Citation: Zi-Hao WEN, Shuang LI, Min-Yi ZHANG. Theoretical Study of Non-heme Mn(Ⅴ)-oxo Complexes: Formation Mechanism, Electronic Nature, and Hydroxylation Reactivity[J]. Chinese Journal of Structural Chemistry, ;2021, 40(12): 1557-1566. doi: 10.14102/j.cnki.0254-5861.2011-3209 shu

Theoretical Study of Non-heme Mn(Ⅴ)-oxo Complexes: Formation Mechanism, Electronic Nature, and Hydroxylation Reactivity

Zi-Hao WEN ^{a, b} ,
Shuang LI ^b ,
Min-Yi ZHANG ^b,,

a.
College of Chemistry and Material Science, Fujian Normal University, Fuzhou 350007, China
b.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

Corresponding author: Min-Yi ZHANG, myzhang@fjirsm.ac.cn
Received Date: 2 April 2021
Accepted Date: 7 May 2021

Figures(8)

Many non-heme manganese complexes exhibit high reactivity and enantioselectivity for the activation of C–H bonds. Recently, Mn(PDP) complexes (PDP = N,N΄-bis(pyridine-2-ylmethyl)-2,2΄-bipyrrolidine) have been reported to activate C–H bonds selectively in the presence of carboxylic acids. In this study, we performed density functional theory calculations to investigate the formation and hydroxylation mechanisms of Mn(PDP) complexes. Our calculation results showed that Mn(Ⅲ)(PDP) complexes react with H₂O₂ and carboxylic acid to form Mn(Ⅴ)-oxo oxidation intermediate. The main oxidation intermediate, [(PDP)Mn(Ⅳ)(O···OC(O)CH₃)^2-·]²⁺, was found to have the characteristics of S(Mn) = 3/2 manganese(Ⅳ) center antiferromagnetically coupled to a σ^*_O–O radical, where the O–O bond is not completely broken. Furthermore, [(PDP)Mn(Ⅳ)(O···OC(O)CH₃)^2-·]²⁺ was shown to have two single electron-accepting orbitals (α Mn-d_xy and β σ^*_O–O) that can simultaneously interact with a doubly occupied electron-donating orbital (σ_C–H) of substrate. Therefore, [(PDP)Mn(Ⅳ)(O···OC(O)CH₃)^2-·]²⁺ species can act as a two-electron oxidant for the C−H bond functionalization. As a result, the C−H bond hydroxylation by [(PDP)Mn(Ⅳ)(O···OC(O)CH₃)^2-·]²⁺ species was a single step. Following the H-abstraction with a low barrier of 4.5 kcal/mol, hydroxyl group would immediately rebound to the radical carbon without barrier. These results provide new insights toward the further development of non-heme manganese catalysts.
- C–H bond activation,
- non-heme manganese complex,
- homogeneous catalysis,
- density functional theory calculations
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