Synthesis of (        <i >EE        )‐2‐Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl‐fused 2‐Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst

摘要

Abstract > To date, the synthesis of ( E )‐2‐alkenylazaarenes via the condensation of 2‐methyl N ‐heteroarenes with aldehydes or their equivalents has been well demonstrated. However, the direct formation of such a class of useful compounds from extensively distributed 2‐alkylcyclic amine motifs remains an unresolved goal. Herein, by employing the nitrogen‐silica‐doped carbon (Vulcan XC‐72R) as the support, we have developed a low‐loading cobalt nanocatalyst (Co/ N ‐Si‐C). The combination of such a catalyst with p ‐nitrobenzoic acid and molecular O <sub>2</sub> exhibits excellent catalytic performance towards the dehydrogenative coupling of (hetero)aryl‐fused 2‐alkylcyclic amines with aldehydes to afford the ( E )‐2‐alkenylazaarenes. In the reaction, effective capture of the partially dehydrogenated cyclic amine motifs appears to be the key strategy to address the issue of the chemoselectivity. The developed catalytic transformation proceeds with the merits of broad substrate scope, good functional group tolerance, high atom‐efficiency, use of an earth‐abundant and reusable cobalt catalyst and molecular O <sub>2</sub> as a green oxidant, which offers an important basis for the direct conversion of inert cyclic amine units into the functional frameworks. </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> > 迄今为止，合成（ e </ i> ）-2-链烯基通过2-甲基的缩合 n </ i> - 用醛或它们的等同物进行了很好的证明。然而，从广泛分布的2-烷基环胺基序的直接形成这样一类有用的化合物仍然是未解决的目标。在此，通过使用氮二氧化硅掺杂的碳（Vulcan XC-72R）作为载体，我们开发了一种低负载钴纳米催化剂（CO / n </ i> -si-c）。这种催化剂的组合 p </ i> - 硝基苯甲酸和分子o <sub> 2 </ sub> 表现出优异的催化性能，朝向（杂）芳基熔融2-烷基环胺与醛提供的脱氢偶联，得到（ e </ i> ）-2-链烯基氧基。在反应中，有效捕获部分脱氢的环状胺基序似乎是解决化学选择性问题的关键策略。开发的催化转化具有宽基质范围，良好官能团耐受性，高原子效率，使用土坯和可重复使用的钴催化剂和分子o的优点 <sub> 2 </ sub> 作为一种绿色氧化剂，它为将惰性环胺单元直接转化为功能框架的重要依据。 </ 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-16041/'>《ChemCatChem 》</a> <b style="margin: 0 2px;">|</b><span>2018年第13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"> </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/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=alkenylazaarenes&option=203" rel="nofollow">alkenylazaarenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=aldehydes&option=203" rel="nofollow">aldehydes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cobalt&option=203" rel="nofollow">cobalt;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=dehydrogenative coupling&option=203" rel="nofollow">dehydrogenative coupling;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nanocatalysts&option=203" rel="nofollow">nanocatalysts;</a> </p> <div class="translation"> 机译：链烯氧基;醛;钴;脱氢偶联;纳米催化剂; 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href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张欣&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张欣</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王瑾玲&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,王瑾玲</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=郁铭&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,郁铭</a> <span> <a href="/conference-cn-31983/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化学会全国第五届无机化学学术会议 </a> <span> <span> . 2000</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/02031584493.html">含(1R,2R)-N-[2-(3-茚基)乙基]-N',N'-二甲基-1,2-环己二胺配体稀土配合物的合成及其对分子内氢胺化反应的催化性能研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=唐慕君&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 唐慕君</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120103575355.html">2-(2,2-二芳基乙烯基)-季铵盐型环胺衍生物及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN110981787A </span> <span> . 2020-04-10</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120101106177.html">2-（2，2-二芳基乙烯基）环胺衍生物及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN110240559A </span> <span> . 2019-09-17</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130434145526.html">Preparation of (hetero)aryl, ethers or thioether compound, comprises cross-coupling of primary or secondary amines, alcohols or thioalcohol compound with substituted (hetero)aryl compound in the presence of Bronsted-base and catalyst</a> <b>[P]</b> . <span> 外国专利：  DE102005030400A1 </span> <span> . 2006-12-28</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）芳基，醚或硫醚化合物的制备包括在布朗斯台德碱和催化剂存在下，伯或仲胺，醇或硫醇化合物与取代的（杂）芳基化合物的交叉偶联。 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130414101533.html">MANUFACTURING METHOD OF EGG-SHELL TYPE COBALT/SILICA NANOCATALYSTS FOR FISCHER-TROPSCH SYNTHESIS REACTION AND COBALT/SILICA NANOCATALYSTS THEREOF, MANUFACTURING METHOD OF LIQUID HYDROCARBON USING THE SAME</a> <b>[P]</b> . <span> 外国专利：  KR101524574B1 </span> <span> . 2015-06-04</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：费-托合成反应的蛋壳型钴/二氧化硅纳米催化剂的制备方法及其钴，硅纳米催化剂的制备方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130448191653.html">New alkoxy- and hydroxy-substituted N,N,N-tri((het)aryl-(hetero)alk(e n)yl, (het)aryl-(hetero)alkynyl and (het)aryl-(hetero)cycloalk(en)yl) -amines and salts are used for stabilizing hydroxylamine solution</a> <b>[P]</b> . <span> 外国专利：  DE10008080A1 </span> <span> . 2001-08-23</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：新的烷氧基和羟基取代的N，N，N-三（（杂）芳基-（杂）烷（烯）基），（杂）芳基-（杂）炔基和（杂）芳基-（杂）环烷（烯））yl）-胺和盐用于稳定羟胺溶液 </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('0704022058539','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 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Synthesis of ( EE )‐2‐Alkenylazaarenes via Dehydrogenative Coupling of (Hetero)aryl‐fused 2‐Alkylcyclic Amines and Aldehydes with a Cobalt Nanocatalyst

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