CN106008265A - 一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法 - Google Patents

一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法 Download PDF

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CN106008265A
CN106008265A CN201610344744.4A CN201610344744A CN106008265A CN 106008265 A CN106008265 A CN 106008265A CN 201610344744 A CN201610344744 A CN 201610344744A CN 106008265 A CN106008265 A CN 106008265A
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quaternary ammonium
ammonium salt
benzyl quaternary
suzuki coupling
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王涛
杨书武
赵军锋
余维洁
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Jiangxi Normal University
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract

一种钯催化苄基季铵盐C‑N键断裂Suzuki偶联的方法，该类化合物的结构经1H NMR、13C NMR、HRMS等方法表征并得以确认。本发明使用一系列苄基季铵盐类化合物与有机硼试剂在PdCl2催化下，PPh3为配体，Na2CO3为碱，在EtOH中100℃氮气条件下生成相应的二芳基甲烷类化合物；该反应可高效得到目标产物（部分反应可以当量转化）。本发明方法条件温和，底物适用范围广，收率高；相比于镍催化季铵盐C‑N键断裂的Suzuki偶联反应，操作简便；在该发明方法中，使用乙醇作为溶剂，相比于之前的方法环境友好，绿色环保，还能抑制硼酸的自身偶联发生；产品纯度高，便于分离，可适用于大规模的制备，具有广泛的应用前景。

Description

一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法
技术领域
本发明属于有机化学技术领域，具体涉及钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法。
背景技术
在有机合成化学中，过渡金属催化的Suzuki交叉偶联反应已经成为一种非常重要的构建碳-碳键的反应。有机硼试剂本身具有低毒、对空气和湿度稳定、良好的底物适用性、官能团容忍性，且易合成；因此，Suzuki偶联反应在有机合成中被广泛的应用。近年来，通过C-N键断裂的Suzuki偶联反应备受关注；季铵盐作为一种简单易得的含氮化合物，备受有机化学家们的青睐。然而，目前报道的季铵盐C-N键断裂的Suzuki偶联的反应只能在镍催化的条件下进行。2003年，MacMillan课题组1首次报道了季铵盐与芳基硼酸的Suzuki交叉偶联反应；该反应以三甲基芳基三氟甲磺酸铵和芳基硼酸为原料，镍催化条件下进行交叉偶联；能得到中等到优秀的产率，且官能团容忍性好。但是，MacMillan在文中指出，该反应在钯催化条件下是不能进行的。2013年，同样是在镍催化条件下，Watson课题组2报道了三甲基苄基三氟甲磺酸铵与芳基硼酸的Suzuki交叉偶联反应；
基于以上文献报道，镍催化季铵盐C-N键断裂的Suzuki偶联反应的方法已成熟；然而，通过钯催化季铵盐C-N键断裂的Suzuki偶联反应的方法还存在着巨大的挑战。鉴于镍催化剂对空气和湿度敏感；相比之下，钯催化剂稳定、便于操作；因此，寻求一种钯催化季铵盐C-N键断裂的Suzuki偶联反应的方法尤为重要。
参考文献
1.Blakey,S.B.；MacMillan,D.W.,The first Suzuki cross-couplings of aryltrimethylammonium salts.Journal of the American Chemical Society 2003,125,6046-7.
2.Maity,P.；Shacklady-McAtee,D.M.；Yap,G.P.；Sirianni,E.R.；Watson,M.P.,Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids:stereospecific formation of diarylethanes via C-N bond activation.Journal of the American Chemical Society 2013,135,280-5.
发明内容
本发明的目的在于提供一种新的钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法；相比于镍催化，钯催化操作更简便、更利于放大实验的完成、应用更广泛。
本发明是苄基季铵盐类化合物1与有机硼试剂2以PdCl2为催化剂，PPh3为配体，Na2CO3为碱，在EtOH溶剂中N2条件下反应24h合成相应的二苯甲烷类化合物；首先，苄基季铵盐类化合物1在PdCl2催化下形成C-Pd物种B,有机硼试剂在碱的条件下与物种B进行转金属化后还原消除直接得到目标产物3。其可能机理如下：
所述钯催化苄基季铵盐C-N键断裂Suzuki偶联的反应式为：
所述钯催化苄基季铵盐C-N键断裂Suzuki偶联的具体步骤为：
(1)将0.2mmol苄基季铵盐,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),有机硼试剂(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mLEtOH溶剂。
(2)反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗,将滤液集中，通过柱层析得到二苯甲烷类化合物。
本发明最佳反应条件：
(1)反应体系所用的催化剂为3mol％PdCl2；
(2)反应体系所用的配体为10mol％PPh3；
(3)反应体系所用的碱为2equiv Na2CO3；
(4)反应温度为100℃；反应时间为24h。
本发明的有益效果:本方法条件温和，底物适用范围广，收率高，便于分离提纯；较之于镍催化季铵盐C-N键断裂的Suzuki偶联反应，本发明操作简便，溶剂为乙醇，对环境友好、绿色环保；可适用于大规模的制备，具有非常好的应用前景。
具体实施方式
实例1
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，无色液体，收率98％。
1H NMR(400MHz,CDCl3)δ7.46(d,J＝8.2Hz,2H),7.29–7.10(m,5H),7.07(d,J＝7.0Hz,2H),3.94(s,2H).13C NMR(100MHz,CDCl3)δ146.3,138.9,131.8,129.2,128.5,128.3,126.2,118.5,109.6,41.5.HRMS(ESI+)calculated for C14H11N[M+H]+:194.0970；found:194.0969.
实例2
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-甲基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂， 100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，黄色液体，收率99％。
1H NMR(400MHz,CDCl3)δ7.46(d,J＝8.1Hz,2H),7.18(d,J＝8.1Hz,2H),7.03(d,J＝7.8Hz,2H),6.96(d,J＝7.9Hz,2H),3.89(s,2H),2.23(s,3H).13C NMR(100MHz,CDCl3)δ147.1,136.3,136.3,132.3,129.6,129.5,128.9,119.1,110.0,41.6,21.1.HRMS(ESI+)calculated for C15H13N[M+H]+:208.1126；found:208.1121.
实例3
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-氟苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，浅黄色液体，收率95％。
1H NMR(400MHz,CDCl3)δ7.57(d,J＝7.6Hz,2H),7.26(d,J＝7.8Hz,2H),7.15–7.07(m,2H),6.99(t,J＝8.3Hz,2H),4.00(s,2H).13C NMR(100MHz,CDCl3)δ161.7(d,JC-F＝244.5Hz),146.5,135.0(d,JC-F＝3.3Hz),132.4,130.4(d,JC-F＝7.9Hz),129.6,118.9,115.6(d,JC-F＝21.4Hz),110.2,41.1.HRMS(ESI+)calculated for C14H10FN[M+H]+:212.0876；found:212.0880.
实例4
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol), PPh3(5.3mg,0.02mmol),4-氯苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，白色固体，收率89％。
1H NMR(400MHz,CDCl3)δ7.57(d,J＝7.2Hz,2H),7.22-7.29(m,4H),7.08(d,J＝7.4Hz,2H),4.00(s,2H).13C NMR(100MHz,CDCl3)δ146.1,137.8,132.6,132.4,130.3,129.6,128.9,118.9,110.3,41.3.HRMS(ESI+)calculated for C14H10ClN[M+H]+:228.0580；found:228.0575.
实例5
将0.2mmol 4-三氟甲基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-氰基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，黄色固体，收率83％。
1H NMR(400MHz,CDCl3)δ7.58(t,J＝8.3Hz,4H),7.28(d,J＝7.9Hz,4H),4.09(s,2H).13C NMR(100MHz,CDCl3)δ145.5,143.4,132.5,129.7,129.3,128.9,125.7(q,JC-F＝3.78Hz),124.1(q,JC-F＝272.4Hz),118.8,110.5,41.7.HRMS(ESI+)calculated for C15H10F3N[M+H]+:262.0844；found:262.0846.
实例6
将0.2mmol2-萘三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol), PPh3(5.3mg,0.02mmol),4-氰基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，白色固体，收率86％。
1H NMR(400MHz,CDCl3)δ7.83–7.74(m,3H),7.60(s,1H),7.56(d,J＝8.1Hz,2H),7.50–7.40(m,2H),7.31(d,J＝8.1Hz,2H),7.25(d,J＝6.9Hz,1H),4.18(s,2H).13C NMR(100MHz,CDCl3)δ146.6,136.8,133.6,132.4,132.3,129.8,128.5,127.7,127.6,127.4,127.3,126.3,125.8,119.0,110.2,42.1.HRMS(ESI+)calculated for C18H13N[M+Na]+266.0946；found:266.0944.
实例7
将0.2mmol4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),1-萘基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，白色固体，收率95％。
1H NMR(400MHz,CDCl3)δ7.83(ddd,J＝14.5,11.2,5.1Hz,3H),7.51(d,J＝8.3Hz,2H),7.49–7.40(m,3H),7.26(dd,J＝13.5,7.6Hz,3H),4.46(s,2H).13C NMR(100MHz,CDCl3)δ146.4,134.9,134.1,132.3,131.9,129.4,128.9,127.9,127.7,126.4,125.9,125.6,123.9,119.0,110.1,39.2.HRMS(ESI+)calculated for C18H13N[M+H]+:244.1126；found:244.1122.
实例8
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-联苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，白色固体，收率92％。
1H NMR(400MHz,CDCl3)δ7.60–7.50(m,6H),7.42(t,J＝7.4Hz,2H),7.32(dd,J＝12.1,7.7Hz,3H),7.22(d,J＝7.7Hz,2H),4.06(s,2H).13C NMR(100MHz,CDCl3)δ146.7,140.7,139.7,138.4,132.4,129.7,129.4,128.8,127.5,127.3,127.0,119.0,110.2,41.6.HRMS(ESI+)calculated for C20H15N[M+H]+:270.1283；found:270.1277.
实例9
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-甲酰基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，黄色固体，收率89％。
1H NMR(400MHz,CDCl3)δ9.99(s,1H),7.83(d,J＝7.8Hz,2H),7.59(d,J＝8.0Hz,2H),7.34(d,J＝7.8Hz,2H),7.29(d,J＝7.9Hz,2H),4.12(s,2H).13C NMR (100MHz,CDCl3)δ191.8,146.4,145.3,135.1,132.5,130.2,129.7,129.6,118.8,110.6,42.0.HRMS(ESI+)calculated for C15H11NO[M+H]+:222.0919；found:222.0920.
实例10
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),3-吡啶硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，黄色液体，收率89％。
1H NMR(400MHz,CDCl3)δ8.50(s,2H),7.59(d,J＝7.6Hz,2H),7.46(d,J＝7.7Hz,1H),7.35–7.20(m,3H),4.05(s,2H).13C NMR(100MHz,CDCl3)δ150.1,148.2,145.3,136.4,134.9,132.5,129.6,123.7,118.7,110.6,39.1.HRMS(ESI+)calculated for C13H10N2[M+H]+:195.0922；found:195.0919.
实例11
将0.2mmol 4-甲酸乙酯三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-氰基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，白色固 体，收率91％。
1H NMR(400MHz,CDCl3)δ7.99(d,J＝8.0Hz,2H),7.58(d,J＝8.0Hz,2H),7.28(d,J＝7.9Hz,2H),7.23(d,J＝7.9Hz,2H),4.37(q,J＝7.1Hz,2H),4.08(s,2H),1.38(t,J＝7.1Hz,3H).13C NMR(100MHz,CDCl3)δ166.3,145.8,144.5,132.4,130.1,129.7,129.0,129.0,118.9,110.4,61.0,41.9,14.4.HRMS(ESI+)calculated for C17H15NO2[M+H]+:266.1181；found:266.1176.
实例12
将0.2mmol 4-氰基三甲基苄基三氟甲磺酸铵,PdCl2(1.1mg,0.006mmol),PPh3(5.3mg,0.02mmol),4-乙烯基苯硼酸(0.4mmol)和Na2CO3(0.4mmol,42.4mg)加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mL EtOH溶剂，100℃搅拌反应24小时；反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗。将滤液集中，通过柱层析得到目标产物，黄色固体，收率92％。
1H NMR(400MHz,CDCl3)δ7.55(d,J＝8.0Hz,2H),7.35(d,J＝7.9Hz,2H),7.26(d,J＝8.0Hz,2H),7.11(d,J＝7.9Hz,2H),6.68(dd,J＝17.6,10.9Hz,1H),5.71(d,J＝17.6Hz,1H),5.22(d,J＝10.9Hz,1H),4.00(s,2H).13C NMR(100MHz,CDCl3)δ146.7,139.0,136.4,136.1,132.3,129.6,129.2,126.6,119.0,113.8,110.1,41.7.HRMS(ESI+)calculated for C16H13N[M+H]+:220.1126；found:220.1121。

Claims (5)

1.一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法，其特征在于：
(1)所述钯催化苄基季铵盐C-N键断裂Suzuki偶联的反应式为：
(2)所述钯催化苄基季铵盐C-N键断裂Suzuki偶联的具体步骤为：
(A)将0.2mmol的苄基季铵盐,1.1mg、0.006mmol的PdCl2,5.3mg、0.02mmol的PPh3,0.4mmol的有机硼试剂和0.4mmol、42.4mg的Na2CO3加入到有磁子的反应管中，随后在氮气氛围中通过注射器加入3mLEtOH溶剂,加温搅拌；
(B)反应结束后，用3mL乙醚稀释反应液，过滤，并用10mL乙醚冲洗,将滤液集中，通过柱层析得到二苯甲烷类化合物。
2.根据权利要求1所述的一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法，其特征在于：所述反应体系所用的催化剂为3mol％PdCl2。
3.根据权利要求1所述的一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法，其特征在于：所述反应体系所用的配体为10mol％PPh3。
4.根据权利要求1所述的一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法，其特征在于：所述反应体系所用的碱为2equiv Na2CO3。
5.根据权利要求1所述的一种钯催化苄基季铵盐C-N键断裂Suzuki偶联的方法，其特征在于：所述反应温度为100℃；反应时间为24h。
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CN112958161A (zh) * 2021-02-22 2021-06-15 江南大学 一种钯催化剂及在催化芳基乙醇类化合物脱氧偶联反应中的应用
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