Name: mizoroki-heck cross-coupling reactions catalyzed by dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium under mild reaction conditions
Uploaded: 2014-03-20T19:00:00
Duration: 11 min 44 s
Description: Watch this Scientific Journal Video about Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions at JoVE.com

通过应用科学苏黎世大学以及瑞士国家科学基金会（SNSF）的财政支持是公认的。

1。配位体合成（1,1&#39;，1&#39;&#39; - （Phosphinetriyl）tripiperidine） <ol><li>加入150毫升无水乙醚中，在烘箱干燥的500ml园底烧瓶中5毫升三氯化磷（57.3毫摩尔）。把搅拌棒的圆底烧瓶中，并附加250毫升滴液漏斗，盖上隔烧瓶。 </li><li>冷却该溶液至0℃，通过将圆底烧瓶在冰浴中。 </li><li>制备42.5毫升哌啶中的溶液（429.8毫摩尔，7.5当量相对。到的PCl 3）和100毫升乙醚，并缓慢地通过滴液漏斗中加入该溶液中放入搅拌的乙醚溶液，含有三氯化磷。哌啶除了伴随着的哌啶氯化物沉淀。 </li><li>加完后，升温反应混合物至室温。为了确保全面转换，搅拌30分钟在室温的解决方案。 </li><li>过滤该反应混合物通过玻璃料和收集在500毫升的滤液圆底烧瓶中。为了增加1,1收率&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine用另外100ml无水乙醚洗涤滤饼。 </li><li>蒸发用旋转蒸发器将滤液的溶剂，以获得纯配位体（1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine）在&gt; 80％产率，为灰白色油状物，其固化以时间。检查产品纯度用31 P {1 H} NMR光谱（δ在117.3 ppm的在C 6 D 6）8a 上 。 </li></ol> 2。催化剂的合成（二氯{双[1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine]}钯） <ol><li>称出[加入Pd（COD）Cl 2中]（0.35毫摩尔，100毫克），加入到一个干净的，烘箱干燥的50ml圆底含10毫升无水THF的烧瓶中。添加搅拌棒，盖上隔膜烧瓶中，搅拌悬浮液。 </li><li>称取1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine（0.875毫摩尔，248毫克），并加入到含有1干净，干燥的小瓶0毫升无水THF。用注射器通过隔膜的THF悬浮液[加入Pd（COD）Cl 2中]的（phosphinetriyl）tripiperidine溶液-添加1,1&#39;，1&#39;&#39;。该悬浮液立即变成而另外一个暗黄色溶液，这表明反应完成。 </li><li>为了除去不溶性固体迅速传递反应混合物经烘箱干燥的玻璃料和在25毫升圆底烧瓶中收集滤液。在减压下除去挥发物。用5ml戊烷洗涤钯络合物三次。 </li><li>用倾析法除去戊烷。干燥，减压黄色粉末，定量得到分析纯的钯配合物[（P（C 5 H 10 N 3）3）2中PdCl 2]（1）。检查1纯度用31 P {1 H} NMR谱（δ92.5 ppm的在C 6 D 6）30。 </li></ol> 3。哎呀雷阿CTION由[（P（C 5 H 10 N）3）2氯化钯2]催化（1） <ol><li>重量出[（P（C 5 H 10 N 3）3）2中PdCl 2]（0.05毫摩尔，37.15毫克），并加入到烘箱干燥的25毫升的Schlenk。覆盖舒伦克有隔膜;疏散Schlenk，并回填与二氮。加入10毫升干燥并经注射器通过隔膜加入到烧瓶中脱气的THF中。 </li><li>重出四丁基溴化铵（1.0毫摩尔，322.4毫克）和碳酸钾（20毫摩尔，2.77克），将它们添加在清洁，烘干25毫升圆底Schlenk烧瓶中。通过注射器加入20毫升N-甲基-2 -吡咯烷酮（NMP）的进入的Schlenk烧瓶中，36，37。添加搅拌棒和覆盖隔烧瓶。疏散和回填Schlenk烧瓶与二氮。 </li><li>溶解1 - 溴-4 - 苯氧基苯（10毫摩尔，1.75毫升）和苯乙烯（15毫摩尔，1.72毫升）在5毫升NMP中，并通过注射器加入该溶液中放入Schlenk烧瓶中。一通过应用二氮流ttach回流冷凝器。连接回流冷凝器的油鼓泡器，并设置二氮的轻微过压。 </li><li>加热反应液至100℃并搅拌5分钟在此温度下该溶液中。将催化剂溶液（0.05摩尔％，0.005毫摩尔，1毫升THF中）加至经注射器热的反应混合物中，并剧烈搅拌，针对所指示的时间（3小时在这个例子中）。通过GC / MS检查产品的形成。 </li><li>从油浴中取出的Schlenk，将反应混合物暴露于空气和淬火用50毫升1M盐酸。加入冷却的反应混合物倒入500毫升的分液漏斗中，并加入乙酸乙酯（50毫升）中。通过萃取分离哎呀产品，并结合所有的有机相在锥形瓶中。添加硫酸镁浸泡了水存在的任何最后一笔款项在溶液中。 </li><li>过滤过的纸过滤合并的有机层到圆底烧瓶中。与ADDIT洗涤滤饼有理50ml乙酸乙酯。集中在旋转蒸发器的溶液中，得到的粗偶联产物。 </li><li>通过柱色谱法，使用己烷和的混合物二乙醚（5:1）作为洗脱剂分离的Heck产物。使溶剂蒸发在旋转蒸发器。通过1 H和13 C {1 H} NMR谱35检查产品纯度。 </li></ol>

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A New Mechanism When Hydrogen Is the Reductant: Slow, Continuous Nucleation and Fast Autocatalytic Surface Growth.</a> J. Am. Chem. Soc. 119, 10382-10400 (1997).</li><li>Widegren, J. A., Bennett, M. A., Finke, R. G. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=Is+It+Homogeneous+or+Heterogeneous+Catalysis?+Identification+of+Bulk+Ruthenium+Metal+as+the+True+Catalyst+in+Benzene+Hydrogenations+Starting+with+the+Monometallic+Precursor,+Ru(II)(&#951;6-C6Me6)(OAc)2,+Plus+Kinetic+Characterization+of+the+Heterogeneous+Nucleation,+Then+Autocatalytic+Surface-Growth+Mechanism+of+Metal+Film+Formation.">Is It Homogeneous or Heterogeneous Catalysis? Identification of Bulk Ruthenium Metal as the True Catalyst in Benzene Hydrogenations Starting with the Monometallic Precursor, Ru(II)(&#951;6-C6Me6)(OAc)2, Plus Kinetic Characterization of the Heterogeneous Nucleation, Then Autocatalytic Surface-Growth Mechanism of Metal Film Formation.</a> 125, 10301-10310 (2003).</li><li>Widegren, J. A., Finke, R. G. <a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed&cmd=Search&doptcmdl=Citation&defaultField=Title+Word&term=A+review+of+the+problem+of+distinguishing+true+homogeneous+catalysis+from+soluble+or+other+metal-particle+heterogeneous+catalysis+under+reducing+conditions.">A review of the problem of distinguishing true homogeneous catalysis from soluble or other metal-particle heterogeneous catalysis under reducing conditions.</a> J. Mol. Catal. A. 198, 317-341 (2003).</li></ol>

作者什么都没有透露。

二氯{双[1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine]}钯（1）是一种非常廉价和容易获得，空气中稳定的高活性催化剂的Heck用在温和的反应，有效地经营一个优秀的官能团耐受性条件干净，得到偶联产物在非常高的产量。的1的优异的催化活性（和一般适用性）是由于aminophosphines的独特性质：在相比其膦基类似物，可比水平的空间体积以及aminophosphines的σ-给体的强度本质上是相同活动中发现的类型[复合物（p {（NC 5 H 10）3 - N （C 6 H 11），n}的 ）2加入Pd（Cl）的2]（其中n = 0-3; 图3）中的交叉偶联反应，其中的分子机制是可操作。另一方面，不稳定的的PN债券aminophosphines（朝向质子灵敏度;在水如的形式）字符提供有效地控制钯纳米粒子的形成的可能性：增加配体的PN键数依次减轻他们的水引起的降解和纳米颗粒从而形成从各自的复合物。因此，由于钯纳米粒子1的催化活性形式在Heck反应35，由S形动力学36,37或添加大量过量的金属汞的芳基溴化物的反应混合物经过有效的抑制催化所示，烯烃和催化剂，例如38，以及它们的检测通过示例性的Heck偶联反应由带有能量色散X射线（EDX）analysator 35的1取代的透射电子显微镜（TEM）的反应混合物的分析，1&#39;，1&#39;&#39; - （phosphinetri基）tripiperidine由1,1&#39; - （cyclohexylphosphinediyl）二哌啶），1 - （dicyclohexylphosphinyl）哌啶），或三环己基膦，其依次增加了复杂的稳定性，因此，可延缓（水引起的）形成的纳米颗粒物的。作为一个结果，而二氯双（1 - （dicyclohexylphosphinyl）哌啶）钯，是选择在140℃进行的Heck反应的催化剂，是对二氯{双[1,1&#39;，获得了最高的催化活性1 &#39;&#39; - （phosphinetriyl）tripiperidine]}钯[（P（NC 5 H 10）3）2的Pd（CL）2]（1）在100℃，该系列中的最稳定的复合物。 <img alt="图5" fo:content-width="6in" fo:src="/files/ftp_upload/51444/51444fig5highres.jpg" src="/files/ftp_upload/51444/51444fig5.jpg" /> 图5。二氯{双（氨基膦）}友谊的配体组合物的效果ladium以[（p {（NC 5 H 10）3通式-不适用 （C 6 H 11），n}的 ）2加入Pd（Cl）的2]（其中n = 0-2）的络合物的稳定性，因此，在（水引起的）纳米颗粒的形成容易，因此，其在温和的催化性能反应条件中的Heck交叉偶联反应。 <a href="https://www.jove.com/files/ftp_upload/51444/51444fig5highres.jpg" target="_blank">点击这里查看大图。</a> 虽然上述合成以及Heck反应协议是直线前进，一些常见的故障排除步骤为：（a）确保该四丁基溴化铵是新购买或妥善保存（四丁基溴化铵具有吸湿性），（二）确保干溶剂用于当制备少量配体的配体的合成，（三）确保1无论是新鲜配制或惰性气氛下储存，（四）确保NMP或DMF是新买的，（五）确保化学品或者是新购买或妥善保存，（六）烘干所有玻璃器皿和凉爽在真空条件下。

钯催化的CC交叉偶联反应，这是由诺贝尔化学奖于2010年12月荣获承认，现在属于一个不可缺少的工具为目标导向合成在所有的研究领域和工业领域复杂的有机分子。例如Mizoroki-Heck反应，使烯烃在碱的存在下芳基卤化物的偶联，是当今最常用的方法为乙烯基苯的制备（ 图1）。 Heck反应已被证实发现在两种广泛效用，天然产物在学术界和合成的药物和农用化学品工业1-10全合成。 <img alt="图1" fo:content-width="6in" fo:src="/files/ftp_upload/51444/51444fig1highres.jpg" SRC="/files/ftp_upload/51444/51444fig1.jpg" /> 图1。一般的Heck交叉偶联反应<html>芳基溴化物与烯烃之间。 <a HREF="https://www.jove.com/files/ftp_upload/51444/51444fig1highres.jpg" TARGET="_blank">点击这里查看大图。</a> 紫杉酚，在癌症化疗中使用的有丝分裂抑制剂，顺尔宁，哮喘药和二甲戊乐灵除草剂以及Cyclotene，单体的高性能电子树脂是已被成功地制备，包括在其合成一个的Heck-Mizoroki交叉偶联步骤的实例（ 图2）11-14。 <img alt="图2" fo:content-width="6in" fo:src="/files/ftp_upload/51444/51444fig2highres.jpg" SRC="/files/ftp_upload/51444/51444fig2.jpg" /> 图2。涉及钯催化的Heck交叉偶联反应中的关键合成步骤工业相关的有机化合物的例子。ghres.jpg“TARGET =”_blank“&gt;点击这里查看大图。 尽管最近的发展已大大增加的Heck的活性催化剂15-29，一个典型的反应协议与芳基溴化物作为底物，仍需要高的反应温度（140℃），在高达1％（摩尔）和反应时间的范围内催化剂负载至24小时。此外，改性反应条件，包括反应温度，催化剂负载量，碱，溶剂和添加剂， 例如经常被报道，这意味着这些协议将很少发现其在有机合成中的应用，由于缺乏通用性。此外，大多数的催化剂需要多个反应步骤，它们的合成，因此，是费时和低产。此外，惰性气氛技术和稳定性差昂贵的起始原料通常用于其制备。这是指新的和改进的，价格便宜且易于访问的，S需要桌子和绿色，但无功而一般适用哎呀催化剂与高效，可靠地运行在具有一般适用的反应方案低催化剂载量高的官能团耐受性。 二氯二钯（氨基膦）复合物近期推出的那样容易获得，价格便宜，空气中稳定，但高活性CC交叉偶联催化剂具有优良的官能团耐受30-34，其中二氯{双[1,1&#39;，1&#39; &#39; - （phosphinetriyl）tripiperidine]}钯[（P（NC 5 H 10）3）2的Pd（Cl）的2]（1）被证明是，有效地工作在100℃的高效，可靠和灵活的Heck催化剂35 1定量地仅在几分钟之内制备治疗[加入Pd（Cl）的2（COD）]（COD =环辛-1,5 -二烯）与1,1&#39;，1&#39;&#39;的THF悬浮液- （phosphinetriyl空气气氛下）tripiperidine在25°C. 1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine，各个配位体体系在一个步骤中通过滴加过量的哌啶向冷却的PCl 3的乙醚溶液来实现。对1,1的制备“在衬底成本，1&#39;&#39; - （phosphinetriyl）tripiperidine 1克钯前体的小于1€（从化学品供应商的目录价格估计），因此，非常便宜。 <img alt="图3" fo:content-width="6in" fo:src="/files/ftp_upload/51444/51444fig3highres.jpg" SRC="/files/ftp_upload/51444/51444fig3.jpg" /> 图3。钯[（P（NC 5 H 10）3）2的Pd（CL）2]（1） -二氯{双[（phosphinetriyl）tripiperidine 1,1&#39;，1&#39;]}的合成 <a HREF="https://www.jove.com/files/ftp_upload/51444/51444fig3highres.jpg" TARGET="_blank">点击这里查看大图。</a> 此外，尽管在Si投影机的简易和廉价的1合成和其优良的催化性能，添加盐酸水溶液（工作机条件下），导致快速和完整的催化剂降解，伴随着形成膦，哌啶盐和不溶性含钯分解产品，这是很容易从偶联产物分离。这是一个常常被忽视，但很重要的问题需要考虑（但从生态和经济分），是特别重要的药学相关化合物的制备。

<table border="0" cellpadding="0" cellspacing="0" width="722">
	<tbody>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Phosphorous&#160; trichloride</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">157791</td>
			<td style="width:232px;">ReagentPlus, 99%</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Piperidine</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">104094</td>
			<td style="width:232px;">ReagentPlus, 99%</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Dichloro(1,5-cyclooctadiene)palladium(II)</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">275891</td>
			<td style="width:232px;">99%</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Styrene</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">S4972</td>
			<td style="width:232px;">ReagentPlus, contains 4-tert-butylcatechol as stabilizer, &#8805;99%</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">1-Bromo-4-phenoxybenzene</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">B65209</td>
			<td style="width:232px;">99%</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Tetrabutylammonium bromide</td>
			<td style="width:129px;">Acros Organics</td>
			<td style="width:145px;">185680025</td>
			<td style="width:232px;">99+%</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Potassium carbonate</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">347825</td>
			<td style="width:232px;">Reagent grade, &#8805;98%, powder, -325 mesh</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Silica gel</td>
			<td style="width:129px;">Merck</td>
			<td style="width:145px;">107734</td>
			<td style="width:232px;">Silica gel 60 (0.063-0.2mm), for column chromatoraphy</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Diethyl ether</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">673811</td>
			<td style="width:232px;">Anhydrous, ACS reagent, &#8805;99.0%, contains BHT as inhibitor</td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:216px;">Tetrahydrofuran (THF)</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">186562</td>
			<td style="width:232px;">anhydrous, contains 250 ppm BHT as inhibitor, &#8805;99.9%</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">Pentane</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">158941</td>
			<td style="width:232px;">reagent grade, 98%</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:216px;">N-methyl-2-pyrrolidone (NMP)</td>
			<td style="width:129px;">Sigma-Aldrich</td>
			<td style="width:145px;">M79603</td>
			<td style="width:232px;">ReagentPlus, 99%</td>
		</tr>
	</tbody>
</table>

mizoroki-heck cross-coupling reactions catalyzed by dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium under mild reaction conditions

钯二氯-双（氨基膦）配合物的[（p {（NC 5 H 10）3 - N（C 6 H 11）n}的 ）2的Pd（CL）2]通式（其中n = 0-2 ），属于容易访问的，很便宜，而且空气中稳定的一个新的家庭，但非常活跃，普遍适用的CC交叉偶联催化剂具有优良的官能团耐受性。二氯{双[1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine]}钯[（P（NC 5 H 10）3）2的Pd（CL）2]（1），最稳定的这一系列复杂的内朝质子; 例如在水的形式，允许缓和纳米颗粒的形成，因此，被证明是在100℃下该系列中最活跃的Heck催化剂，并且是一种非常罕见的下温和，有效地建立了有效和通用的催化剂体系的例子反应条件进行。快速，完整的c工作式的条件下atalyst降解成膦酸盐，哌啶鎓盐和其他含钯的分解产物保证易于分离，从催化剂和配体的偶联产物。轻便，便宜，快速合成1,1&#39;，1“ - （phosphinetriyl）tripiperidine和1分别使用简单方便，以及在100°Heck反应其优良的催化性能C MAKE 1到一最有吸引力和最环保哎呀催化剂可用。 我们在此提供的配体和催化剂的合成，以及该反应协议为在10毫摩尔规模进行，在100℃，并表明，该催化剂适合于在有机合成中使用的Heck反应的可视化的协议。

<html>上述反应方案成功地应用于与苯乙烯（a）中，1 -乙烯基-3 -硝基苯（b）中 ，1 -氯-3 -乙烯基苯（c）中，1 -乙烯基-4 -甲氧基苯（d）和4 -乙烯基吡啶（五）以及N，N-二甲基丙烯酰胺（f）中，4 -丙烯酰基吗啉（g）和丙烯酸丁酯（ 小时）作为偶联。 表1示出一个选择最近准备交叉偶联产物，并给出关于一个印象此协议的范围35的耦合产物漂亮地形成（ 图4），并且通常在合理范围内的反应时间高收率获得。 E-异构体的芳基化的烯烃常常只形成。 1444fig4highres.jpg“SRC =”/ files/ftp_upload/51444/51444fig4.jpg“/&gt; 图4。在〜10％（摩尔）四丁基溴化铵和0.05％（摩尔）催化剂的存在下记录由乙基4 -溴苯甲酸酯和苯乙烯的Heck反应的反应混合物在100℃下在DMF中，示出了随时间变化的产物形成的气体色谱图。注时相比，在表1中给出的数据，反应时间稍微延长。这是由于周期性采样。 <a href="https://www.jove.com/files/ftp_upload/51444/51444fig4highres.jpg" target="_blank">点击这里查看大图。</a> 因此， 图1是一种廉价，易访问和绿色的，稳定的，因此，方便，反应性高的Heck催化剂具有高的官能团耐受性，从 ​​而有效地和可靠地在低催化剂载量（0.05摩尔％）的工作，有一个简单的适应性和鲁棒反应协议。 。表1的Heck由芳基溴化物与不同烯烃之间的反应，由1催化的衍生交叉偶联产物反应条件：1.0毫摩尔的芳基溴，1.5毫摩尔烯烃，2.0毫摩尔K 2 CO 3 2.5毫升NMP中，四丁基溴化铵（10摩尔％），催化剂（0.05摩尔％）加入溶液（THF）中，使N 2气氛下进行100℃。的转化率和产物比（ 反式/宝石/ CIS）是由GC / MS测定，并根据芳基溴化物。分离产率列于括号内。 [一]二甲基甲酰胺为溶剂。 <a href="https://www.jove.com/files/ftp_upload/51444/51444table1highres.jpg" target="_blank">点击这里查看大图。</a> 钯纳米粒子1的催化活性形式在日ËHeck反应。因此，越来越多的催化剂没有改善，但可以降低催化剂的性能由于形成无活性的钯黑。 溴化四丁基铵是已知的稳定的纳米粒子，是（相对于在140℃下进行的Heck反应）发现是必要的，因为添加剂的可靠转换的基板进入交叉偶联产物用1，在100℃35。 最好的结果是用二甲基甲酰胺时，电子激活或者未活化的芳基溴化物分别施加给A2，A5，A6，A7，A13，A17，A18，B1和H4，例如（ 表1）。 NMP，然而，被认为是选择的溶剂时，电子激活和空间位阻或杂环芳基溴化物分别加上烯烃。例子包括A9的准备，A12，A14，C3，D3，D4，E2，E3，F2，F4，G3，G4，H5和H6（表1）。

Watch this Scientific Journal Video about Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions at JoVE.com

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

二氯{双[1,1&#39;，1&#39;&#39; - （phosphinetriyl）tripiperidine]}钯[（P（NC 5 H 10）3）2的Pd（CL）2]（1）是一种简单方便，价格便宜，而且空气稳定，但是高活性催化剂的Heck用温和的反应条件下，有效地操作，得到偶联产物在非常高的产率优良的官能团耐受性。

Mizoroki-哎呀交叉偶联反应由二氯{双[1,1&#39;，1&#39;&#39;  - （phosphinetriyl）tripiperidine]}钯催化在温和的反应条件

Dichloro-bis(aminophosphine) complexes of palladium with the general formula of [(P{(NC5H10)3-n(C6H11)n})2Pd(Cl)2] (where n = 0-2), belong to a new family ...

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions

Unit 1

Alkene Structure and Reactivity

SCIENTISTS IN ACTION

Particles without a Box: Brush-first Synthesis of Photodegradable PEG Star Polymers under Ambient Conditions

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科研

化学

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Unsymmetrical 1,2-diols are hardly accessible by reductive pinacol coupling processes. A successful execution of such a transformation is bound to a clear ...

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

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The direct functionalization of C-H bonds is an important and long standing goal in organic chemistry. Such transformations can be very powerful in order ...

A Simple Method for the Size Controlled Synthesis of Stable Oligomeric Clusters of Gold Nanoparticles under Ambient Conditions

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Reducing dilute aqueous HAuCl4 with sodium thiocyanate (NaSCN) under alkaline conditions produces 2 to 3 nm diameter nanoparticles. Stable grape-like ...

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一个碗烯官能Hexahelicene的铜（Ⅰ）制备催化的非平面多环芳烃单位炔叠氮化物环加成

The main purpose of this video is to show 6 reaction steps of a convergent synthesis and prepare a complex molecule containing up to three nonplanar ...

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions

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There is a growing research interest in the development of portable systems which can deliver hydrogen on-demand to proton exchange membrane (PEM) ...

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

使用有机锂试剂的一个协议安全的锂化反应

Organolithium reagents are powerful tools in the synthetic chemist&#39;s toolbox. However, the extreme pyrophoric nature of the most reactive reagents ...

Phase Behavior of Charged Vesicles Under Symmetric and Asymmetric Solution Conditions Monitored with Fluorescence Microscopy

用荧光显微镜监测对称和非对称溶液条件下带电泡的相行为

Phase-separated giant unilamellar vesicles (GUVs) exhibiting coexisting liquid-ordered and liquid-disordered domains are a common biophysical tool to ...

Extraction of Lignin with High &#946;-O-4 Content by Mild Ethanol Extraction and Its Effect on the Depolymerization Yield

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Lignin valorization strategies are a key factor for achieving more economically competitive biorefineries based on lignocellulosic biomass. Most of the ...