Hydroarylation of 2‐Aryloxybut‐1‐en‐3‐ynes via Pd/Acid‐Catalyzed C?H Bond Activation: A Concise Synthesis of 2,3‐Bismethylene‐2,3‐dihydrobenzofurans

Minami Yasunori; Sakai Megumi; Sakamaki Takumi; Hiyama Tamejiro

摘要

Abstract > An intramolecular exo ‐hydroarylation of 2‐aryloxy‐1,4‐disilylbut‐1‐en‐3‐ynes via ortho ‐C?H bond activation under palladium(0) and acid catalysis was found to give 2,3‐bis(silylmethylidene)‐2,3‐dihydrobenzofurans. The two silyl groups present probably promoted the reaction and played a key role in stabilizing the diene moiety in the product. The products readily led to functionalized condensed cycles by a Diels–Alder reaction. </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 XMLNS =“http://www.wiley.com/namespaces/wiley”type =“main”xml：lang =“en”> <title type =“main”>抽象</ title> >分子内通过钯（0）和酸下，通过邻-cα-H键活化的2-芳基氧基-1,4-insilylbut-1-en-3-ynes-1-en-3-ynes-1-en-3-ynes的羟基芳基。发现催化得到2,3-双（甲硅烷甲基）-2,3-二氢苯并呋喃。存在的两种甲硅烷基组可能促进反应并在稳定产物中的二烯部分进行了关键作用。产品容易通过Diels-Alder反应导致官能化的凝聚循环。 </ p> </ abstract> </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-16161/'>《Chemistry, an Asian journal》</a> <b style="margin: 0 2px;">|</b><span>2017年第18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=Minami Yasunori&option=202" target="_blank" rel="nofollow">Minami Yasunori;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sakai Megumi&option=202" target="_blank" rel="nofollow">Sakai Megumi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sakamaki Takumi&option=202" target="_blank" rel="nofollow">Sakamaki Takumi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hiyama Tamejiro&option=202" target="_blank" rel="nofollow">Hiyama Tamejiro;</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>Research and Development InitiativeChuo University1-13-27 Kasuga Bunkyo-ku Tokyo 112-8551 Japan;</p> <p>Department of Applied ChemistryChuo University1-13-27 Kasuga Bunkyo-ku Tokyo 112-8551 Japan;</p> <p>Department of Applied ChemistryChuo University1-13-27 Kasuga Bunkyo-ku Tokyo 112-8551 Japan;</p> <p>Research and Development InitiativeChuo University1-13-27 Kasuga Bunkyo-ku Tokyo 112-8551 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/159.html" title="化学">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=alkynes&option=203" rel="nofollow">alkynes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cycloaddition&option=203" rel="nofollow">cycloaddition;</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=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=synthetic methods&option=203" rel="nofollow">synthetic methods;</a> </p> <div class="translation"> 机译：alkynes;环加成;c？h激活;钯;合成方法; 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class="tuijian_auth tuijian_authcolor"> . 骆文博</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=梅其炳&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,梅其炳</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张生勇&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,张生勇</a> <span> <a href="/journal-cn-6586/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第四军医大学学报 </a> </span> <span> . 1995</span><span>,第4期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-25149_thesis/020221320019.html">2,7-二甲基-2,3-二氢-6-氯苯并呋喃的分析方法</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张红芬&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张红芬</a> <span> <a href="/conference-cn-25149/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国化工学会农药专业委员会第十二届年会 </a> <span> <span> . 2005</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312575181.html">2,2-二甲基-5-酰基-2,3-二氢苯并呋喃衍生物的合成与生物活性</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李婉&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 李婉</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120105236142.html">2－呋喃甲酰基－3－芳基－4－乙氧基甲酰基－5－甲基－反式－2,3－二氢呋喃及其制备方法</a> <b>[P]</b> . <span> 中国专利： CN101037425A </span> <span> . 2007-09-19</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120104252500.html">合成5-酰氧基和5-烷氧基-2，3-二氢-4，6，7-三甲基-2-(RS)-苯并呋喃乙酸的新方法</a> <b>[P]</b> . <span> 中国专利： CN1054767A </span> <span> . 1991-09-25</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130443572475.html">MONOARGININYL SALT OF (E) -3- 1-N-BUTYL-5 - (2- (2-CARBOXYPHENYL) METHOXY-4-CHLORPHENYL -1H-PYRAZOL-4-YL -2 - (5-METHOXY- 2,3-DIHYDROBENZOFURAN-6-YL) METHYL -PROP-2-EN CARBONIC ACID</a> <b>[P]</b> . <span> 外国专利：  DE69807745T2 </span> <span> . 2003-05-15</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：（E）-3- [1-N-丁基-5-[（2-（2-羧苯基）甲氧基-4-氯苯基] -1H-吡唑-4-基]的单萘醌盐-2-[（5-甲氧基-2,3-二氢联苯并呋喃-6-基）[甲基] -PROP-2-EN碳酸 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130409373329.html">ENATIOPURE SYNTHESIS OF INDOLIZINOINDOLE ALKALOID (+) HARMICINE AND (-) HARMICINE FROM (2S,3R)-TETRAHYDRO-3-HYDROXY-5-OXO-2,3-FURANDICARBOXYLIC ACID (HIBISCUS ACID) AND (2S,3S)-TETRAHYDRO-3-HYDROXY-5-OXO-2,3-FURANDICARBOXYLIC ACID (GARCINIA ACID)</a> <b>[P]</b> . <span> 外国专利：  IN2015CH03682A </span> <span> . 2017-01-20</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：从（2S，3R）-四氢-3-羟基-5-OXO-2,3-呋喃二甲酸（水BI酸）和（2S，3S）-四氢-（-）和（2），3R）-四氢萘酚对映体合成吲哚并吲哚碱3-HYDROXY-5-OXO-2,3-FURANDICARBOXYAL ACID（GARCINIA ACID） </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130461429607.html">METHOD OF SYNTHESIS OF 2,3-DIOXO-1,10@ - DIPHENYL - 2,3 - DIHYDRO - 1H - PYRROLO - 2,3-B 1,5 BENZOTHIAZEPINE - 4 - CARBOXYLIC ACID ISOPROPYL ESTER</a> <b>[P]</b> . <span> 外国专利：  SU01810345A1 </span> <span> . 1993-04-23</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：合成2,3-二氧杂-1,10 @-二苯基-2,3-二氢-1H-吡咯-[2,3-B] [1,5]苯并噻嗪-4-羧酸异丙烯酯的方法 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: 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