Switch in Selectivity for Formal Hydroalkylation of 1,3‐Dienes and Enynes with Simple Hydrazones

Lv Leiyang; Yu Lin; Qiu Zihang; Li Chao‐Jun

摘要

Abstract >Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio‐enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2‐Markovnikov hydroalkylation of 1,3‐dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti‐Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro‐metallation across the metal‐π‐allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3‐enynes. </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> >控制反应选择性是对化学家的永久追求。区域选择性催化，利用和/或克服了先天的空间和电子偏差，以从相同的起始材料提供不同的富集产品，代表了具有不同合成的强大工具。最近，据报道，当使用镍催化剂时，据报道，1,3-二烯的1,2- Markovnikov羟甲基烷基化含有简单的含有氮的含腙。当使用镍催化剂时产生支链烯丙基化合物。作为努力的一部分，这里显示的是通过改变钌催化剂来获得Markovnikov的完整开关，从而通过改变钌催化剂来获得专门的直接和有效地进入同性恋产品。同位素取代实验表明，在钌催化下，在金属-π-烯丙基系统上没有可逆水解金属。此外，该方案适用于1,3- inynes的远端C = C键的再生羟甲基化。</ 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7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=Lv Leiyang&option=202" target="_blank" rel="nofollow">Lv Leiyang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yu Lin&option=202" target="_blank" rel="nofollow">Yu Lin;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Qiu Zihang&option=202" target="_blank" rel="nofollow">Qiu Zihang;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Li Chao‐Jun&option=202" target="_blank" rel="nofollow">Li Chao‐Jun;</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 Chemistry and FRQNT Center for Green Chemistry and CatalysisMcGill University801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada;</p> <p>Department of Chemistry and FRQNT Center for Green Chemistry and CatalysisMcGill University801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada;</p> <p>Department of Chemistry and FRQNT Center for Green Chemistry and CatalysisMcGill University801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada;</p> <p>Department of Chemistry and FRQNT Center for Green Chemistry and CatalysisMcGill University801 Sherbrooke Street West Montreal Quebec H3A 0B8 Canada;</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=dienes&option=203" rel="nofollow">dienes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydrazones&option=203" rel="nofollow">hydrazones;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=hydroalkylation&option=203" rel="nofollow">hydroalkylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=regioselectivity&option=203" rel="nofollow">regioselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ruthenium&option=203" rel="nofollow">ruthenium;</a> </p> <div class="translation"> 机译：二烯;腙;氢烷基化;区域选择性;钌; </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/0704028161248.html">Switch in Selectivity for Formal Hydroalkylation of 1,3‐Dienes and Enynes with Simple Hydrazones</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Lv Leiyang&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Lv Leiyang,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yu Lin&option=202" target="_blank" rel="nofollow" class="tuijian_auth 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</li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120515919.html">从1,4－二卤代－1,4－二(三甲基硅基)－1,3－丁二烯衍生物制备1,1,4,4－四卤代－1,3－丁二烯衍生物的方法</a> <b>[P]</b> . <span> 中国专利： CN100526272C </span> <span> . 2009.08.12</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130430409783.html">process for decreasing odor emission from dispersions of vinyl aromatic 1,3-diene copolymers stabilized with aqueous protective colloids, dispersions of 1,3-diene vinyl aromatic copolymers and powder redispersion Based on 1,3-diene copolymers vinyl aromatic diene and its application.</a> <b>[P]</b> . <span> 外国专利：  BR9915459B1 </span> <span> . 2008-11-18</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：降低由含水保护胶体稳定的乙烯基芳族1,3-二烯共聚物的分散体，1,3-二烯乙烯基芳族共聚物的分散体和基于1,3-二烯共聚物乙烯基芳族二烯的粉末再分散的气味排放的方法。 </span> </p> </li> <li> <div> <b>4. </b><a 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