Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid

Kaveh Farshadfar; Nina Gunawan; Farshad Shiri; James K. Howard; Andaravaas Patabadige Jude P. Vaas; Alex C. Bissember; Brian F. Yates; Jason A. Smith; Alireza Ariafard

doi:10.1021/acs.joc.2c01923

Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid

Kaveh Farshadfar, Nina Gunawan, Farshad Shiri, James K. Howard, Andaravaas Patabadige Jude P. Vaas, Alex C. Bissember, Brian F. Yates, Jason A. Smith^*, Alireza Ariafard

^*Corresponding author for this work

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Abstract

The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.

Original language	English
Pages (from-to)	13280–13287
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	87
Issue number	19
Early online date	26 Sept 2022
DOIs	https://doi.org/10.1021/acs.joc.2c01923
Publication status	Published - 7 Oct 2022
MoE publication type	A1 Journal article-refereed

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CHEM_Farshadfar_et_al_Discovery_of_Periodinane_2022_Journal_of_Organic_ChemistryAccepted author manuscript, 569 KBLicence: Unspecified

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Farshadfar, K., Gunawan, N., Shiri, F., Howard, J. K., Vaas, A. P. J. P., Bissember, A. C., Yates, B. F., Smith, J. A., & Ariafard, A. (2022). Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid. Journal of Organic Chemistry, 87(19), 13280–13287. https://doi.org/10.1021/acs.joc.2c01923

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title = "Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid",

abstract = "The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation. ",

author = "Kaveh Farshadfar and Nina Gunawan and Farshad Shiri and Howard, {James K.} and Vaas, {Andaravaas Patabadige Jude P.} and Bissember, {Alex C.} and Yates, {Brian F.} and Smith, {Jason A.} and Alireza Ariafard",

note = "Publisher Copyright: {\textcopyright} 2022 American Chemical Society.",

year = "2022",

month = oct,

day = "7",

doi = "10.1021/acs.joc.2c01923",

language = "English",

volume = "87",

pages = "13280–13287",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

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Farshadfar, K, Gunawan, N, Shiri, F, Howard, JK, Vaas, APJP, Bissember, AC, Yates, BF, Smith, JA & Ariafard, A 2022, 'Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid', Journal of Organic Chemistry, vol. 87, no. 19, pp. 13280–13287. https://doi.org/10.1021/acs.joc.2c01923

Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid. / Farshadfar, Kaveh; Gunawan, Nina; Shiri, Farshad et al.
In: Journal of Organic Chemistry, Vol. 87, No. 19, 07.10.2022, p. 13280–13287.

Research output: Contribution to journal › Article › Scientific › peer-review

TY - JOUR

T1 - Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid

AU - Farshadfar, Kaveh

AU - Gunawan, Nina

AU - Shiri, Farshad

AU - Howard, James K.

AU - Vaas, Andaravaas Patabadige Jude P.

AU - Bissember, Alex C.

AU - Yates, Brian F.

AU - Smith, Jason A.

AU - Ariafard, Alireza

PY - 2022/10/7

Y1 - 2022/10/7

N2 - The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.

AB - The 2-iodoxybenzoic acid (IBX)-controlled oxidative dearomatization of pyrroles occurs very slowly (or not all) in many organic solvents, including DMSO in which IBX is soluble. Interestingly, although IBX is only partially soluble in acetic acid, this solvent mediates the pyrrole oxidative dearomatization. With the aid of density functional theory (DFT) calculations, we have discovered a new mode of reactivity, termed the periodinane oxy-assisted (POA) oxidation mechanism, which explains this observation.

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U2 - 10.1021/acs.joc.2c01923

DO - 10.1021/acs.joc.2c01923

M3 - Article

AN - SCOPUS:85139202213

SN - 0022-3263

VL - 87

SP - 13280

EP - 13287

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 19

ER -

Discovery of Periodinane Oxy-Assisted (POA) Oxidation Mechanism in the IBX-Controlled Oxidative Dearomatization of Pyrroles Mediated by Acetic Acid

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