铜催化交叉偶联反应研究
摘要
本论文包括铜催化的Suzuki-Miyaura交叉偶联反应、Sonogashira交叉偶联反应以及Buchwald-Hartwig N-芳基化偶联反应的研究。
1.对铜催化Suzuki-Miyaura、Sonogashira以及Buchwald-Hartwig等交叉偶联反应按反应类型进行了综述,还详细介绍了铜催化交叉偶联反应中铜盐、配体、溶剂以及其他绿色反应介质的发展情况。
2.发展了廉价而有效的CuI/DABCO(1,4-二氮双环[2,2,2]辛烷)催化系统应用范围,催化烯基卤代烃与芳基硼酸的Suzuki-Miyaura交叉偶联反应。在TBAB促进下,以CuI/DABCO为催化体系,烯基卤代烃与芳基硼酸顺利实现了C-C偶联反应得到了较好的产率和很好的立体选择性,而且该催化体系还发现同样对烯基卤代烃与末端炔烃的Sonogashira交叉偶联反应有效。
3.发展了无配体条件下TBAB(四丁基溴化胺)促进铜催化的芳基卤代烃和芳基硼酸反应的Suzuki-Miyaura交叉偶联反应。在10 mol%的CuI和20 mol%的TBAB催化条件下,各种取代基的碘代芳烃、各种取代基的溴代芳烃以及卤代烯烃和芳基硼酸发生交叉偶联反应得到了较好的产率。
4.发展了无溶剂条件下铜催化含氮杂环化合物N-芳基化C-N偶联反应。在相转移催化剂TBAF中,无需另加溶剂,CuI做催化剂,POPh_3做配体,110℃的条件下,咪唑等含氮唑类化合物和各种取代基的芳香卤代烃实现了N-芳基化C-N偶联反应,产率也较高。
5.发展了无溶剂条件下钯催化活化C-H键的芳基卤代烃与氮甲基咪唑的反应。无溶剂条件下在Pd(OAc)_2,POPh_3和TBAF中,各种卤代烃和氮甲基咪唑顺利反应且获得很好的产率。
This dissertation includes the copper-catalyzed Suzuki-Miyaura cross-coupling reaction, the Sonogashira C-C cross-coupling reaction and the Buchwald-Hartwig N-arylations reaction.
1. Progress in copper-catalyzed cross-coupling reactions, invovling the Suzuki-Miyaura cross-coupling reaction, the Sonogashira cross-coupling reactions and the Buchwald-Hartwig N-arylation reaction, were described. In this chapter, effects of the copper catalyst, ligand, and media on the copper-catalyzed cross-coupling reactions were discussed in detail.
2. CuI combined with DABCO (1,4-diaza-bicyclo[2.2.2]octane) was developed as an inexpensive and efficient catalytic system for the Suzuki-Miyaura cross-coupling of vinyl halides with arylboronic acids. In presence of TBAB, the couplings between vinyl iodides with arylboronic acids catalyzed by catalytic amounts of CuI and DABCO were carried out smoothly in moderate to excellent yields. Moreover, the catalytic system was found to be efficient for the Sonogashira coupling reactions of vinyl halides with terminal alkynes.
3. TBAB (tetra-n-butylammonium bromide) was found to improve the ligand-free copper-catalyzed cross-couplings of aryl halides with arylboronic acids. In the presence of 10 mol% of CuI and 20 mol% of TBAB, a variety of aryl halides underwent the coupling with arylboronic acids smoothly to afford the corresponding products in moderate to good yields.
4. Copper-catalyzed N-arylation of nitrogen-containing heterocycle compounds with aryl halides has been developed. In the presence of CuI, POPh_3 and TBAF, imidazoles and triazoles underwent the N-arylation reaction with a variety of aryl halides smoothly in good yields. It is noteworthy that the reaction was conduct under solvent-free conditions.
5. Palladium-catalyzed C-H bond activation reactions of N-methyl-1H-imidazole with aryl halides have been developed under solvent-free condition. In the presence of Pd(OAc)_2, POPh_3, and TBAF, the reaction of various aryl halides with N-methyl-1H-imidazole was conducted successfully in good yields under solvent-free condition.
1.对铜催化Suzuki-Miyaura、Sonogashira以及Buchwald-Hartwig等交叉偶联反应按反应类型进行了综述,还详细介绍了铜催化交叉偶联反应中铜盐、配体、溶剂以及其他绿色反应介质的发展情况。
2.发展了廉价而有效的CuI/DABCO(1,4-二氮双环[2,2,2]辛烷)催化系统应用范围,催化烯基卤代烃与芳基硼酸的Suzuki-Miyaura交叉偶联反应。在TBAB促进下,以CuI/DABCO为催化体系,烯基卤代烃与芳基硼酸顺利实现了C-C偶联反应得到了较好的产率和很好的立体选择性,而且该催化体系还发现同样对烯基卤代烃与末端炔烃的Sonogashira交叉偶联反应有效。
3.发展了无配体条件下TBAB(四丁基溴化胺)促进铜催化的芳基卤代烃和芳基硼酸反应的Suzuki-Miyaura交叉偶联反应。在10 mol%的CuI和20 mol%的TBAB催化条件下,各种取代基的碘代芳烃、各种取代基的溴代芳烃以及卤代烯烃和芳基硼酸发生交叉偶联反应得到了较好的产率。
4.发展了无溶剂条件下铜催化含氮杂环化合物N-芳基化C-N偶联反应。在相转移催化剂TBAF中,无需另加溶剂,CuI做催化剂,POPh_3做配体,110℃的条件下,咪唑等含氮唑类化合物和各种取代基的芳香卤代烃实现了N-芳基化C-N偶联反应,产率也较高。
5.发展了无溶剂条件下钯催化活化C-H键的芳基卤代烃与氮甲基咪唑的反应。无溶剂条件下在Pd(OAc)_2,POPh_3和TBAF中,各种卤代烃和氮甲基咪唑顺利反应且获得很好的产率。
This dissertation includes the copper-catalyzed Suzuki-Miyaura cross-coupling reaction, the Sonogashira C-C cross-coupling reaction and the Buchwald-Hartwig N-arylations reaction.
1. Progress in copper-catalyzed cross-coupling reactions, invovling the Suzuki-Miyaura cross-coupling reaction, the Sonogashira cross-coupling reactions and the Buchwald-Hartwig N-arylation reaction, were described. In this chapter, effects of the copper catalyst, ligand, and media on the copper-catalyzed cross-coupling reactions were discussed in detail.
2. CuI combined with DABCO (1,4-diaza-bicyclo[2.2.2]octane) was developed as an inexpensive and efficient catalytic system for the Suzuki-Miyaura cross-coupling of vinyl halides with arylboronic acids. In presence of TBAB, the couplings between vinyl iodides with arylboronic acids catalyzed by catalytic amounts of CuI and DABCO were carried out smoothly in moderate to excellent yields. Moreover, the catalytic system was found to be efficient for the Sonogashira coupling reactions of vinyl halides with terminal alkynes.
3. TBAB (tetra-n-butylammonium bromide) was found to improve the ligand-free copper-catalyzed cross-couplings of aryl halides with arylboronic acids. In the presence of 10 mol% of CuI and 20 mol% of TBAB, a variety of aryl halides underwent the coupling with arylboronic acids smoothly to afford the corresponding products in moderate to good yields.
4. Copper-catalyzed N-arylation of nitrogen-containing heterocycle compounds with aryl halides has been developed. In the presence of CuI, POPh_3 and TBAF, imidazoles and triazoles underwent the N-arylation reaction with a variety of aryl halides smoothly in good yields. It is noteworthy that the reaction was conduct under solvent-free conditions.
5. Palladium-catalyzed C-H bond activation reactions of N-methyl-1H-imidazole with aryl halides have been developed under solvent-free condition. In the presence of Pd(OAc)_2, POPh_3, and TBAF, the reaction of various aryl halides with N-methyl-1H-imidazole was conducted successfully in good yields under solvent-free condition.
引文
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(c)Percee,V;Golding,G,M.;Smidrkal,J.;Weichold,O.NiCl_2(dppe)-Catalyzed Cross-Coupling of Aryl Mesylates,Arenesulfonates,and Halides with Arylboronic Acids[J].J.Org.Chem.2004,69,3447.
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[2].For specil reviews on copper-catalyzed cross-couplings,see(a)Peter Siemsen,Robert C.Livingston,Francois Diederich.Acetylenic Coupling:A Powerful Tool in Molecular Construction[J].Angew.Chem.Int.Ed.2000,39,2632.
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[3](a)Trahanovsky,W,S.Oxidation in Organic Chemisty[M].Academic Press;New York and London,1973;5-B.
(b)Bringmann,G;Gunther,C;Ochse,M;Schupp O;and Tasler,S.In Progress in the Chemistry of Organic Natural Products[M].Spring:New York,2001,82,1-293.
[4]For representative papers on the nickel-catalyzed Suzuki-Miyaura CrossCouplingreaction,see(a)Saito,S;Ohtani,S;Miyaura,N.Synthesis of Biaryls via a Nickel(0)-Catalyzed Cross-Coupling Reaction of Chloroarenes with Arylboronic Acids[J].J.Org.Chem,1997,62,8024.
(b)Zim,D;Lando,V.R;Dupond,J.;Monteiro,A.L.NiCl_2(PCy_3)_2:A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids[J].Org.Lett.2001,3,3049.
(c)Percee,V;Golding,G,M.;Smidrkal,J.;Weichold,O.NiCl_2(dppe)-Catalyzed Cross-Coupling of Aryl Mesylates,Arenesulfonates,and Halides with Arylboronic Acids[J].J.Org.Chem.2004,69,3447.
[5]. For representative papers on the nickel-catalyzed Sonogashira cross-coupling,see (a) Irina P Beletskaya, Gennadij V Latyshev, Alexey V Tsvetkov and Nikolai V Lukashev. The nickel-catalyzed Sonogashira-Hagihara reaction [J]. Tetrahedron Lett. 2003,44, 5011- 5013. (b) Beletskaya, I. P; Latyshev, G. V; Tsvetkov, A.V; Lukashev, N. V. The nickel-catalyzed Sonogashira-Hagihara reaction [J]. Tetrahedron Lett. 2003,44, 5011.
[6]. Rothenberg, G.; Thathagar, M. B.; Beckers, J. Copper-Catalyzed Suzuki Cross-Coupling Using Mixed Nanocluster Catalysts [J]. J. Am. Chem. Soc. 2002, 124,11858.
[7]. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines [J]. Tetrahedron Lett. 1975,16, 4467
[8]. For papers on the Sonogashira cross-coupling reaction catalyzed by a catalytic amount of copper ,see (a) Kazumi Okuro, Makoto Furuune, Masahiro Enna, Masahiro Miura, and Masakatau Nomura. Synthesis of Aryl- and Vinylacetylene Derivatives by Copper-Catalyzed Reaction of Aryl and Vinyl Iodides with Terminal Alkynes [J]. J.Org.Chem. 1993, 58,4716. (b) Rattan K. Gujadhur, Craig G. Bates, and D. Venkataraman. Formation of Aryl-Nitrogen, Aryl-Oxygen, and Aryl-Carbon Bonds Using Well-Defined Copper(I)-Based Catalysts [J]. Org. Lett. 2001, 3,4315.
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