Preparation of Building Blocks for Iterative Suzuki‐Miyaura Reactions via Direct Bromination of Aryl Boronic Acids: One‐Pot Total Syntheses of Dictyoterphenyls A and B

Lee Chun‐Young; Cheon Cheol‐Hong

摘要

Abstract >A highly efficient method for the preparation of 4‐alkoxy‐3‐bromophenyl boronic acid N‐methyliminodiacetic acid (MIDA) esters as building blocks in iterative Suzuki‐Miyaura reactions from the 4‐alkoxyphenylboronic acids is described using a boronic acid moiety as a blocking group in bromination reactions. With these MIDA boronates, the total syntheses of dictyoterphenyls A and B were developed in only two separate one‐pot operations. Furthermore, we have developed a more practical protocol for the preparation of meta‐terphenyl natural products by simply adding the second aryl halide and water to the reaction mixture via the controlled release technique. > <blockFixed type="graphic"> <mediaResourceGroup> <mediaResource alt="image" href="urn:x-wiley:16154150:media:adsc201700733:adsc201700733-toc-0001"/> </mediaResourceGroup> </blockFixed> </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><abstract xmlns =“http://www.wiley.com/namespaces/wiley”type =“main”xml：lang =“en”> <title type =“main”>抽象</ title> > a高度使用硼酸部分将使用硼酸部分作为封闭基团描述作为从4-烷氧基苯甲酸的迭代铃木霉菌的结构中制备4-烷氧基-3-溴苯乙烯基硼酸N-甲基氨基二乙酰硼酸（Mida）酯的高效方法溴化反应。利用这些MIDA硼酸盐，只有两个单独的单盆操作，开发了双滴苯基A和B的总合成。此外，我们通过通过控制释放技术简单地将第二芳基卤化物和水加入反应混合物，制定了更实用的方案，用于制备荟萃三苯基天然产物。</ p> > <块状晶片类型=“图形“> <mediaresourcegroup> <mediaresource alt =”图像“href =”urn：X-Wiley：16154150：媒体：ADSC201700733：ADSC201700733-TOC-0001“/> </ METIARESOURCEGROUP> </ BlockFixed> </ P> </ Abstract > </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-19407/'>《Advanced synthesis & catalysis》</a> <b style="margin: 0 2px;">|</b><span>2017年第21期</span><b style="margin: 0 2px;">|</b><span>共6页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Chun‐Young&option=202" target="_blank" rel="nofollow">Lee Chun‐Young;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cheon Cheol‐Hong&option=202" target="_blank" rel="nofollow">Cheon Cheol‐Hong;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Department of ChemistryKorea University145 Anam-ro Seongbuk-gu Seoul 02841 Republic of Korea;</p> <p>Department of ChemistryKorea University145 Anam-ro Seongbuk-gu Seoul 02841 Republic of Korea;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/238.html" title="化学工业">化学工业;</a><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a><a href="https://www.zhangqiaokeyan.com/clc/7777.html" title="化学反应过程">化学反应过程;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Blocking Group&option=203" rel="nofollow">Blocking Group;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dictyoterphenyls A and B&option=203" rel="nofollow">Dictyoterphenyls A and B;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Iterative Suzuki-Miyaura reaction&option=203" rel="nofollow">Iterative Suzuki-Miyaura reaction;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=MIDA Boronates&option=203" rel="nofollow">MIDA Boronates;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pot-economy&option=203" rel="nofollow">Pot-economy;</a> </p> <div class="translation"> 机译：阻断组;Dictyoterphenyls A和B;迭代铃木 - 宫颈反应;Mida硼酸盐;电池经济物; </div> </li> </ul> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704022693929.html">Preparation of Building Blocks for Iterative Suzuki‐Miyaura Reactions via Direct Bromination of Aryl Boronic Acids: One‐Pot Total Syntheses of Dictyoterphenyls A and B</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lee Chun‐Young&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Lee Chun‐Young,</a> <a 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class="tuijian_authcolor"> . 2005年全国药物化学会议 </a> <span> <span> . 2005</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/02031130301.html">非膦钯配合物的合成及其催化直接芳基化反应与Suzuki反应的研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=欧阳嘉盛&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 欧阳嘉盛</a> <span> . 2017</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120101131347.html">三甲基苯基三溴化铵的合成方法及萘普生生产中三甲基苯基三溴化铵的回收方法</a> <b>[P]</b> . <span> 中国专利： CN110256257A </span> <span> . 2019-09-20</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120110430235.html">一种用于乙基三苯基溴化膦制备的反应釜</a> <b>[P]</b> . <span> 中国专利： CN107930565A </span> <span> . 2018-04-20</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130420246463.html">PROCESS FOR THE PREPARATION OF BIARILS BY REACTIONS OF SUZUKI-MIYAURA INTO SUPERCRYTICAL CARBON DIOXIDE, CATALYSED BY PALADIUM (II) COMPLEXES WITH OXADIAZOLINS AND CETOIMINES</a> <b>[P]</b> . <span> 外国专利：  PT105634B </span> <span> . 2013-05-02</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：铃木-宫城由钯（II）配合物与恶二唑和乙二亚胺催化合成超结晶二氧化碳的方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130422841261.html">PROCESS FOR THE PREPARATION OF BIARILS BY REACTIONS OF SUZUKI-MIYAURA INTO SUPERCRYTICAL CARBON DIOXIDE, CATALYSED BY PALADIUM (II) COMPLEXES WITH OXADIAZOLINS AND CETOIMINES</a> <b>[P]</b> . <span> 外国专利：  PT105634A </span> <span> . 2012-10-19</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：铃木-宫城由钯（II）配合物与恶二唑和乙二亚胺催化合成超结晶二氧化碳的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130436446530.html">Preparation of 6-(3-(1-adamantyl)-4-methoxyphenyl)-2-naphthoic acid comprises reacting 3-adamantyl-4-methoxyphenyl-boronic acid with 6-bromo-2-naphthoic acid by Suzuki reaction</a> <b>[P]</b> . <span> 外国专利：  FR2884248A1 </span> <span> . 2006-10-13</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：制备6-（3-（1-金刚烷基）-4-甲氧基苯基）-2-萘甲酸包括通过Suzuki反应将3-金刚烷基-4-甲氧基苯基硼酸与6-溴-2-萘甲酸反应 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 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