CN109134333A - 一种硒硫醚化合物的制备方法 - Google Patents

一种硒硫醚化合物的制备方法 Download PDF

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CN109134333A
CN109134333A CN201810964631.3A CN201810964631A CN109134333A CN 109134333 A CN109134333 A CN 109134333A CN 201810964631 A CN201810964631 A CN 201810964631A CN 109134333 A CN109134333 A CN 109134333A
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赵晓丹
刘想
安锐
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Sun Yat Sen University
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Abstract

本发明公开了一种硒硫醚化合物的制备方法，本发明通过在催化量的三氟甲磺酸和偶氮二甲酸二乙酯的作用下，可以有效的氧化断裂S‑S(Se‑Se)键，产生硫正离子或者硒正离子，该正离子接受不同亲核试剂的进攻可以得到多种类型的硒硫醚化合物。当采用烯酸、烯醇或者烯胺为底物时，通过该方法分别能高效的得到环化的烷基硒硫醚化合物。当采用芳基硼酸或芳环为底物时，通过该方法能合成不对称的芳基硒硫醚化合物。本发明简单易于操作，不含金属参与，快捷方便条件温和，反应底物适用范围广，区域选择性好，收率高，可高效的合成多种类型的硒硫醚化合物。

Description

一种硒硫醚化合物的制备方法
技术领域：
本发明涉及一种硒硫醚化合物的制备方法。
背景技术：
有机硒硫化合物普遍存在于天然产物、药物和生物活性分子中((a)Dunbar,K.L.；Scharf,D.H.；Litomska,A.；Hertweck,C.Chem.Rev.2017,117,5521.(b)Chauhan,P.；Mahajan,S.；Enders,D.Chem.Rev.2014,114,8807.(c)Reich,H.J.；Hondal,R.J.；ACSChem.Biol.2016,11,821.)。通过直接C-S(C-Se)键的形成来构建有机硒硫化合物是一种重要的途径((a)Liu,H.；Jiang,X.Chem.Asian J.2013,8,2546.(b)Shen,C.；Zhang,P.；Sun,Q.；Bai,S.；Hor,T.S.A.；Liu,X.Chem.Soc.Rev.2015,44,291.(c)Yu,J.-S.；Huang,H.-M.；Ding,P.-G.；Hu,X.-S.；Zhou,F.；Zhou,J.ACS Catal.2016,6,5319.)。过去几十年来，由硫正离子(硒正离子)的亲电官能化来形成C-S(C-Se)键受到研究者的重视。通常有三种途径产生硫正离子(硒正离子)：(1)直接活化亲电性硫(硒)正离子试剂((a)Denmark,S.E.；Hartmann,E.；Kornfilt,D.J.P.；Wang,H.Nat.Chem.2014,6,1056.(b)Zhu,D.；Gu,Y.；Lu,L.；Shen,Q.J.Am.Chem.Soc.2015,137,10547.(c)Liu,X.；An,R.；Zhang,X.；Luo,J.；Zhao,X.Angew.Chem.Int.Ed.2016,55,5846.)；(2)氧化低价硒硫化合物((a)Vieira,A.A.；Azeredo,J.B.；Godoi,M.；Santi,C.；Junior,E.N.da S.；Braga,A.L.J.Org.Chem.2015,80,2120.(b)Zheng,Y.；He,Y.；Rong,G.；Zhang,X.；Weng,Y.；Dong,K.；Xu,X.；Mao,J.Org.Lett.2015,17,5444.(c)Huang,D.；Chen,J.；Dan,W.；Ding,J.；Liu,M.；Wu,H.Adv.Synth.Catal.2012,354,2123.)；(3)还原高价硒硫化合物((a)F.-L.；Yang,S.-K.Tian,Angew.Chem.Int.Ed.2013,52,4929.(b)Wu,Z.；Li,Y.-C.；Ding,W.-Z.；Zhu,T.；Liu,S.-Z.；Ren,X.；Zou,L.-H.Asian J.Org.Chem.2016,5,625.(c)Fernández-Salas,J.A.；Pulis,A.P.；Procter,D.J.Chem.Commun.2016,52,12364.)。在众多方法当中，氧化二硫醚(二硒醚)产生硫正离子(硒正离子)被认为是一种理想的途径。一方面，二硫醚(二硒醚)在空气中稳定且易于保存((a)Wang,M.；Ren,K.；Wang,L.Adv.Synth.Catal.2009,351,1586.(b)Ren,K.；Wang,M.；Wang,L.Org.Biomol.Chem.2009,7,4858.)。另一方面，可以避免使用恶臭味的硫、硒醇和预制备高价硒硫醚化合物(Roy,S.；Chatterjee,T.；Islam,Sk.M.Tetrahedron Lett.2015,56,779.)。通常，氧化裂解S-S(Se-Se)键需要强氧化剂、毒性溶剂、高温和长的反应时间。这些苛刻的条件使得反应类型和官能团兼容性受到限制。所以，迫切需要发展通用的氧化体系来断裂S-S(Se-Se)键，快速构建多样的有机硒硫醚化合物。
偶氮类化合物是一类重要的有机试剂，广泛应用于染料((a)Bafana,A.；Devi,S.S.；Chakrabarti,T.Environ.Rev.2011,19,350.(b)Chung,K.-T.J.Environ.Sci.HealthC,2016,34,233.)、自由基引发剂((a)Inui,T.；Yamanishi,K.；Sato,E.；Matsumoto,A.Macromolecules 2013,46,8111.(b)Zenati,A.；Han,Y.-K.Macromolecules 2018,51,101.)和脱氢试剂((a)But,T.Y.S.；Toy,P.H.Chem.Asian J.2007,2,1340.(b)Swamy,K.C.K.；Kumar,N.N.B.；Balaraman,E.；Kumar,K.V.P.P.Chem.Rev.2009,109,2551.(c)Fletcher,S.Org.Chem.Front.2015,2,739.)。特别的，带有强吸电子基团的偶氮类化合物因其N-N键的缺电性被认为是强的电子受体((a)Yoneda,F.；Suzuki,K.；Nitta,Y.J.Am.Chem.Soc.1966,88,2328.(b)Axen,R.；Chaykovsky,M.；Witkop,B.J.Org.Chem.1967,32,4117.(c)Jung,D.；Kim,M.H.；Kim,J.Org.Lett.2016,18,6300.)。最近，这些亲电性的偶氮物种因其好的官能团容忍性、温和的反应条件和操作简易，在一些氧化反应中扮演着氧化剂的角色。比如醇、胺脱氢转化为羰基化合物和亚胺，氧化硫醇为二硫醚和氧化硫化物为亚砜类化合物等等((a)Koichi,N.；Anri,M.；Kazuhiko,S.；Teruaki,M.B.Chem.Soc.Jpn.1977,50,2773.(b)Wang,G.；Piva de Silva,G.；Wiebe,N.E.；Fehra,G.M.；Davis,R.L.RSC Adv.2017,7,48848.)。尽管已经有这些研究工作，但是通过偶氮类化合物氧化断裂二硫(硒)醚中的S-S(Se-Se)键还没有人报道过。
因此，我们发展了一种酸催化DEAD促进的氧化断裂S-S(Se-Se)键的新方法，具体为在催化量三氟甲磺酸和偶氮二甲酸二乙酯的作用下实现S-S(Se-Se)键的断裂及其在制备多种类型的硒硫醚化合物中的应用。
发明内容：
本发明的目的是克服现有技术的不足，提供一种酸催化DEAD促进的氧化断裂S-S(Se-Se)键的制备硒硫醚化合物的方法。
为了实现上述目的，本发明采用如下技术方案：
本发明公开了一种酸催化下DEAD促进的氧化断裂S-S(Se-Se)键的新方法，本发明通过在催化量的三氟甲磺酸和偶氮二甲酸二乙酯的作用下，可以有效的氧化断裂S-S(Se-Se)键，产生硫正离子或者硒正离子，该正离子接受不同亲核试剂的进攻可以得到多种类型的硒硫醚化合物。当采用烯酸、烯醇或者烯胺为底物时，通过该方法分别能高效的得到环化的烷基硒硫醚化合物。当采用芳基硼酸或芳环为底物时，通过该方法能合成不对称的芳基硒硫醚化合物。
一种硒硫醚化合物的制备方法，其表达式为：
式1化合物与R4EER4在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；基团R1、R2、R3、R4为芳基或者烷基；E为S或者Se原子；n为1或2；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷。
一种硒硫醚化合物的制备方法，其表达式为：
式3化合物与二苯基二硫醚或二芳基二硒醚或二芳基二硫醚在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团R1、R2为芳基或者烷基。
一种硒硫醚化合物的制备方法，其表达式为：
式5化合物与二苯基二硫醚或二芳基二硒醚或二芳基二硫醚在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团R1、R2为芳基或者烷基。
一种硒硫醚化合物的制备方法，其表达式为：
式7化合物与R4EER4在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟化硼—乙醚络合物、三氟甲磺酸、三氟甲磺酸三甲基硅酯或双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团Ar为芳基；基团R4为芳基或者烷基；E为S或者Se原子。
与现有技术相比，本发明具有如下有益效果：本发明的硒硫醚化合物制备方法，简单易于操作，不含金属参与，快捷方便条件温和，反应底物适用范围广，区域选择性好，收率高，可高效的合成多种类型的硒硫醚化合物，在天然产物和药物制备方面具有广阔的应用前景。本发明所使用的试剂廉价易得，避免了使用硫酚等有恶臭味的试剂，改善了反应的环境友好性，绿色环保。
具体实施方式：
以下结合实施例对本发明作进一步说明。
实施例1：
将25.2mg(0.15mmol)4-苯基-3-丁烯酸、19.8mg(0.09mmol)二苯基二硫醚置于20ml带有搅拌子的反应瓶中，于室温加入3mL二氯甲烷后，再分别加入14.4uL(0.09mmol)偶氮二甲酸二乙酯和0.7uL(0.0075mmol)TfOH，在室温搅拌12小时，旋干后快速柱层析得到目标产物，99％产率。
1H NMR(400MHz,CDCl3)δ7.56–6.98(m,10H),5.31(d,J＝5.8Hz,10H),3.80(dd,J＝13.9,7.0Hz,1H),2.99(dd,J＝18.0,8.2Hz,1H),2.62(dd,J＝18.0,7.0Hz,1H).
13C NMR(101MHz,CDCl3)δ174.25,137.40,133.37,133.30,131.80,129.44,128.87,128.83,128.57,125.50,85.17,76.84,49.91,35.45.
HR-ESI-MS m/z calcd.for C16H15O2S[M+H]+:271.0787；found:271.0786。
实施例2：
将22.2mg(0.15mmol)如下所示烯醇、19.8mg(0.09mmol)二苯基二硫醚置于20ml带有搅拌子的反应瓶中，于室温加入3mL二氯甲烷后，再分别加入14.4uL(0.09mmol)偶氮二甲酸二乙酯和1.3uL(0.015mmol)TfOH，在室温搅拌12小时，旋干后快速柱层析得到目标产物，88％产率。
1H NMR(400MHz,CDCl3)δ7.36–7.28(m,6H),7.22(dt,J＝14.5,6.4Hz,4H),4.77(d,J＝5.7Hz,1H),4.25–4.16(m,1H),4.08(q,J＝7.8Hz,1H),3.61(dd,J＝12.7,5.7Hz,1H),2.45(dq,J＝15.4,7.7Hz,1H),2.07(td,J＝12.0,5.0Hz,1H).
13C NMR(101MHz,CDCl3)δ141.41,134.87,131.61,129.08,128.49,127.83,127.13,125.91,85.73,68.00,53.71,33.9.
HR-ESI-MS m/z calcd.for C16H17OS[M+H]+:257.0994；found:257.0994。
实施例3：
将45.2mg(0.15mmol)如下所示烯胺、19.8mg(0.09mmol)二苯基二硫醚置于20ml带有搅拌子的反应瓶中，于室温加入3mL二氯甲烷后，再分别加入14.4uL(0.09mmol)偶氮二甲酸二乙酯和0.7uL(0.0075mmol)TfOH，在室温搅拌12小时，旋干后快速柱层析得到目标产物，95％产率。
1H NMR(400MHz,CDCl3)δ7.70(d,J＝7.8Hz,2H),7.41–7.01(m,12H),4.64(s,1H),3.78(t,J＝7.9Hz,1H),3.60(dd,J＝17.9,7.8Hz,2H),2.45(s,3H),2.36–2.21(m,1H),1.83–1.70(m,1H).
13C NMR(101MHz,CDCl3)δ143.51,141.68,134.56,133.58,132.30,129.58,129.13,128.51,127.86,127.71,127.52,126.04,68.75,55.55,47.93,29.26,21.65.
HR-ESI-MS m/z calcd.for C23H24O2NS2[M+H]+:410.1243；found:410.1239。
实施例4：
将25.2mg(0.15mmol)苯硼酸、28.2mg(0.09mmol)二苯基二硒醚置于20ml带有搅拌子的反应瓶中，于室温加入3mL二氯甲烷后，再分别加入14.4uL(0.09mmol)偶氮二甲酸二乙酯和3.7uL(0.03mmol)三氟化硼—乙醚络合物，在室温搅拌12小时，旋干后快速柱层析得到目标产物，94％产率。
1H NMR(400MHz,CDCl3)δ7.51–7.42(m,4H),7.32–7.21(m,6H).
13C NMR(101MHz,CDCl3)δ133.11,131.26,129.46,127.46。

Claims (4)

1.一种硒硫醚化合物的制备方法，其特征在于：其表达式为：
式1化合物与R4EER4在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；基团R1、R2、R3、R4为芳基或者烷基；E为S或者Se原子；n为1或2；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷。
2.一种硒硫醚化合物的制备方法，其特征在于：其表达式为：
式3化合物与二苯基二硫醚或二芳基二硒醚或二芳基二硫醚在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团R1、R2为芳基或者烷基。
3.一种硒硫醚化合物的制备方法，其特征在于：其表达式为：
式5化合物与二苯基二硫醚或二芳基二硒醚或二芳基二硫醚在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟甲磺酸、三氟甲磺酸三甲基硅酯、三氟化硼—乙醚络合物或者双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团R1、R2为芳基或者烷基。
4.一种硒硫醚化合物的制备方法，其特征在于：其表达式为：
式7化合物与R4EER4在溶剂中进行反应，催化剂为强酸和偶氮类化合物的混合物，所述强酸为三氟化硼—乙醚络合物、三氟甲磺酸、三氟甲磺酸三甲基硅酯或双(三氟甲烷磺酰基)亚胺；所述偶氮类化合物为偶氮二甲酸二乙酯、偶氮二甲酸二异丙酯或偶氮二甲酸二苄酯；所述溶剂为二氯甲烷、三氯甲烷或1,2-二氯乙烷；基团Ar为芳基；基团R4为芳基或者烷基；E为S或者Se原子。
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