Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies

Guo, Mian; Lee, Yong -Min; Seo, Mi Sook; Kwon, Yong -Ju; Li, Xiao -Xi; Ohta, Takehiro; Kim, Won -Suk; Sarangi, Ritimukta; Fukuzumi, Shunichi; Nam, Wonwoo

doi:10.1021/acs.inorgchem.8b01426

Title: Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies

Journal Article · Mon Aug 06 00:00:00 EDT 2018 · Inorganic Chemistry

DOI:https://doi.org/10.1021/acs.inorgchem.8b01426· OSTI ID:1476114

Guo, Mian ^[1];

^[1]; Seo, Mi Sook ^[1]; Kwon, Yong -Ju ^[1]; Li, Xiao -Xi ^[1];

^[2];

^[1];

^[3];

^[1];

^[4]

Ewha Womans Univ., Seoul (Korea)
Univ. of Hyogo, Hyogo (Japan)
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Ewha Womans Univ., Seoul (Korea); Shaanxi Normal Univ., Xi'an (People's Republic of China)

Mn(III)-iodosylarene porphyrin adducts, [Mn(III)(ArIO)(Porp)]⁺, were synthesized by reacting electron-deficient Mn(III) porphyrin complexes with iodosylarene (ArIO) at –60 °C and characterized using various spectroscopic methods. The [Mn(III)(ArIO)(Porp)]⁺ species were then investigated in the epoxidation of olefins under stoichiometric conditions. In the epoxidation of olefins by the Mn(III)-iodosylarene porphyrin species, epoxide was formed as the sole product with high chemoselectivities and stereoselectivities. For example, cyclohexene oxide was formed exclusively with trace amounts of allylic oxidation products; cis- and trans-stilbenes were oxidized to the corresponding cis- and trans-stilbene oxides, respectively. In the catalytic epoxidation of cyclohexene by an electron-deficient Mn(III) porphyrin complex and ^sPhIO at low temperature (e.g., –60 °C), the Mn(III)-iodosylarene porphyrin species was evidenced as the active oxidant that effects the olefin epoxidation to give epoxide as the product. However, at high temperature (e.g., 0 °C) or in the case of using an electron-rich manganese(III) porphyrin catalyst, allylic oxidation products, along with cyclohexene oxide, were yielded, indicating that the active oxidant(s) was not the Mn(III)-iodosylarene adduct but probably high-valent Mn-oxo species in the catalytic reactions. We also report the conversion of the Mn(III)-iodosylarene porphyrins to high-valent Mn-oxo porphyrins under various conditions, such as at high temperature, with electron-rich porphyrin ligand, and in the presence of base (OH–). The present study reports the first example of spectroscopically well-characterized Mn(III)-iodosylarene porphyrin species being an active oxidant in the stoichiometric and catalytic oxidation reactions. In conclusion other aspects, such as one oxidant versus multiple oxidants debate, also were discussed.

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Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-76SF00515; 2017R1D1A1B03032615; NRF-2010-00353; NRF-2012R1A3A2048842; 2017R1D1A1B03029982

OSTI ID:: 1476114

Journal Information:: Inorganic Chemistry, Vol. 57, Issue 16; ISSN 0020-1669

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 25 works

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