Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C?H Activation

Uryu Mizuho; Hiraga Taito; Koga Yoshito; Saito Yutaro; Murakami Kei; Itami Kenichiro

摘要

Abstract >Polycyclic aromatic hydrocarbons (PAHs) represent an emerging class of π‐conjugated molecules in the area of optoelectronic devices and materials. Unprecedented synthetic routes to various PAHs from simple phenol derivatives by a palladium‐catalyzed annulative dimerization of phenylene triflate through twofold inter‐ and intramolecular C?H activation have been established. The initially formed partially fused PAHs can be smoothly transformed into a variety of fully fused PAHs by the Scholl reaction. Furthermore, the reactions of phenanthrene‐substituted aryl triflates proceeded regioselectively. The findings inspired the development of a rapid and efficient synthesis of polybenzoacene derivatives. This study not only allows transformation of phenyl triflates, but also discloses a new retrosynthetic strategy towards PAHs, especially polybenzoacenes. </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> >多环芳烃（PAH）代表光电器件和材料面积的π缀合分子的新出现类。通过钯催化的亚苯基衍生物通过双重和分子内C-和分子内C-H-H激活，通过钯催化的环氧衍生物从简单的苯酚衍生物到各种PAHs的前所未有的合成途径。最初形成的部分融合的PAH可以通过Scholl反应平滑地转化为各种完全融合的PAHs。此外，菲丙烯取代的芳基的反应是区域选择性的。调查结果启发了一种快速高效地合成聚苯苯苯衍生物。这项研究不仅允许转化苯基三氟韧剂，而且还公开了对PAHS，特别是聚苯苯乙烯的新逆转态策略。</ 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16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=Uryu Mizuho&option=202" target="_blank" rel="nofollow">Uryu Mizuho;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hiraga Taito&option=202" target="_blank" rel="nofollow">Hiraga Taito;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Koga Yoshito&option=202" target="_blank" rel="nofollow">Koga Yoshito;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Saito Yutaro&option=202" target="_blank" rel="nofollow">Saito Yutaro;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Murakami Kei&option=202" target="_blank" rel="nofollow">Murakami Kei;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Itami Kenichiro&option=202" target="_blank" rel="nofollow">Itami Kenichiro;</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>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</p> <p>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</p> <p>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</p> <p>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</p> <p>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</p> <p>Graduate School of ScienceNagoya UniversityChikusa Nagoya 464-8602 Japan;</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=annulations&option=203" rel="nofollow">annulations;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=C?H activation&option=203" rel="nofollow">C?H activation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=fused rings&option=203" rel="nofollow">fused rings;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=palladium&option=203" rel="nofollow">palladium;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=polycycles&option=203" rel="nofollow">polycycles;</a> </p> <div class="translation"> 机译：环化;C？H激活;融合戒指;钯;多环; 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