Synthesis of gem‐Difluoro Olefins through C?H Functionalization and β‐fluoride Elimination Reactions

摘要

Abstract >A palladium catalyzed C?H functionalization and consecutive β‐fluoride elimination reaction between indole heterocycles and fluorinated diazoalkanes is reported. This approach provides for the first time a facile method for the rapid synthesis of gem‐difluoro olefins using fluorinated diazoalkanes under mild reaction conditions. Cyclopropanation products were obtained when N‐arylated rather than N‐alkylated indoles were applied in this reaction. Mechanistic studies reveal the importance of the β‐fluoride elimination step in this transformation. This method presents a new concept for the simple and direct transfer of a 1‐aryl‐(2,2‐difluorovinyl) group to access gem‐difluoro olefins. </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 Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> 据报道，催化催化剂和氟金杂环和氟化二氮烷烃之间的连续β-氟化物消除反应。该方法提供了在温和的反应条件下使用氟化二氮杂烷烃快速合成宝石 - 二氟烯烃的容易方法。当在该反应中施加N-芳基化而不是N-烷基化的吲哚时，获得环丙烷产物。机械研究揭示了β-氟化物消除步骤在该转化中的重要性。该方法呈现了一种新的概念，用于1-芳基（2,2-二氟乙烯基）基团的简单和直接转移以进入宝石 - 二氟烯烃。</ p> </摘要> </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-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第14期</span><b style="margin: 0 2px;">|</b><span>共5页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> </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"> </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/1188.html" title="应用化学">应用化学;</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=carbene transfer&option=203" rel="nofollow">carbene transfer;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=C?H functionalization&option=203" rel="nofollow">C?H functionalization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fluorine&option=203" rel="nofollow">fluorine;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=gem-difluoro olefins&option=203" rel="nofollow">gem-difluoro olefins;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=palladium&option=203" rel="nofollow">palladium;</a> </p> <div class="translation"> 机译：卡贝转移;C？H官能化;氟;宝石 - 二氟烯烃;钯; </div> </li> </ul> </div> </div> <div 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</span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105297405.html">用于光化学反应的末端官能化全氟(烷基乙烯基醚)的官能化共聚物的反应器壁、增加烃和卤代烃的氟含量的方法和烯烃的制备</a> <b>[P]</b> . <span> 中国专利： CN101090767A </span> <span> . 2007-12-19</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120251564.html">烃一级C－H键的选择性的、催化的和热诱导的官能化反应</a> <b>[P]</b> . <span> 中国专利： CN1253459C </span> <span> . 2006.04.26</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130434127990.html">Synthesis of olefin from synthesis gas comprises introducing a synthesis gas into the beneath of the zone of a reaction column and removing the obtained olefin from the beneath of the inlet for the synthesis gas</a> <b>[P]</b> . <span> 外国专利：  DE102005056784A1 </span> <span> . 2007-05-31</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：由合成气合成烯烃的步骤包括将合成气引入反应塔区域的下部，并从合成气入口的下部除去获得的烯烃。 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130432342719.html">FUNCTIONALIZED COPOLYMERS OF TERMINALLY FUNCTIONALIZED PERFLUORO (ALKYL VINYL ETHER) REACTOR WALL FOR PHOTOCHEMICAL REACTIONS, PROCESS FOR INCREASING FLUORINE CONTENT IN HYDROCARBONS AND HALOHYDROCARBONS AND OLEFIN PRODUCTION</a> <b>[P]</b> . <span> 外国专利：  EP1855795A1 </span> <span> . 2007-11-21</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：末端功能性全氟（烷基乙烯基醚）反应器的功能性共聚物壁，用于光化学反应，增加烃和卤代烃中氟含量的过程以及烯烃的生产 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130433195539.html">Functionalized Copolymers of Terminally Functionalized Perfluoro (Alkyl Vinyl Ether) Reactor Wall for Photochemical Reactions, Process for Increasing Fluorine Content in Hydrocaebons and Halohydrocarbons and Olefin Production</a> <b>[P]</b> . <span> 外国专利：  US2007265368A1 </span> <span> . 2007-11-15</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：用于光化学反应的末端官能化全氟（烷基乙烯基醚）反应器壁的官能化共聚物，用于增加烃类和卤代烃中氟含量的方法以及烯烃的生产 </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: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704028161183','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" 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