054\u53cd\u5e94\u8f83\u96be\u8fdb\u884c\u3002 \u7845\u5177\u6709\u4f4e\u6bd2\u6027\u30fb\u4f4e\u73af\u5883\u8d1f\u8377\u6027\u7b49\u4f18\u70b9\uff0c\u662f\u4e00\u4e2a\u5f88\u6709\u6f5c\u529b\u7684\u53cd\u5e94\u3002\u4f46\u662f\u76ee\u524d\u6765\u8bf4\uff0c\u6742\u539f\u5b50\u53d6\u4ee3\u7684\u7845\u70f7\u5316\u5408\u7269\u5728\u4e00\u822c\u7684\u5408\u6210\u53cd\u5e94\u4e2d\u4f7f\u7528\u9891\u7387\u6bd4\u8f83\u4f4e\uff0c\u76f8\u6bd4\u4e8e\u9234\u6728-\u5bae\u6d66\u5076\u8054\u53cd\u5e94\u6765\u8bf4\uff0c\u5e94\u7528\u8fd8\u4e0d\u5e7f\u6cdb\u3002 \u7094\u70c3\u7684\u7845\u6c22\u52a0\u6210\u53ef\u4ee5\u5408\u6210\u4e59\u70ef\u57fa\u7845\u70f7\u3002\u56e0\u6b64\u53ef\u4ee5\u7528\u6765\u5408\u6210\u787c\u6c22\u5316\u53cd\u5e94\u5b9e\u73b0\u4e0d\u4e86\u7684\u4f4d\u7f6e\u9009\u62e9\u6027\u53cd\u5e94\u3002 &nbsp; \u57fa\u672c\u6587\u732e \u30fbHatanaka, Y.; Hiyama, T.\u00a0J. Org. Chem.\u00a01988,\u00a053, 918. doi:10.1021\/jo00239a056 \u30fbHiyama, T.; Hatanaka, Y.\u00a0Pure. Appl. Chem.\u00a01994.\u00a066, 1471. \u30fbHiyama, T.\u00a0J. Organomet. Chem.\u00a02002,\u00a0653, 58. \u30fbDenmark, S. E.; Obar, M. H.\u00a0Aldrichimica Acta\u00a02003,\u00a036, 75.\u00a0[PDF] &nbsp; \u53cd\u5e94\u673a\u7406 \u6709\u673a\u7845\u70f7\u6bd4\u8f83\u7a33\u5b9a\uff0c\u5728\u542bF\u7684\u8def\u6613\u65af\u78b1\u7684\u4f5c\u7528\u4e0b\u8fdb\u884c\u91d1\u5c5e\u8f6c\u79fb\u5f62\u6210\u6d3b\u6027\u7684\u7845\u9178\u76d0\u4e2d\u95f4\u4f53\u8fdb\u884c\u6574\u4e2a\u53cd\u5e94\u5faa\u73af\u3002 &nbsp; \u53cd\u5e94\u5b9e\u4f8b \u73af\u4e01\u7845\u70f7\u7531\u4e8e\u5176\u626d\u66f2\u7684\u7ed3\u6784\uff0c\u5bfc\u81f4\u5176\u62e5\u6709\u6bd4\u8def\u6613\u65af\u9178\u66f4\u9ad8\u7684\u9178\u6027\u3002\u6240\u4ee5\u5728\u6e29\u548c\u7684\u6761\u4ef6\u4e0b\uff0c\u53ef\u4ee5\u5e94\u7528\u4e8eHiyama\u5076\u8054\u53cd\u5e94\u3002[1] \u5229\u7528\u5177\u6709\u914d\u4f4d\u6027\u7684\u5421\u5576\u7845\u70f7\u8fdb\u884c\u5076\u8054\u53cd\u5e94\uff0c\u53ef\u4ee5\u5b8c\u7f8e\u7684\u5408\u6210\u6bd4\u8f83\u56f0\u96be\u7684\u4f4d\u7f6e\u9009\u62e9\u6027\u7684\u56db\u53d6\u4ee3\u70ef\u70c3\u3002[2] \u5229\u7528\u5982\u56fe\u8bbe\u8ba1\u7684\u82ef\u57fa\u7845\u70f7\u7684\u884d\u751f\u7269\u4f5c\u4e3a\u5e95\u7269\uff0c\u4e0d\u9002\u7528\u542bF\u8def\u6613\u65af\u78b1\u4e5f\u80fd\u6709\u6548\u8fdb\u884cHiyama\u5076\u8054\u53cd\u5e94\u3002\u540c\u65f6\u751f\u6210\u7684\u7845\u70f7\u5316\u5408\u7269\u53ef\u4ee5\u88ab\u91cd\u590d\u5229\u7528\u3002[3] \u6709\u673a\u7845\u70f7\u9187\u53ef\u4ee5\u5229\u7528\u5ec9\u4ef7\u7684TMSOK\u6d3b\u5316\u540e\u4e5f\u80fd\u8fdb\u884cHiyama\u5076\u8054\u53cd\u5e94\u3002[4]\u8fd9\u6837\u7684\u8bdd\u5bf9\u4e8e\u62e5\u6709\u5728\u542bF\u8bd5\u5242\u5b58\u5728\u4e0b\u4e0d\u7a33\u5b9a\u5b98\u80fd\u56e2\u7684\u5e95\u7269\u540c\u6837\u4e5f\u80fd\u8fdb\u884c\u5076\u8054\u53cd\u5e94\u3002 &nbsp; \u5b9e\u9a8c\u6b65\u9aa4 &nbsp; \u5b9e\u9a8c\u6280\u5de7 &nbsp; \u53c2\u8003\u6587\u732e [1] Denmark, S. E.; Choi, J. Y.\u00a0J. Am. Chem. Soc.\u00a01999,\u00a0121, 5821. DOI:\u00a010.1021\/ja9908117 [2] Itami, K.; Kamei, T.; Yoshida,J.-i.\u00a0J. Am. Chem. Soc.\u00a02003,\u00a0125, 14670. DOI:\u00a010.1021\/ja037566i\u00a0 [3] Nakao, Y.; Imanaka, H.; Sahoo, A. H.; Yada, A.; Hiyama, T.\u00a0J. Am. Chem. Soc.\u00a02005,\u00a0127, 6952. DOI:10.1021\/ja051281j [4] (a) Denmark, S. E.; Sweis, R. F.\u00a0J. Am. Chem. Soc.\u00a02001,\u00a0123, 6439. DOI:\u00a010.1021\/ja016021q\u00a0For mechanistic implications, see: (b) Denmark, S. 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