Synthesis of Chiral Triarylmethanes Bearing All‐Carbon Quaternary Stereocenters: Catalytic Asymmetric Oxidative Cross‐Coupling of 2,2‐Diarylacetonitriles and (Hetero)arenes

Wang Zehua; Zhu Yasheng; Pan Xiaoguang; Wang Gang; Liu Lei

摘要

Abstract >A direct and enantioselective oxidative cross‐coupling of racemic 2,2‐diarylacetonitriles with electron‐rich (hetero)arenes has been described, which allows for efficient construction of triarylmethanes bearing all‐carbon quaternary stereocenters with excellent chemo‐ and enantioselectivity. The reaction has an excellent functional group tolerance, and exhibits a broad scope with respect to both 2,2‐diarylacetonitrile and (hetero)arene components. The rich chemistry of the cyano group allows for facile synthesis of other valuable chiral triarylmethanes bearing all‐carbon quaternary centers that are otherwise difficult to access. </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> 已经描述了具有电子富含电子（异质）植物的外消旋2,2-二芳基乙腈的直接和对映选择性的氧化交联，这允许高效地构建含有全碳季封闭物的三芳基甲烷，具有优异的化学和对映选择性。反应具有优异的官能团耐受性，并且具有相对于2,2-二芳基乙腈和（杂）芳烃组分的宽范围。富含氰基的富含化学物质允许携带所有碳四元中心的其他有价值的手性三芳基甲烷的化合物，否则难以访问。</ 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8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"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Zehua&option=202" target="_blank" rel="nofollow">Wang Zehua;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhu Yasheng&option=202" target="_blank" rel="nofollow">Zhu Yasheng;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Pan Xiaoguang&option=202" target="_blank" rel="nofollow">Pan Xiaoguang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Gang&option=202" target="_blank" rel="nofollow">Wang Gang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liu Lei&option=202" target="_blank" rel="nofollow">Liu Lei;</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>School of Chemistry and Chemical EngineeringShandong UniversityJinan 250100 P. R. China;</p> <p>School of Pharmaceutical SciencesShandong UniversityJinan 250012 P. R. China;</p> <p>School of Pharmaceutical SciencesShandong UniversityJinan 250012 P. R. China;</p> <p>School of Chemistry and Chemical EngineeringShandong UniversityJinan 250100 P. R. China;</p> <p>School of Chemistry and Chemical EngineeringShandong UniversityJinan 250100 P. R. China;</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/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=asymmetric catalysis&option=203" rel="nofollow">asymmetric catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitrile&option=203" rel="nofollow">nitrile;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=oxidative C?H functionalization&option=203" rel="nofollow">oxidative 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=quaternary stereocenter&option=203" rel="nofollow">quaternary stereocenter;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=triarylmethane&option=203" rel="nofollow">triarylmethane;</a> </p> <div class="translation"> 机译：不对称催化;腈;氧化C？H官能化;四核;三芳基甲烷; </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/0704028161177.html">Synthesis of Chiral Triarylmethanes Bearing All‐Carbon Quaternary 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class="tuijian_authcolor"> . 第十届金属有机化学讨论会 </a> <span> <span> . 1998</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020311642706.html">超临界二氧化碳中钯催化芳基碘、内炔和芳基硼酸三组分立体选择性的合成四取代烯烃</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=许秋香&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 许秋香</a> <span> . 2009</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120101066672.html">一种含有取代二苯基和3-吲哚基骨架的手性(R)-三芳基甲烷衍生物及其合成方法</a> <b>[P]</b> . <span> 中国专利： CN110156658A </span> <span> . 2019-08-23</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/061204468975.html">一种钌催化芳基胺化合物的不对称氢化合成手性三级胺的方法</a> <b>[P]</b> . <span> 中国专利： CN109574867B </span> <span> . 2021.06.15</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130438013865.html">Catalytic asymmetric hetero diels-alder reaction of a heteroaromatic C-nitroso dienophile: a novel method for synthesis of chiral non-racemic amino alcohols</a> <b>[P]</b> . <span> 外国专利：  US2005261497A1 </span> <span> . 2005-11-24</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：杂芳族C-亚硝基亲二烯体的催化不对称杂狄尔斯-阿尔德反应：一种合成手性非外消旋氨基醇的新方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130419373975.html">A preparation method of all-carbon quaternary stereocenter compound using 2,2-disubstituted 1,3-propanediol</a> <b>[P]</b> . <span> 外国专利：  KR101233809B1 </span> <span> . 2013-02-18</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：2,2-二取代的1,3-丙二醇的全碳四元立体中心化合物的制备方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130439573291.html">CATALTYTIC ASYMMETRIC HETERO DIELS-ALDER REACTION OF A HETEROAROMATIC C-NITROSO DIENOPHILE: A NOVEL METHOD FOR SYNTHESIS OF CHIRAL NON-RACEMIC AMINO ALCOHOLS</a> <b>[P]</b> . <span> 外国专利：  WO2005068457A1 </span> <span> . 2005-07-28</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：杂多酸C-亚硝基二苯甲醚的不对称异丁二烯的烷基化反应：一种新颖的手性非芳族氨基醇合成方法 </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" 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