钯催化C—H键官能团化形成C—X (X=O, N, F, I, ……)键的密度泛函理论研究进展

doi:10.6023/cjoc202110027

摘要/Abstract

过渡金属催化C—H键官能团化是形成C—X (X=O, N, F, I, ……)键的有效方法, 在传统有机合成、农药、医药以及构筑含C—X杂环的生物活性天然产物基本骨架方面都扮演着重要角色. 钯催化C—H键官能团化形成C—X键的方法具有反应效率高、原子经济性好、环境友好等优点, 是近年来过渡金属催化构建C—X键的研究热点. 采用密度泛函理论(DFT)对钯催化C—H键官能团化形成C—X键的反应开展理论研究, 可获取有关反应路径的诸多信息, 帮助人们从微观层面深入认识此类反应的微观机理和反应选择性调控机制, 为改进钯催化C—H键官能团化形成C—X键的选择性和反应性控制拓展新思路. 对近十年来钯催化C—H键官能团化形成C—X (X=O, N, F, I, ……)键的最新理论研究进展进行了综述, 对上述反应的微观机理和反应选择性进行了深入探讨, 并对该领域的现存问题和发展前景进行了总结与展望.

关键词: 钯催化, C—H键官能团化, C—X键形成, 反应机理, 选择性, 密度泛函理论(DFT)

Transition metal-catalyzed C—H functionalization is an effective method for constructing C—X (X=O, N, F, I, …) bonds, which plays a crucial role not only in traditional organic synthesis, pesticides and medicine areas, but also in generating skeletons of biologically active natural products containing C—X heterocycles. Due to its high reaction efficiency, good atomic economy and environmental friendliness, palladium-catalyzed C—H functionalization has been demonstrated as one of the focus topics in the field of transition metal-catalyzed construction of C—X bonds for decades. Based on previous experimental results, density functional theory (DFT) has been employed to study the palladium-catalyzed C—H functionalization for constructing C—X bonds in detail, for obtaining more information about reaction process, such as microscopic reaction mechanism and selectivity regulation principles, and thus inspire new ideas for improving the selectivity and reactivity of palladium-catalyzed C—H functionalization in constructing C—X bonds. Herein, the latest density functional theory research results on palladium-catalyzed C—H functionalization in constructing C—X (X=O, N, F, I, …) bonds are summarized, with emphasis on the corresponding computational results about microcosmic reaction mechanism and selectivity controlling. The present issues and prospects of future development in this field are also summarized and forecasted in the end.

Key words: Pd catalysis, C—H functionalization, C—X bonds formation, reaction mechanism, selectivity, density functional theory (DFT)

引用此文

石宇冰, 白文己, 母伟花, 李江平, 于嘉玮, 连冰. 钯催化C—H键官能团化形成C—X (X=O, N, F, I, ……)键的密度泛函理论研究进展[J]. 有机化学, 2022, 42(5): 1346-1374.

Yubing Shi, Wenji Bai, Weihua Mu, Jiangping Li, Jiawei Yu, Bing Lian. Research Progress on Density Functional Theory Study of Palladium-Catalyzed C—H Functionalization to Form C—X (X=O, N, F, I, …) Bonds[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1346-1374.

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图/表 41

图1. 钯催化N-甲氧基苯甲酰胺(R1)直接烷氧基化反应的势能剖面图(a)和ISRE/OSRE过渡态的结构(b)

Figure 1. (a) Potential energy profiles for Pd-catalyzed direct alkoxylation of N-methoxybenzamide (R1), and (b) the structures of transition states for ISRE and OSRE processes

图2. 钯催化苯基叔丁醇(R2) C(sp2)—H活化/C—O偶联反应的势能剖面图

Figure 2. Potential energy profiles for Pd-catalyzed C(sp2)—H activation/C—O coupling of phenyl-tert-butanol (R2)

图3. 钯和钌催化苯甲酰苯胺(R3) C(sp2)—H活化反应及其四种过渡态结构

Figure 3. Pd and Ru-catalyzed C(sp2)—H activation of benzanilide (R3) and its four transition state structures

图4. 钯催化酯(R4)间位羟基化反应的势能剖面图

Figure 4. Potential energy profiles for Pd-catalyzed meta-hydroxylation reaction of ester (R4)

图5. 钯催化萘酮(R5)与N-氟-1,3,5-三甲基吡啶三氟酸盐(R6) C—H活化/C8-三氟化或氟化反应的势能剖面图

Figure 5. Potential energy profiles for Pd-catalyzed C—H activation/C8-triflation or fluorination reaction of naphthylketone (R5) with N-fluoro-1,3,5-trimethylpyridinium triflate (R6)

图6. 钯催化邻溴苯甲醛(R7)与芳基重氮酯(R8)分子间酰基化反应的势能剖面图

Figure 6. Potential energy profiles for Pd-catalyzed intermolecular acylation of ortho-bromobenzaldehyde (R7) with aryldiazoester (R8)

图7. 钯催化peri-氧化反应和ortho-氧化反应的势能剖面图

Figure 7. Potential energy profiles for Pd-catalyzed peri-oxygenation and ortho-oxygenation

图8. 钯催化级联C—H活化步骤的势能剖面图(能量: kJ•mol–1)

Figure 8. Potential energy profiles for Pd-catalyzed cascade C—H activation step (energy in kJ•mol–1)

图9. 钯催化N-芳基苯甲酰胺(R11)与o-苯甲酰羟胺(R12)的分子间邻位C—H胺化反应[79]及其三种C—H活化过渡态结构[80]

Figure 9. Pd-catalyzed intermolecular o-C—H amination of N-arylbenzamide (R11) with o-benzoyl hydroxylamine (R12)[79], and its three C—H activation transition state tructures[80]

图10. 钯催化N-芳基苯甲酰胺邻位胺化反应的势能剖面图

Figure 10. Potential energy profiles for Pd-catalyzed ortho-amination of N-arylbenzamide

图11. 钯催化N-芳基苯甲酰胺(R11)与o-苯甲酰羟胺(R15)分子间C—H胺化反应的势能剖面图

Figure 11. Potential energy profiles for Pd-catalyzed intermolecular C—H amination of N-arylbenzamide (R11) with o-benzoylhydroxylamine (R15)

图12. 钯催化N-苄基吡啶酰胺(R16)与PhI(OAc)2/PhI(DMM)的分子内C—H胺化反应的计算结果

Figure 12. Computational results about Pd-catalyzed intramolecular C—H amination of N-benzylpicolinamides (R16) with PhI(OAc)2 or PhI(DMM)

图13. 钯催化AcO-NH(COR)与苯的C—H胺化反应及其“吖啶效应”根源的计算结果

Figure 13. Pd-catalyzed C—H amination of AcO-NH(COR) with benzene and computational results about the origin of the “acridine effect”

图14. 二叔丁基二氮杂环丙烷酮(R19) N—N键氧化加成步骤的部分势能剖面图

Figure 14. Partial potential energy profiles for N—N bond oxidation addition step of di-tert-butyldiaziridinone (R19)

图15. 钯催化芳基吡唑ortho-C—H氟化反应的部分势能剖面图

Figure 15. Partial potential energy profiles for the Pd-catalyzed ortho-C—H fluorination of arylpyrazole

图16. 芳基-Pd(II)-NOx催化偶氮苯(R20)选择性C—H氟化反应及其中间体INT91-INT93还原消除过程的计算结果

Figure 16. Aryl-Pd(II)-NOx-catalyzed selective C—H fluorination of azobenzene (R20) and computational results about reductive elimination processes of the intermediate INT91-INT93

图17. 钯催化N-芳基酰胺C—H碘化反应的部分势能剖面图

Figure 17. Partial potential energy profiles for Pd-catalyzed C—H iodization of N-aryl amide

图18. 钯催化苄胺ortho-C—H碘化反应的势能剖面图

Figure 18. Potential energy profiles for Pd-catalyzed ortho-C—H iodization of benzyl amine

图19. 钯催化萘基亚砜(R23) peri-C—H活化的势能剖面图

Figure 19. Potential energy profiles for Pd-catalyzed peri-C—H activation of naphthyl sulfoxide (R23)

图20. 钯催化苯与1-苯硫基-吡咯啉-2,5-二酮(R24)的芳基硫醇化反应的势能剖面图

Figure 20. Potential energy profiles for Pd-catalyzed arylthiolation of benzene with 1-(phenylthio) pyrrolidine-2,5-dione (R24)

图21. 钯催化C—H硅烷化/硼化反应及六元氧代钯环中间体INT138形成的势能剖面图

Figure 21. Pd-catalyzed C—H silylation/boration reaction and potential energy profiles for the formation of six-membered oxo-palladacycle intermediate INT138

图22. 钯催化C—H键官能团化形成C—Zn键的势能剖面图

Figure 22. Potential energy profiles for Pd-catalyzed C—H functionalization to form C—Zn bond

图23. 钯催化亚甲基C(sp3)—H活化/甲氧基化反应机理及两种可能的过渡态结构

Figure 23. Mechanism of Pd-catalyzed methylene C(sp3)—H activation/methoxylation and two possible transition state structures

图24. 钯催化甲烷C—H键官能团化形成三氟乙酸甲酯(P25)的势能剖面图

Figure 24. Potential energy profiles for Pd-catalyzed C—H functionalization of methane to form methyl trifluoroacetate (P25)

图25. 钯催化1-氨基蒽醌酰胺(R28) α-C(sp3)—H活化/乙酰氧基化反应的势能剖面图

Figure 25. Potential energy profiles for Pd-catalyzed α-C(sp3)—H activation/acetoxylation of 1-aminoanthraquinone amide (R28)

图26. C(sp3)—OAc和C(sp3)—C(sp2)键形成的部分势能剖面图

Figure 26. Partial potential energy profiles for C(sp3)—OAc and C(sp3)—C(sp2) bond formation

图27. 钯催化吗啉酮γ-C(sp3)—H活化/乙酰氧基化反应的势能剖面图

Figure 27. Potential energy profiles for Pd-catalyzed γ-C(sp3)—H activation/acetoxylation of morpholinone

表1. 苯胺非活化C(sp3)—H键的胺化反应及其三种可能的氧化加成中间体结构

图式1. 钯催化8-甲基喹啉(R30)分子间C(sp3)—H酰胺化反应的催化循环

Scheme 1. Catalytic cycle of Pd-catalyzed intermolecular C(sp3)—H amidation of 8-methylquinoline (R30)

图28. 钯催化脂肪胺(R31)的C(sp3)—H活化反应的部分势能剖面图[112]

Figure 28. Partial potential energy profiles for Pd-catalyzed C(sp3)—H activation of aliphatic amines (R31)[112]

图29. 钯催化脂肪胺(R31)的C(sp3)—H活化反应的势能剖面图[113]

Figure 29. Potential energy profiles for Pd-catalyzed C(sp3)—H activation of aliphatic amines (R31)[113]

图式2. 钯催化四甲基吗啉酮(R32)的氮杂环丙烷化反应的催化循环

Scheme 2. Catalytic cycle of Pd-catalyzed aziridination of tetramethylmorpholinone (R32)

图30. 钯催化四甲基吗啉酮(R32)的氮杂环丙烷化反应的部分势能剖面图

Figure 30. Partial potential energy profiles for Pd-catalyzed aziridination of tetramethylmorpholinone (R32)

图式3. 钯催化丁基-3-烯基-N-甲苯磺酰基氨基甲酸酯(R33)直接分子内烯丙基胺化反应的计算结果

Scheme 3. Computational results about Pd-catalyzed direct intramolecular allylic amination of but-3-enyl-N-tosyl carbamate (R33)

图式4. 钯催化3-芳基丙胺(R34)对映选择性分子内C(sp3)—H酰胺化反应及其两种可能的过渡态结构

Scheme 4. Pd-catalyzed enantioselective intramolecular C(sp3)—H amidation of 3-arylpropylamine (R34) and its two possible transition state structures

图31. 钯催化酰胺C(sp3)—H氟化反应的势能剖面图

Figure 31. Potential energy profiles for Pd-catalyzed C(sp3)—H fluorination of amide

图32. 钯催化游离胺亚甲基γ-C(sp3)—H氟化反应的势能剖面图

Figure 32. Potential energy profiles for Pd-catalyzed methylene γ-C(sp3)—H fluorination of free amine

图33. 钯催化游离胺甲基γ-C(sp3)—H氟化反应的势能剖面图

Figure 33. Potential energy profiles for Pd-catalyzed methyl γ-C(sp3)—H fluorination of free amine

图34. 钯催化噁唑啉C—H活化的部分势能剖面图

Figure 34. Partial potential energy profiles for Pd-catalyzed C—H activation of oxazoline

图35. 钯催化远端γ-C(sp3)—H硅烷化和锗化的势能剖面图

Figure 35. Potential energy profiles for Pd-catalyzed remote γ-C(sp3)—H silylation and germanylation

图36. 钯催化β-C(sp3)—H硼化反应的势能剖面图

Figure 36. Potential energy profiles for Pd-catalyzed methyl β-C(sp3)—H borylation

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