Visible‐Light‐Driven Strain‐Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters

Davenport Raffael; Silvi Mattia; Noble Adam; Hosni Zied; Fey Natalie; Aggarwal Varinder K.

摘要

Abstract >There are a limited number of ring‐contraction methodologies which convert readily available five‐membered rings into strained four‐membered rings. Here we report a photo‐induced radical‐mediated ring contraction of five‐membered‐ring alkenyl boronate complexes into cyclobutanes. The process involves the addition of an electrophilic radical to the electron‐rich alkenyl boronate complex, leading to an α‐boryl radical. Upon one‐electron oxidation, ring‐contractive 1,2‐metalate rearrangement occurs to give a cyclobutyl boronic ester. A range of radical precursors and vinyl boronates can be employed, and chiral cyclobutanes can be accessed with high levels of stereocontrol. The process was extended to the preparation of benzofused cyclobutenes and the versatility of the boronic ester was demonstrated by conversion to other functional groups. </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> >有有限数量的环收缩方法，其将易于获得的五元环转化为紧张的四元环。在这里，我们将5元环链环硼酸酯复合物的光学诱导的自由基介导的环收缩分成环丁烷。该方法涉及向电子富含电子的链烯基硼酸酯复合物中加入电泳基团，导致α-骨骼基团。在单电子氧化时，发生环形1,2-金属重排，得到环丁基硼酸酯。可以采用一系列自由基前体和乙烯基硼酸盐，并且可以使用高水平的立体丁烷进行手性环丁烷。该方法延伸至苯并稠合的环丁烯的制备，并通过转化为其他官能团来证明硼膦酯的多功能性。</ 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=Davenport Raffael&option=202" target="_blank" rel="nofollow">Davenport Raffael;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Silvi Mattia&option=202" target="_blank" rel="nofollow">Silvi Mattia;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Noble Adam&option=202" target="_blank" rel="nofollow">Noble Adam;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Hosni Zied&option=202" target="_blank" rel="nofollow">Hosni Zied;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Fey Natalie&option=202" target="_blank" rel="nofollow">Fey Natalie;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Aggarwal Varinder K.&option=202" target="_blank" rel="nofollow">Aggarwal Varinder K.;</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>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</p> <p>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</p> <p>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</p> <p>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</p> <p>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</p> <p>School of ChemistryUniversity of BristolCantock's Close Bristol BS8 1TS UK;</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=Boron chemistry&option=203" rel="nofollow">Boron chemistry;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Cyclobutanes&option=203" rel="nofollow">Cyclobutanes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Metalate rearrangement&option=203" rel="nofollow">Metalate rearrangement;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Photoredox catalysis&option=203" rel="nofollow">Photoredox catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ring contraction&option=203" rel="nofollow">Ring contraction;</a> </p> <div class="translation"> 机译：硼化学;环丁酸;金属重排;Photoreox催化;戒指收缩; </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/0704028161875.html">Back Cover: Visible‐Light‐Driven Strain‐Increase Ring Contraction Allows the Synthesis of Cyclobutyl Boronic Esters (Angew. 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href="/conference-cn-2532/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国超声医学工程学会第十二届全国超声心动图学术会议 </a> <span> <span> . 2014</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020314859045.html">三尖瓣环收缩期位移与右室应变定量评价肺动脉高压患者右室收缩功能</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=金鑫焱&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 金鑫焱</a> <span> . 2015</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120104618931.html">1－1－(4－氯苯基)环丁基－3－甲基丁基胺的合成方法</a> <b>[P]</b> . <span> 中国专利： CN1415597A </span> <span> . 2003-05-07</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120105064865.html">多环稠环型π共轭有机材料、其合成中间体、多环稠环型π共轭有机材料的制备方法、以及多环稠环型π共轭有机材料的合成中间体的制备方法</a> <b>[P]</b> . <span> 中国专利： CN1875024A </span> <span> . 2006-12-06</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130403444324.html">SYNTHESIS METHOD FOR BORONIC ACID ESTER COMPOUND, AND SODIUM SALT OF BORONIC ACID ESTER COMPOUND AND SYNTHESIS METHOD THEREFOR</a> <b>[P]</b> . <span> 外国专利：  WO2019142854A1 </span> <span> . 2019-07-25</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：硼酸酯化合物的合成方法，硼酸酯化合物的钠盐及其合成方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130442436070.html">Association of Bifidobacterium longum var. animalis and Lactobacillus acidophilus strains - producers of vitamins B1, B2 and B3 (57) The invention refers to microbiology and may be used in obtaining curativoprophylactic preparations, used for increasing the level of synthesis of the vitamins of B group in the digestive tract. The association of Bifidobacterium longum var. animalis CNM Bl-527 and Lactobacillus acidophilus CNM La-417 strains possesses the capacity to synthesize vitamins of B group, namely the vitamins B1, B2 and B3. The result of the invention consists in increasing the level of synthesis of the vitamins B1, B2 and B3 by the obligate microorganisms of the digestive tract. Claims: 1</a> <b>[P]</b> . <span> 外国专利：  MD2527B2 </span> <span> . 2004-08-31</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：长双歧杆菌协会动物群和嗜酸乳杆菌菌株-维生素B1，B2和B3的生产者（57）本发明涉及微生物学，可以用于获得预防性治疗的制剂，用于提高消化道中B组维生素的合成水平。长双歧杆菌协会。动物性CNM Bl-527和嗜酸乳杆菌CNM La-417菌株具有合成B组维生素（即维生素B1，B2和B3）的能力。本发明的结果在于通过消化道的专性微生物提高维生素B1，B2和B3的合成水平。索赔：1 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130415474533.html">Method of shielding ultraviolet light and increasing visible light, and ultraviolet-light-shielding and visible-light-increasing material which enables implementation of the method</a> <b>[P]</b> . <span> 外国专利：  US9140836B2 </span> <span> . 2015-09-22</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> 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