Difluoroacetaldehyde N‐Triftosylhydrazone (DFHZ‐Tfs) as a Bench‐Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane

Ning Yongquan; Zhang Xinyu; Gai Yi; Dong Yuanqing; Sivaguru Paramasivam; Wang Yingying; Reddy Bhoomireddy Rajendra Prasad; Zanoni Giuseppe; Bi Xihe

摘要

Abstract > Despite the growing importance of volatile functionalized diazoalkanes in organic synthesis, their safe generation and utilization remain a formidable challenge because of their difficult handling along with storage and security issues. In this study, we developed a bench‐stable difluoroacetaldehyde N ‐triftosylhydrazone (DFHZ‐Tfs) as an operationally safe diazo surrogate that can release in?situ two low‐molecular‐weight diazoalkanes, diazoacetaldehyde (CHOCHN <sub>2</sub> ) or difluorodiazoethane (CF <sub>2</sub> HCHN <sub>2</sub> ), in a controlled fashion under specific conditions. DFHZ‐Tfs has been successfully employed in the Fe‐catalyzed cyclopropanation and Doyle–Kirmse reactions, thus highlighting the synthetic utility of DFHZ‐Tfs in the efficient construction of molecule frameworks containing CHO or CF <sub>2</sub> H groups. Moreover, the reaction mechanism for the generation of CHOCHN <sub>2</sub> from CF <sub>2</sub> HCHN <sub>2</sub> was elucidated by density functional theory (DFT) calculations. </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> > 尽管有机合成中挥发性官能化的二氮杂烷烃的重要性越来越重要，但它们的安全生成和利用率仍然是一个强大的挑战，因为它们与储存和安全问题难以处理。在这项研究中，我们开发了一个稳定的二氟甲甲醛 n </ i> -triftosylydone（DFHz-TFS）作为可操作安全的双氮代替代，可以释放出来的α原位两个低分子量的重氮烷烃，二氮酰甲醛（Chochn <sub> 2 </ sub> ）或二氟二乙醚（CF <sub> 2 </ sub> HCHN. <sub> 2 </ sub> ），在特定条件下以受控的方式。 DFHZ-TFS已成功地在Fe催化的环丙烷和Doyle-Kirmse反应中使用，从而突出了DFHZ-TFS的合成效用在含CHO或CF的分子框架的有效施工中 <sub> 2 </ sub> H组。此外，对Chochn产生的反应机制 <sub> 2 </ sub> 来自CF. <sub> 2 </ sub> HCHN. <sub> 2 </ sub> 被密度泛函理论（DFT）计算阐明。 </ 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9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=Ning Yongquan&option=202" target="_blank" rel="nofollow">Ning Yongquan;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zhang Xinyu&option=202" target="_blank" rel="nofollow">Zhang Xinyu;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Gai Yi&option=202" target="_blank" rel="nofollow">Gai Yi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Dong Yuanqing&option=202" target="_blank" rel="nofollow">Dong Yuanqing;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Sivaguru Paramasivam&option=202" target="_blank" rel="nofollow">Sivaguru Paramasivam;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Wang Yingying&option=202" target="_blank" rel="nofollow">Wang Yingying;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Reddy Bhoomireddy Rajendra Prasad&option=202" target="_blank" rel="nofollow">Reddy Bhoomireddy Rajendra Prasad;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Zanoni Giuseppe&option=202" target="_blank" rel="nofollow">Zanoni Giuseppe;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Bi Xihe&option=202" target="_blank" rel="nofollow">Bi Xihe;</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 ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</p> <p>Department of ChemistryUniversity of PaviaViale Taramelli 12 27100 Pavia Italy;</p> <p>Department of ChemistryNortheast Normal UniversityChangchun 130024 China;</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=cyclopropanation&option=203" rel="nofollow">cyclopropanation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=density functional calculations&option=203" rel="nofollow">density functional calculations;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=diazo compounds&option=203" rel="nofollow">diazo compounds;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=difluoroacetaldehyde N-triftosylhydrazone&option=203" rel="nofollow">difluoroacetaldehyde N-triftosylhydrazone;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Doyle–Kirmse reaction&option=203" rel="nofollow">Doyle–Kirmse reaction;</a> </p> <div class="translation"> 机译：环丙烷;密度函数计算;重氮化合物;二氟甲甲醛N-Triftosylydone;Doyle-Kirmse反应; </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/0704028160707.html">Difluoroacetaldehyde N‐Triftosylhydrazone (DFHZ‐Tfs) as a Bench‐Stable Crystalline Diazo Surrogate for Diazoacetaldehyde and Difluorodiazoethane</a> <b>[J]</b> . <span> <a 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