Rh(Ⅲ)催化C-H活化官能化反应及吲哚杂环合成研究
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摘要
过渡金属催化C-H活化提供了绿色、原子经济的化学合成方法。多种过渡金属(Pd、Ru、Ir等)催化的C-H活化官能化反应得到广泛的研究。近年来,Rh(III)催化C-H活化反应也得到了充分的发展,并为重要活性药物分子合成提供了有效的方法。该论文首先综述了Rh(III)催化C-H活化烯基化、烷基化、氨化等官能化反应以及在杂环合成上的应用。从而得出结论,进一步发展Rh(Ⅲ)催化C-H活化官能化反应及杂环化合物合成的新方法,并实现重要活性药物分子的合成,仍是有机合成化学中一项重要的课题。
1. Rh催化酚酯导向C-H活化氧化Heck反应。我们首次实现酚酯导向的氧化Heck反应。反应可以有效的兼容Br, Cl等基团；多种烯烃底物都可以得到很好的反应。与Pd(Ⅱ)催化的Heck反应相比,反应实现很好的区域选择性控制。反应提供了合成2-烯基取代苯酚衍生物有效方法。
2. Rh催化C-H活化与联烯反应合成共轭烯烃反应。我们实现了Rh催化下C-H活化与联烯化合物反应合成共轭烯烃化合物。反应不仅可以实现烯烃C-H底物的反应,芳基C-H底物也可以得到很好的实现。反应产物可以转化为为其他重要骨架分子。
3.Rh催化C-H活化氰基化反应。首次实现了RRh(Ⅲ)催化下的C-H活化氰基化反应合成芳基腈化合物。反应使用NCTS作为氰基试剂来源,这是一种低毒易得的氰基化试剂。多种导向基都可以实现邻位的C-H活化氰基化反应；反应可以很好的兼容Br、I、酚羟基、环氧等重要的基团；芳香杂环底物也能得到很好的反应效果；反应可以实现复杂分子的C-H氰基化衍生。
4. Rh催化C-H活化合成2-甲基吲哚化合物。我们成功实现了Rh(Ⅲ)催化下,乙酰苯胺衍生物与烯丙醇酯反应得到2-甲基吲哚化合物。反应具有很好的官能团兼容性,Br、I、杂环等重要基团都可以很好的兼容；反应产物可以经过转化得到其他重要结构的化合物；并且我们实现了从简单酰胺原料出发合成两个重要的药物分子。
Transition-metal catalyzed C-H bond activation provides an atom-and step-economical approach for organic synthesis. A variety of transition metals (Pd, Ru, Ir, etc.) catalyzed C-H activation functionalization reaction have been developed. In the past five years, Rh (Ⅲ) catalyzed C-H activation reactions have been fully developed, and provides an effective method for the synthesis of biologically active compounds. This paper first reviews the Rh(III) catalyzed C-H activation functionalization reactions and application in the synthesis of heterocyclic. Notwithstanding these pioneering examples, further development of Rh(III) catalyzed C-H activation reactions reactions is needed in synthetic organic chemistry.
1. Rhodium-Catalyzed C-H Activation/Olefination of Phenol Carbamates. We reported a practical protocol for ortho C-H activation/olefination of phenol carbamates. The reaction tolerates a variety of important functional groups (aryl-Br, aryl-Cl) and many different olefins can be used in this process. This reaction exhibits different reactivity as compared to the Pd-catalyzed processes, this method provide a new approach for the synthesis of ortho-substituted phenols.
2. Rh-catalyzed C-H bond activation with allenes to produce highly unsaturated conjugated olefins. Rh(Ⅲ) catalyzed C-H bond activation with allenes to produce unsaturated conjuncted olefins was reported. The reaction is applicable to both olefin and arene C(Sp2)-H, compatible with varieties of functional groups. The obtained products can be transformed into other important skeletons.
3. Rhodium-catalyzed Directed C-H Cyanation. We report the first example of Rh-catalyzed directed C-H cyanation. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this cyanation process and the reaction tolerates a variety of important functional groups (aryl-Br, aryl-I unprotected phenol, epoxide), A number of heteroaromatic nitriles were successfully synthesized by using this method, the reaction may provide a practical tool for rapid derivatization of bioactive compounds.
4. A practical Rh-catalyzed reaction was developed to achieve2-alkyl-substituted indoles synthesis. The reaction can tolerate a variety of synthetically important functional groups (aryl-Br, aryl-I, heterocycle). The indole products can also be transformed into other important skeletons. Two bioactive compounds, i.e. indomethacin and pravadoline were prepared using the new method.
1. Rh催化酚酯导向C-H活化氧化Heck反应。我们首次实现酚酯导向的氧化Heck反应。反应可以有效的兼容Br, Cl等基团；多种烯烃底物都可以得到很好的反应。与Pd(Ⅱ)催化的Heck反应相比,反应实现很好的区域选择性控制。反应提供了合成2-烯基取代苯酚衍生物有效方法。
2. Rh催化C-H活化与联烯反应合成共轭烯烃反应。我们实现了Rh催化下C-H活化与联烯化合物反应合成共轭烯烃化合物。反应不仅可以实现烯烃C-H底物的反应,芳基C-H底物也可以得到很好的实现。反应产物可以转化为为其他重要骨架分子。
3.Rh催化C-H活化氰基化反应。首次实现了RRh(Ⅲ)催化下的C-H活化氰基化反应合成芳基腈化合物。反应使用NCTS作为氰基试剂来源,这是一种低毒易得的氰基化试剂。多种导向基都可以实现邻位的C-H活化氰基化反应；反应可以很好的兼容Br、I、酚羟基、环氧等重要的基团；芳香杂环底物也能得到很好的反应效果；反应可以实现复杂分子的C-H氰基化衍生。
4. Rh催化C-H活化合成2-甲基吲哚化合物。我们成功实现了Rh(Ⅲ)催化下,乙酰苯胺衍生物与烯丙醇酯反应得到2-甲基吲哚化合物。反应具有很好的官能团兼容性,Br、I、杂环等重要基团都可以很好的兼容；反应产物可以经过转化得到其他重要结构的化合物；并且我们实现了从简单酰胺原料出发合成两个重要的药物分子。
Transition-metal catalyzed C-H bond activation provides an atom-and step-economical approach for organic synthesis. A variety of transition metals (Pd, Ru, Ir, etc.) catalyzed C-H activation functionalization reaction have been developed. In the past five years, Rh (Ⅲ) catalyzed C-H activation reactions have been fully developed, and provides an effective method for the synthesis of biologically active compounds. This paper first reviews the Rh(III) catalyzed C-H activation functionalization reactions and application in the synthesis of heterocyclic. Notwithstanding these pioneering examples, further development of Rh(III) catalyzed C-H activation reactions reactions is needed in synthetic organic chemistry.
1. Rhodium-Catalyzed C-H Activation/Olefination of Phenol Carbamates. We reported a practical protocol for ortho C-H activation/olefination of phenol carbamates. The reaction tolerates a variety of important functional groups (aryl-Br, aryl-Cl) and many different olefins can be used in this process. This reaction exhibits different reactivity as compared to the Pd-catalyzed processes, this method provide a new approach for the synthesis of ortho-substituted phenols.
2. Rh-catalyzed C-H bond activation with allenes to produce highly unsaturated conjugated olefins. Rh(Ⅲ) catalyzed C-H bond activation with allenes to produce unsaturated conjuncted olefins was reported. The reaction is applicable to both olefin and arene C(Sp2)-H, compatible with varieties of functional groups. The obtained products can be transformed into other important skeletons.
3. Rhodium-catalyzed Directed C-H Cyanation. We report the first example of Rh-catalyzed directed C-H cyanation. N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS), a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this cyanation process and the reaction tolerates a variety of important functional groups (aryl-Br, aryl-I unprotected phenol, epoxide), A number of heteroaromatic nitriles were successfully synthesized by using this method, the reaction may provide a practical tool for rapid derivatization of bioactive compounds.
4. A practical Rh-catalyzed reaction was developed to achieve2-alkyl-substituted indoles synthesis. The reaction can tolerate a variety of synthetically important functional groups (aryl-Br, aryl-I, heterocycle). The indole products can also be transformed into other important skeletons. Two bioactive compounds, i.e. indomethacin and pravadoline were prepared using the new method.
引文
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[1](a) Kochanowska-Karamyan A J, Hamann M T. Marine indole alkaloids:Potential new drug leads for the control of depression and anxiety[J]. Chemical reviews,2010,110(8):4489-4497. (b) Bandini M, Eichholzer A. Catalytic functionalization of indoles in a new dimension[J]. Angewandte Chemie International Edition,2009,48(51):9608-9644. (c) Arisawa M, Kasaya Y, Obata T, et al. Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity[J]. Journal of medicinal chemistry,2012,55(18): 8152-8163.
[2](a) Cacchi S, Fabrizi G. Synthesis and functionalization of indoles through palladium-catalyzed reactions[J]. Chemical reviews,2005,105(7):2873-2920. (b) Humphrey G R, Kuethe J T. Practical methodologies for the synthesis of indoles[J]. Chemical reviews,2006,106(7):2875-2911. (c) Vicente R. Recent advances in indole syntheses:New routes for a classic target[J]. Organic & biomolecular chemistry,2011,9(19):6469-6480. (d) Inman M, Moody C J. Indole synthesis-something old, something new[J]. Chemical Science,2013,4(1):29-41.
[3]For Pd-catalyzed direct C-H indoles synthesis, see:(a) Tan Y, Hartwig J F. Palladium-Catalyzed Amination of Aromatic C-H Bonds with Oxime Esters[J]. Journal of the American Chemical Society, 2010,132(11):3676-3677. (b) Neumann J J, Rakshit S, Droege T, et al. Exploring the Oxidative Cyclization of Substituted N-Aryl Enamines:Pd-Catalyzed Formation of Indoles from Anilines[J]. Chemistry-A European Journal,2011,17(26):7298-7303. (c) Wei Y, Deb I, Yoshikai N. Palladium-Catalyzed Aerobic Oxidative Cyclization of N-Aryl Imines:Indole Synthesis from Anilines and Ketones[J]. Journal of the American Chemical Society,2012,134(22):9098-9101.
[4]For Rh-catalyzed direct C-H indoles synthesis, see:(a) Stuart D R, Bertrand-Laperle M, Burgess K M N, et al. Indole synthesis via rhodium catalyzed oxidative coupling of acetanilides and internal alkynes[J]. Journal of the American Chemical Society,2008,130(49):16474-16475. (b) Stuart D R, Alsabeh P, Kuhn M, et al. Rhodium (Ⅲ)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles[J]. Journal of the American Chemical Society,2010,132(51): 18326-18339. (c) Huestis M P, Chan L, Stuart D R, et al. The Vinyl Moiety as a Handle for Regiocontrol in the Preparation of Unsymmetrical 2,3-Aliphatic-Substituted Indoles and Pyrroles [J]. Angewandte Chemie,2011,123(6):1374-1377.
[5]For Cu-catalyzed direct C-H indoles synthesis, for see:(a) Bernini R, Fabrizi G. Sferrazza A, et al. Copper-Catalyzed C-C Bond Formation through C-H Functionalization:Synthesis of Multisubstituted Indoles from N-Aryl Enaminones[J]. Angewandte Chemie,2009,121(43): 8222-8225. (b) Li Y M, Sun M, Wang H L, et al. Direct Annulations toward Phosphorylated Oxindoles:Silver-Catalyzed Carbon-Phosphorus Functionalization of Alkenes[J]. Angewandte Chemie International Edition,2013,52(14):3972-3976.
[6]For Ru-catalyzed direct C-H indoles synthesis, see:Zhang T, Wu L, Li X. Rh (Ⅲ)-Catalyzed Olefination of N-Sulfonyl Imines:Synthesis of Ortho-Olefinated Benzaldehydes[J]. Organic letters, 2013,15(24):6294-6297.
[7]For Fe-catalyzed direct C-H indoles synthesis, see:Guan Z H, Yan Z Y, Ren Z H, et al. Preparation of indoles via iron catalyzed direct oxidative coupling[J]. Chemical Communications, 2010,46(16):2823-2825.
[8]For Au-catalyzed direct C-H indoles synthesis, see:Wang Y, Ye L, Zhang L. Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes[J]. Chemical Communications,2011,47(27):7815-7817.
[9]For Ni-catalyzed direct C-H indoles synthesis, see:Song W, Ackermann L. Nickel-catalyzed alkyne annulation by anilines:versatile indole synthesis by C-H/N-H functionalization[J]. Chemical Communications,2013,49(59):6638-6640.