Regioselective Hydroalkylation and Arylalkylation of Alkynes by Photoredox/Nickel Dual Catalysis: Application and Mechanism

摘要

Abstract >Alkynes are an important class of organic molecules due to their utility as versatile building blocks in synthesis. Although efforts have been devoted to the difunctionalization of alkynes, general and practical strategies for the direct hydroalkylation and alkylarylation of terminal alkynes under mild reaction conditions are less explored. Herein, we report a photoredox/nickel dual‐catalyzed anti‐Markovnikov‐type hydroalkylation of terminal alkynes as well as a one‐pot arylalkylation of alkynes with alkyl carboxylic acids and aryl bromides via a three‐component cross‐coupling. The results indicate that the transformations proceed via a new mechanism involving a single‐electron transfer with subsequent energy‐transfer activation pathways. Moreover, steady‐state and time‐resolved fluorescence‐spectroscopy measurements, density functional theory (DFT) calculations, and wavefunction analysis have been performed to give an insight into the catalytic cycle. </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> > alkynes是一种重要的有机分子，因为它们作为合成中的多功能建筑块。虽然已经致力于炔烃的差异化，但探讨了温和反应条件下的直接羟基烷基化和末端炔烃基烷基芳基的实际策略。在此，我们通过三组分交叉偶联报告末端炔醇末端炔烃和烷基羧酸和芳基溴的一锅芳基烷基化的光毒剂/镍双催化的抗马铃薯烷基化。结果表明，转化通过涉及具有随后的能量转移激活途径的单电子传递的新机制进行。此外，已经进行了稳态和时间分辨的荧光 - 光谱测量，密度泛函理论（DFT）计算和波消渡函数分析，以欣赏到催化循环。</ 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14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"> </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"> </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=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=arylalkylation&option=203" rel="nofollow">arylalkylation;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=DFT calculations&option=203" rel="nofollow">DFT calculations;</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=nickel&option=203" rel="nofollow">nickel;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photoredox reactions&option=203" rel="nofollow">photoredox reactions;</a> </p> <div class="translation"> 机译：alkynes;芳基烷基;dft计算;羟基烷基;镍;照片ox反应; 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