Chemoselective N‐Alkylation of Indoles in Aqueous Microdroplets

Gnanamani Elumalai; Yan Xin; Zare Richard N.

摘要

Abstract >Many reactions show much faster kinetics in microdroplets than in the bulk phase. Most reported reactions in microdroplets mirror the products found in bulk reactions. However, the unique environment of microdroplets allows different chemistry to occur. In this work, we present the first chemoselective N‐alkylation of indoles in aqueous microdroplets via a three‐component Mannich‐type reaction without using any catalyst. In sharp contrast, bulk reactions using the same reagents with a catalyst yield exclusively C‐alkylation products. The N‐alkylation yield is moderate in microdroplets, up to 53?%. We extended the scope of the microdroplet reaction and obtained a series of new functionalized indole aminals, which are likely to have biological activities. This work clearly indicates that microdroplet reactions can show reactivity quite different from that of bulk‐phase reactions, which holds great potential for developing novel reactivities in microdroplets. </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> >许多反应在微型阶段中显示出微量电池的动力学得多。 Microdroplets中大多数报告的反应镜像散装反应中发现的产品。然而，微型电镀的独特环境允许发生不同的化学。在这项工作中，我们在不使用任何催化剂的情况下通过三组分曼尼希型反应介绍了吲哚吲哚的第一种化学选择性N-烷基化。在鲜明的对比度下，使用相同试剂的批量反应专门具有C-烷基化产物的催化剂产量。 N-烷基化产率在微量滴水中适度，高达53Ω％。我们延长了微量反应反应的范围，并获得了一系列新的官能化吲哚芳基，其可能具有生物活性。这项工作清楚地表明，微型反应反应可以显示与体相反应的反应性，这具有在微量滴电池中开发新的反应性的巨大潜力。</ 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4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=Gnanamani Elumalai&option=202" target="_blank" rel="nofollow">Gnanamani Elumalai;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yan Xin&option=202" target="_blank" rel="nofollow">Yan Xin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zare Richard N.&option=202" target="_blank" rel="nofollow">Zare Richard N.;</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 ChemistryStanford University333 Campus Drive Stanford CA 94305-5080 USA;</p> <p>Department of ChemistryStanford University333 Campus Drive Stanford CA 94305-5080 USA;</p> <p>Department of ChemistryStanford University333 Campus Drive Stanford CA 94305-5080 USA;</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=chemoselectivity&option=203" rel="nofollow">chemoselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=indoles&option=203" rel="nofollow">indoles;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=liquid microdroplets&option=203" rel="nofollow">liquid microdroplets;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=N-alkylation&option=203" rel="nofollow">N-alkylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=reaction acceleration&option=203" rel="nofollow">reaction acceleration;</a> </p> <div class="translation"> 机译：化学选择;吲哚;液体微型电流;N-烷基化;反应加速度; </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"> 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