Iridium‐Catalyzed Silylation of Five‐Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl‐Imidazoline Ligand

Karmel Caleb; Rubel Camille Z.; Kharitonova Elena V.; Hartwig John F.

摘要

Abstract > The steric effects of substituents on five‐membered rings are less pronounced than those on six‐membered rings because of the difference in bond angles. Thus, the regioselectivities of reactions of five‐membered heteroarenes that occur with selectivities dictated by steric effects, such as the borylation of C?H bonds, have been poor in many cases. We report that the silylation of five‐membered‐ring heteroarenes occurs with high sterically derived regioselectivity when catalyzed by the combination of [Ir(cod)(OMe)] <sub>2</sub> (cod=1,5‐cyclooctadiene) and a phenanthroline ligand or a new pyridyl‐imidazoline ligand that further increases the regioselectivity. The silylation reactions with these catalysts produce high yields of heteroarylsilanes from functionalization at the most sterically accessible C?H bonds of these rings under conditions that the borylation of C?H bonds with previously reported catalysts formed mixtures of products or products that are unstable. The heteroarylsilane products undergo cross‐coupling reactions and substitution reactions with ipso selectivity to generate heteroarenes that bear halogen, aryl, and perfluoroalkyl substituents. </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> > 由于键角差异，取代基对五元环上的取代基的空间效应比六元环上的偏差不显着。因此，在许多情况下，用空间效应决定的选择性发生的五元杂种物反应的区域选择性，例如C-H键的硼化，在许多情况下差。我们报道，当通过[IR（COD）（OME）]的组合催化时，使用高分子衍生的区域选择性的五元环异质的甲硅烷基化。 <sub> 2 </ sub> （COD = 1,5-环辛二烯）和菲咯啉配体或新的吡啶基 - 咪唑啉配体，其进一步增加了区域选择性。与这些催化剂的甲硅烷基化反应在这些环的条件下，在最常见的CO-H键的条件下，通过先前所报道的催化剂的促进组形成不稳定的产品或产品的混合物，从而在这些环的官能化上产生高产率的杂芳基硅烷烷基。杂芳硅烷产品经历交叉偶联反应和取代反应 ipso </ i> 选择性以产生承载卤素，芳基和全氟烷基取代基的杂戊烷。 </ 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15期</span><b style="margin: 0 2px;">|</b><span>共8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=Karmel Caleb&option=202" target="_blank" rel="nofollow">Karmel Caleb;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Rubel Camille Z.&option=202" target="_blank" rel="nofollow">Rubel Camille Z.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kharitonova Elena V.&option=202" target="_blank" rel="nofollow">Kharitonova Elena V.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hartwig John F.&option=202" target="_blank" rel="nofollow">Hartwig John F.;</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 ChemistryUniversity of CaliforniaBerkeley CA 94720 USA;</p> <p>Department of ChemistryUniversity of CaliforniaBerkeley CA 94720 USA;</p> <p>Department of ChemistryUniversity of CaliforniaBerkeley CA 94720 USA;</p> <p>Department of ChemistryUniversity of CaliforniaBerkeley CA 94720 USA;</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=C?H functionalization&option=203" rel="nofollow">C?H functionalization;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=heteroarenes&option=203" rel="nofollow">heteroarenes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=iridium catalysis&option=203" rel="nofollow">iridium catalysis;</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=silylation&option=203" rel="nofollow">silylation;</a> </p> <div class="translation"> 机译：C？H官能化;杂种酸;铱催化;区域选择性;甜菜碱; </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/0704028162100.html">Iridium‐Catalyzed Silylation of Five‐Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl‐Imidazoline Ligand</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Karmel Caleb&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Karmel Caleb,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Rubel Camille Z.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Rubel Camille Z.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kharitonova Elena V.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Kharitonova Elena V.,</a> <a href="/journal-foreign-19011/" target="_blank" rel="nofollow" class="tuijian_authcolor">Angewandte Chemie .</a> <span>2020</span><span>,第15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：铱催化的五元杂种甲硅烷基化：来自吡啶基 - 咪唑啉配体的高分子衍生的选择性</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_journal-the-american-chemical-society_thesis/0204112959265.html">Iridium-Catalyzed Silylation of C-H Bonds in Unactivated Arenes: A Sterically Encumbered Phenanthroline Ligand Accelerates Catalysis</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Karmel Caleb&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Karmel Caleb,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Chen Zhewei&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Chen Zhewei,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hartwig John F.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Hartwig John F. </a> <a href="/journal-foreign-719/" target="_blank" rel="nofollow" class="tuijian_authcolor">Journal of the American Chemical Society .</a> <span>2019</span><span>,第17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：铱催化未活化芳烃中C-H键的甲硅烷基化：位阻菲咯啉配体会加速催化作用</span> </p> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/academic-journal-foreign_journal-the-american-chemical-society_thesis/0204120183073.html">Iridium-Catalyzed Silylation of C-H 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<span>机译：铱催化在未致死的植物中的C-H键的甲硅烷基化：空间上的菲咯啉配体加速催化</span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/academic-conference-foreign_meeting-252588_thesis/0705015633274.html">Regies elective Aromatic C-H Silylation of Heteroarenes with Fluorodisilanes Catalyzed by Iridium(I) Complexes</a> <b>[C]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yukihiro Nishio&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Yukihiro Nishio,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kazuaki Sato&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Kazuaki Sato,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Takeaki Saiki&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Takeaki Saiki,</a> <a href="/conference-foreign-252588/" target="_blank" rel="nofollow" class="tuijian_authcolor">Symposium on Organometallic Chemistry .</a> 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Multicatalysis: Development of a Bismuth(III) triflate-catalyzed Nucleophilic addition/ Hydrofunctionalization Reaction in the Synthesis of Complex Heterocycles II. C--H Arylation of Arenes and Heteroarenes with Palladium-Carboxylate Catalysts: Identification of the Catalyst Resting State and the Crucial Role of Pivalate Ligand in Stabilization of the Catalyst III. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Importance of Phosphine Ligand for Basic Heteroarene Substrates IV. C--H Arylation of Heteroarenes with Palladium-Carboxylate Catalysts: Effect of the Properties of Basic Heteroarene Substrates on Direct Arylations.</a> <b>[D] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tundel, Rachel E.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Tundel, Rachel E. </a> <span>2011</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：I.多催化作用：在复杂的杂环化合物的合成中三氟甲磺酸铋（III）催化的亲核加成/加氢官能化反应的发展。羰基钯催化剂对芳烃和杂芳烃的CH-H芳基化反应：催化剂静止状态的鉴定以及新戊酸酯配体在稳定催化剂中的关键作用III。羰基钯催化剂催化杂芳烃的CH芳基化：膦配体对基础杂芳烃基质的重要性IV。杂芳烃与钯-羧酸酯的CH芳基化：碱性杂芳烃底物性能对直接芳基化的影响。</span> </p> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-journal-foreign-pmc_detail_thesis/040006052353.html">Efficient Iridium-catalyzed C-H Functionalization/Silylation of Heteroarenes</a> <b>[O] </b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dr. Biao Lu&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Dr. Biao Lu,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Prof. J. 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COMPLEXES WITH STERICALLY DEMANDING LIGANDS</a> <b>[P]</b> . <span> 外国专利：  WO2009073246A1 </span> <span> . 2009-06-11</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：具有立体要求的配位体的铱（III）配合物的合成方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130475028156.html">Rhodium, iridium or cobalt complexes - with substd. phenanthroline or bi:pyridyl ligand, useful as shift conversion catalyst</a> <b>[P]</b> . <span> 外国专利：  FR2515064A1 </span> <span> . 1983-04-29</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：铑，铱或钴配合物-含。菲咯啉或联吡啶基配体，用作转化催化剂 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130411028652.html">PHOSPHORUS LIGANDS AND METHOD FOR THE SELECTIVE 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