Research Progress on Density Functional Theory Study of Palladium-Catalyzed C—H Functionalization to Form C—X (X=O, N, F, I, …) Bonds

doi:10.6023/cjoc202110027

Abstract

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)

Cite this article

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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Fig. & Tab. 41

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

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

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

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

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)

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

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

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

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]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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