Mechanisms and stereoselectivities of phosphine‐catalyzed (3+3) cycloaddition reaction between azomethine imine and ynone: A computational study

Li Yan; Fu Wenwen; Tian Ruixue; Liang Changhai

摘要

Abstract > To understand the mechanisms and origins of stereoselectivities in PPh <sub> 3 </sub> ‐catalyzed (3?+?3) cycloaddition reaction of but‐3‐yn‐2‐one with azomethine imine, density functional theory (DFT) and ReaxFF molecular dynamics (MD) simulations have been conducted. Various possible reaction pathways have been examined. DFT calculations indicate that this reaction is initiated by nucleophilic attack of catalyst PPh <sub> 3 </sub> to but‐3‐yn‐2‐one to form intermediate 1 , followed by proton transfer leads to intermediate 2 . The subsequent nucleophilic addition of 2 to azomethine imine forms intermediate 3 . Then, intermediate 3 undergoes intramolecular cycloaddition, 1,2‐proton transfer, and elimination of catalyst affording the final product. A trace amount of PhOH plays an important role in the proton transfer process. For the stereoselectivity determining C?C bond formation step, both DFT calculations and MD simulations demonstrate that the R‐configured P(R) is the predominant product. Furthermore, high Z/E ‐selectivity is predicted for the studied reaction. Our computational results are in good agreement with previous experimental observations. The present study should be useful to the development of this kind reaction in the future. </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> >了解 PPH </ B> <sub中的立体化功能的机制和起源> 3 </ sup> -catalyzed（3？+α3）环加成反应 - 3-yn-2-oon，具有氮杂甲酰胺亚胺，密度函数理论（DFT）和Reaxff分子动力学（MD已经进行了模拟。已经检查了各种可能的反应途径。 DFT计算表明该反应是通过催化剂的亲核攻击引发催化剂的亲核攻击 3 / b> </ b>〜-3- yN-2-1形成中间体< B> 1 </ b>，然后质子转移导致中间体 2 </ b>。随后的亲核加入 2 - 偶氮甲基亚胺形成中间体 3 / b>。然后，中间体 3>经历分子内环加成，1,2-质子转移，并消除催化剂，得到最终产物。痕量的PHOH在质子转移过程中起重要作用。对于确定C？C键形成步骤的立体选择性，DFT计算和MD仿真都表明R配置的<B> P（R）</ B>是主要产品。此外，预测研究的高 Z / E </ i>用于研究的反应。我们的计算结果与先前的实验观察结果良好。本研究应该对未来发展这种反应的有用。 </ 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-21753/'>《International Journal of Quantum Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第21期</span><b style="margin: 0 2px;">|</b><span>共12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=Li Yan&option=202" target="_blank" rel="nofollow">Li Yan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Fu Wenwen&option=202" target="_blank" rel="nofollow">Fu Wenwen;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tian Ruixue&option=202" target="_blank" rel="nofollow">Tian Ruixue;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Liang Changhai&option=202" target="_blank" rel="nofollow">Liang Changhai;</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 Petroleum and Chemical Engineering Dalian University of TechnologyPanjin China;</p> <p>School of Petroleum and Chemical Engineering Dalian University of TechnologyPanjin China;</p> <p>School of Petroleum and Chemical Engineering Dalian University of TechnologyPanjin China;</p> <p>School of Petroleum and Chemical Engineering Dalian University of TechnologyPanjin 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/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></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=(3+3) cycloaddition&option=203" rel="nofollow">(3+3) cycloaddition;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=density functional theory&option=203" rel="nofollow">density functional theory;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=molecular dynamics simulation&option=203" rel="nofollow">molecular dynamics simulation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=reaction mechanisms&option=203" rel="nofollow">reaction mechanisms;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=stereoselectivity&option=203" rel="nofollow">stereoselectivity;</a> </p> <div class="translation"> 机译：（3 + 3）环加成;密度泛函理论;分子动力学模拟;反应机制;立体选择性; </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/0704019755940.html">Mechanisms and stereoselectivities of phosphine‐catalyzed (3+3) cycloaddition reaction between azomethine imine and ynone: A computational study</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Yan&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Li Yan,</a> <a 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US10758895B2 </span> <span> . 2020-09-01</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：Cu（I）催化的叠氮化物-炔烃环加成（CuAAC）配体和进行Cu（I）催化的叠氮化物-炔烃环加成反应的方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130410182267.html">CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITIONS (CUAAC) LIGANDS AND METHODS FOR CARRYING OUT CU(I)-CATALYZED AZIDE-ALKYNE CYCLOADDITION REACTIONS</a> <b>[P]</b> . <span> 外国专利：  US2017297008A1 </span> <span> . 2017-10-19</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：CU（I）催化的叠氮化物-炔烃环化反应（CUAAC）配体和进行CU（I）催化的叠氮化物-炔烃环化反应的方法 </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 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