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class="dhr_mt1">推薦丨鎳催化多組分連續還原偶聯反應</h1> <span class="dhr_mt2">發表時間：2022-07-19</span> <div class="dhr_mt3"> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;text-align:justify;background-color:#FFFFFF;text-indent:2em;"> <span style="font-size:15px;color:#3E3F3E;"><img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113003246.jpg" alt="" /><br /> </span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;text-align:justify;background-color:#FFFFFF;text-indent:2em;"> <span style="font-size:15px;color:#3E3F3E;">近年來，還原偶聯反應成為構建有機分子的有效策略。這類反應中涉及兩種不同的親電試劑參與反應，并且大部分反應被認為Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>I</sup></span><span style="font-size:15px;color:#3E3F3E;">物種為反應的催化活性物種（Figure 1A）。2019年，胡喜樂課題組報道了鎳催化烷基鹵化物與氯甲酸酯的還原偶聯反應，該反應涉及Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>0</sup></span><span style="font-size:15px;color:#3E3F3E;">物種與氯甲酸酯發生氧化加成形成Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">物種（Figure 1B）?；谇叭说墓ぷ?，最近，<strong>阿卜杜拉國王科技大學（KAUST）Chen Zhu和Magnus Rueping課題組</strong>實現了具有挑戰性的鎳催化芳基鹵化物、烷基鹵化物和氯甲酸乙酯的三組分還原偶聯反應。此反應利用氯甲酸乙酯作為簡單易得的CO源，實現了多種芳基烷基酮的合成。相關成果發表在<em>Angew. Chem. Int. Ed.</em>, <strong>2022</strong>,<em> </em>DOI: 10.1002/anie.202204144上（Figure 1C）。</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;"><img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113101334.jpg" alt="" />（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;text-align:justify;background-color:#FFFFFF;text-indent:2em;"> <span style="font-size:15px;color:#3E3F3E;">由于此轉化包含三種不同的親電試劑參與反應，因此高化學選擇性地識別各組分的反應活性具有一定的挑戰。為了更深入理解此反應的活化模式和反應細節，作者首先進行了DFT計算（Figure 2）?；谟嬎憬Y果，作者提出了此反應可能的催化循環：首先Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">被Zn還原成Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>0</sup></span><span style="font-size:15px;color:#3E3F3E;">；隨后Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>0</sup></span><span style="font-size:15px;color:#3E3F3E;">與Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">發生歸中得到Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>I</sup></span><span style="font-size:15px;color:#3E3F3E;">中間體<strong>A</strong>；接著<strong>A</strong>與芳基鹵化物發生氧化加成，并與另一個Ni<sup>I</sup>中間體<strong>A</strong>發生歸中得到Ar-Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">-I中間體<strong>B1</strong>；此外，芳基碘化物還可以和Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>0</sup></span><span style="font-size:15px;color:#3E3F3E;">直接發生氧化加成得到中間體<strong>B1</strong>；接著<strong>B1</strong>可以被Zn還原為Ar-Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>I</sup></span><span style="font-size:15px;color:#3E3F3E;">中間體<strong>C</strong>；<strong>C</strong>可以與氯甲酸乙酯發生氧化加成得到Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>III</sup></span><span style="font-size:15px;color:#3E3F3E;">中間體<strong>D1</strong>，然后被Zn還原為Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">中間體<strong>F</strong>；隨著OEt基團發生遷移，得到新的Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>II</sup></span><span style="font-size:15px;color:#3E3F3E;">中間體<strong>G</strong>，并進一步被Zn還原為Ar-Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>I</sup></span><span style="font-size:15px;color:#3E3F3E;">-CO中間體<strong>H</strong>；接著中間體<strong>H</strong>與烷基溴化物發生反應得到烷基自由基和中間體<strong>I1</strong>；<strong>I1</strong>發生CO遷移得到關鍵的?；囍虚g體<strong>J</strong>；接著<strong>J</strong>被烷基自由基捕獲得到烷基-Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>III</sup></span><span style="font-size:15px;color:#3E3F3E;">-?；虚g體<strong>K</strong>，而后<strong>K</strong>經歷還原消除得到產物并再生Ni</span><span style="color:#3E3F3E;font-size:12px;"><sup>I</sup></span><span style="font-size:15px;color:#3E3F3E;">物種（Figure 3）。</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113103432.jpg" alt="" /> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;">（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;"><img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113200412.jpg" alt="" />（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;text-align:justify;background-color:#FFFFFF;text-indent:2em;"> <span style="font-size:15px;color:#3E3F3E;">在推測了可能的反應機理后，作者以1-溴-3-苯基丙烷<strong>1</strong>、氯甲酸乙酯<strong>2</strong>和4-碘苯甲酸甲酯<strong>3a</strong>作為模板底物進行條件篩選（Table 1）。當反應使用NiI</span><span style="color:#3E3F3E;font-size:12px;"><sub>2</sub></span><span style="font-size:15px;color:#3E3F3E;">作為催化劑，1,10-鄰菲啰啉作為配體, Zn作為還原劑，MgCl</span><span style="color:#3E3F3E;font-size:12px;"><sub>2</sub></span><span style="font-size:15px;color:#3E3F3E;">作為添加劑，DMA為溶劑，室溫下反應12 h，可以以77%的產率得到相應的產物<strong>4a</strong>（Table 1，entry 1）。</span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;"><img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113202513.jpg" alt="" />（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <span style="font-size:15px;color:#3E3F3E;">隨后，作者嘗試對此合成方法的底物范圍進行探索（Figure 4）。首先作者對芳基碘化物的底物適應性進行嘗試，實驗結果表明反應具有較好的底物適應性（Figure 4a）。除此之外，反應對一系列不同取代的一級或二級烷基鹵化物也具有較好的底物適應性。并且可以兼容諸如烯基、鹵素、氰基、酯基、醚等不同官能團，表明此轉化具有較好的官能團兼容性（Figure 4b）。遺憾的是，三級烷基鹵化物并不能有效地參與此反應，只能得到痕量的相應產物。</span> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113204058.jpg" alt="" /> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;">（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <span style="font-size:15px;">最后，為了進一步探索反應機理，作者進行了一系列控制實驗（Figure 5）。當反應中利用有機鋅試劑替代烷基鹵化物反應時并沒有得到相應的產物，說明產物酮的形成過程并沒有涉及有機鋅試劑的形成（Figure 5a）。當反應中加入自由基捕獲劑TEMPO時，反應被完全抑制，并以37%的產率觀察到了自由基捕獲產物<strong>32</strong>（Figure 5b）。當使用溴乙基環丙烷<strong>33</strong>參與反應時也沒有得到相應的產物酮，而是得到了開環產物<strong>20</strong>（Figure 5c）。當使用串聯烯烴的烷基溴化物作為底物時，可以以30%的產率得到相應的環化偶聯產物<strong>35</strong>（Figure 5d）。上述實驗均可以證明反應中包含烷基自由基中間體。</span><br /> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;"><img src="https://imgcn6.guidechem.com/img/product/2022/7/19/212942113205887.jpg" alt="" /><br /> </span> </p> <p style="color:#222222;font-family:system-ui, -apple-system, BlinkMacSystemFont, "font-size:17px;background-color:#FFFFFF;text-align:center;"> <span style="font-size:14px;">（圖片來源：</span><em><span style="font-size:14px;">Angew. Chem. Int. Ed.</span></em><span style="font-size:14px;">）</span> </p> <span style="font-size:15px;color:#3E3F3E;"><strong>總結：阿卜杜拉國王科技大學（KAUST）Chen Zhu和Magnus Rueping課題組</strong>利用鎳催化的還原羰基化策略，使用芳基鹵化物、烷基鹵化物和氯甲酸乙酯作為起始原料，實現多種芳基烷基酮的合成。氯甲酸乙酯可以作為簡單易得的CO源應用到反應中。此反應顯示出較好的官能團耐受性和底物兼容性。DFT計算和控制實驗為反應機理的提出提供了理論依據。</span><span style="color:#7F7F7F;font-size:14px;">文獻：</span><span style="color:#7F7F7F;font-size:14px;"><span style="font-family:-apple-system, BlinkMacSystemFont, Arial, sans-serif;">https://onlinelibrary.wiley.com/doi/10.1002/anie.202204144</span></span> <p> <br /> </p> <span><span style="color:#888888;font-size:12px;">版權聲明：本文轉自</span><span style="color:#888888;font-size:14px;">有機光電前沿</span><span style="color:#888888;font-size:12px;">，如不希望被轉載的媒體或個人可與我們聯系，我們將立即刪除</span></span> </div> <div class="pge_re"> <span>上一篇：<a href="/news/show514482.html">可接定制，穩定供應，四苯乙烯類衍生物，MOF,COF配體，歡迎咨詢采購??！</a></span> <span>下一篇：無</span> </div> <style type="text/css"> .news_tag{margin-top:10px;} 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