N‐Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides

Mavroskoufis Andreas; Rajes Keerthana; Golz Paul; Agrawal Arush; Ru? Vincent; G?tze Jan P.; Hopkinson Matthew N.

摘要

Abstract > The combination of light activation and N‐heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA‐light‐mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD‐DFT calculations support a mechanism involving the photoactivation of an ortho ‐toluoyl azolium intermediate, which exhibits “ketone‐like” photochemical reactivity under UVA irradiation. Using this photo‐NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman‐1‐one derivatives. </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> > 光活化和N-杂环（NHC）有机能分解的组合使得使用酸氟化物作为紫外线介导的光化学转化中的底物仅用芳族醛和酮类。化学计量研究和TD-DFT计算支持涉及涉及拍摄的机制 ortho </ i> -Toluoyl氮杂化合物中间体，其在UVA辐射下表现出“酮样”光化学反应性。使用该光电NHC催化方法，开发了一种新颖的光电图/ DIELS-ALDER（PEDA）工艺，导致不同的等色-1-ONE衍生物。 </ 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=Mavroskoufis Andreas&option=202" target="_blank" rel="nofollow">Mavroskoufis Andreas;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Rajes Keerthana&option=202" target="_blank" rel="nofollow">Rajes Keerthana;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Golz Paul&option=202" target="_blank" rel="nofollow">Golz Paul;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Agrawal Arush&option=202" target="_blank" rel="nofollow">Agrawal Arush;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ru? Vincent&option=202" target="_blank" rel="nofollow">Ru? Vincent;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=G?tze Jan P.&option=202" target="_blank" rel="nofollow">G?tze Jan P.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hopkinson Matthew N.&option=202" target="_blank" rel="nofollow">Hopkinson Matthew 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>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</p> <p>Institute of Chemistry and BiochemistryFreie Universit?t BerlinTakustra?e 3 14195 Berlin Germany;</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=acid fluorides&option=203" rel="nofollow">acid fluorides;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=N-heterocyclic carbenes&option=203" rel="nofollow">N-heterocyclic carbenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=organocatalysis&option=203" rel="nofollow">organocatalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photochemistry&option=203" rel="nofollow">photochemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoenolization&option=203" rel="nofollow">photoenolization;</a> </p> <div class="translation"> 机译：酰氟;正杂环碳;有机成分;光化学;光电化; 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