Methyl‐Selective α‐Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN‐AZADO or 1‐Me‐AZADO)

摘要

Abstract > Methyl‐selective α‐oxygenation of tertiary amines is a highly attractive approach for synthesizing formamides while preserving the amine substrate skeletons. Therefore, the development of efficient catalysts that can advance regioselective α‐oxygenation at the N ‐methyl positions using molecular oxygen (O <sub>2</sub> ) as the terminal oxidant is an important subject. In this study, we successfully developed a highly regioselective and efficient aerobic methyl‐selective α‐oxygenation of tertiary amines by employing a Cu/nitroxyl radical catalyst system. The use of moderately hindered nitroxyl radicals, such as 1,5‐dimethyl‐9‐azanoradamantane N ‐oxyl (DMN‐AZADO) and 1‐methyl‐2‐azaadamanane N ‐oxyl (1‐Me‐AZADO), was very important to promote the oxygenation effectively mainly because these N ‐oxyls have longer life‐times than less hindered N ‐oxyls. Various types of tertiary N ‐methylamines were selectively converted to the corresponding formamides. A plausible reaction mechanism is also discussed on the basis of experimental evidence, together with DFT calculations. The high regioselectivity of this catalyst system stems from steric restriction of the amine‐ N ‐oxyl interactions. </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> > 叔胺的甲基选择性α-氧合是一种高度吸引力的方法，用于在保持胺衬底骨架的同时合成甲酰胺。因此，高效催化剂的发展可以推进α-氧合的α-氧合 n </ i> - 使用分子氧的甲基位置（O. <sub> 2 </ sub> 由于末端氧化剂是重要的主题。在这项研究中，我们通过采用Cu / Nitxyl基自由基催化剂体系成功地开发了高度区域选择性和有效的叔胺的有氧甲基选择性α-氧合。使用适度阻碍的硝红素基，如1,5-二甲基-9-氮杂氨烷烷烷 n </ i> - - 氧基（DMN-氮杂）和1-甲基-2-氮杂氨烷 n </ i> - oxylyl（1-me-azado）非常重要，以有效地促进氧合，主要是因为这些 n </ i> - 氧基寿命越长而不是较小的阻碍 n </ i> - 氧基。各种类型的三级 n </ i> - 将甲胺选择性地转化为相应的甲酰胺。还根据实验证据讨论了一种合理的反应机制，以及DFT计算。该催化剂系统的高区域选择性源于胺的空间限制 - n </ i> - 氧基相互作用。 </ 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>2019年第46期</span><b style="margin: 0 2px;">|</b><span>共9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=copper&option=203" rel="nofollow">copper;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=formamides&option=203" rel="nofollow">formamides;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=methyl-selective α-oxygenation&option=203" rel="nofollow">methyl-selective α-oxygenation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=nitroxyl radical&option=203" rel="nofollow">nitroxyl radical;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=tertiary amines&option=203" rel="nofollow">tertiary amines;</a> </p> <div class="translation"> 机译：铜;甲酰胺;甲基选择性α-氧合;硝基氧基;叔胺; </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/0704028165800.html">Methyl‐Selective α‐Oxygenation of Tertiary Amines to Formamides by Employing Copper/Moderately Hindered Nitroxyl Radical (DMN‐AZADO or 1‐Me‐AZADO)</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> </a> <a href="/journal-foreign-19011/" target="_blank" rel="nofollow" class="tuijian_authcolor">Angewandte Chemie .</a> <span>2019</span><span>,第46期</span> </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：通过采用铜/中等阻碍硝基根基（DMN-AZADO或1-ME-AZADO）甲基 - 选择性α-氧化至甲酰酰胺</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/0704011637123.html">One-Electron Oxidation of Sterically Hindered Amines to Nitroxyl Radicals: Intermediate Amine Radical Cations, Aminyl, α-Aminoalkyl, and Aminylperoxyl Radicals</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=O. 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class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：哌啶型空间位阻胺的硝酰基自由基的制备方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130456815454.html">A process for the preparation of the nitroxyl radicals of hindered amines.</a> <b>[P]</b> . <span> 外国专利：  DE69114106T2 </span> <span> . 1996-03-21</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：一种制备受阻胺的硝酰基自由基的方法。 </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 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 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