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

Abstract

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, andmore » 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.« less

Authors:
 [1]; ORCiD logo [1];  [1];  [1];  [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [3]; ORCiD logo [1]; ORCiD logo [4]
+ Show Author Affiliations
  1. Ewha Womans Univ., Seoul (Korea)
  2. Univ. of Hyogo, Hyogo (Japan)
  3. SLAC National Accelerator Lab., Menlo Park, CA (United States)
  4. Ewha Womans Univ., Seoul (Korea); Shaanxi Normal Univ., Xi'an (People's Republic of China)
Publication Date:
Research Org.:
SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1476114
Grant/Contract Number:  
AC02-76SF00515; 2017R1D1A1B03032615; NRF-2010-00353; NRF-2012R1A3A2048842; 2017R1D1A1B03029982
Resource Type:
Accepted Manuscript
Journal Name:
Inorganic Chemistry
Additional Journal Information:
Journal Volume: 57; Journal Issue: 16; Journal ID: ISSN 0020-1669
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Guo, Mian, Lee, Yong -Min, Seo, Mi Sook, Kwon, Yong -Ju, Li, Xiao -Xi, Ohta, Takehiro, Kim, Won -Suk, Sarangi, Ritimukta, Fukuzumi, Shunichi, and Nam, Wonwoo. Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies. United States: N. p., 2018. Web. doi:10.1021/acs.inorgchem.8b01426.
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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. Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies. United States. https://doi.org/10.1021/acs.inorgchem.8b01426
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Guo, Mian, Lee, Yong -Min, Seo, Mi Sook, Kwon, Yong -Ju, Li, Xiao -Xi, Ohta, Takehiro, Kim, Won -Suk, Sarangi, Ritimukta, Fukuzumi, Shunichi, and Nam, Wonwoo. Mon . "Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies". United States. https://doi.org/10.1021/acs.inorgchem.8b01426. https://www.osti.gov/servlets/purl/1476114.
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@article{osti_1476114,
title = {Mn(III)-Iodosylarene Porphyrins as an Active Oxidant in Oxidation Reactions: Synthesis, Characterization, and Reactivity Studies},
author = {Guo, Mian and Lee, Yong -Min and Seo, Mi Sook and Kwon, Yong -Ju and Li, Xiao -Xi and Ohta, Takehiro and Kim, Won -Suk and Sarangi, Ritimukta and Fukuzumi, Shunichi and Nam, Wonwoo},
abstractNote = {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.},
doi = {10.1021/acs.inorgchem.8b01426},
journal = {Inorganic Chemistry},
number = 16,
volume = 57,
place = {United States},
year = {Mon Aug 06 00:00:00 EDT 2018},
month = {Mon Aug 06 00:00:00 EDT 2018}
}
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