Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex

Ramona Turcas, Dóra Lakk-Bogáth, G. Speier, J. Kaizer

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45% enantiomeric excess (ee).

Original languageEnglish
Pages (from-to)141-144
Number of pages4
JournalInorganic Chemistry Communications
Volume92
DOIs
Publication statusPublished - Jun 1 2018

Fingerprint

Cyclohexanones
Enantioselectivity
Derivatives
Oxidation
oxidation
Kinetics
kinetics
Rate constants
Ligands
ligands
cyclohexanone

Keywords

  • Baeyer-Villiger oxidation
  • Biomimetics
  • Enantioselectivity
  • Iron(IV)-oxo complex
  • Kinetics

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex. / Turcas, Ramona; Lakk-Bogáth, Dóra; Speier, G.; Kaizer, J.

In: Inorganic Chemistry Communications, Vol. 92, 01.06.2018, p. 141-144.

Research output: Contribution to journalArticle

@article{d9c9ab6a483942a9b076b749a9b7d461,
title = "Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex",
abstract = "The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45{\%} enantiomeric excess (ee).",
keywords = "Baeyer-Villiger oxidation, Biomimetics, Enantioselectivity, Iron(IV)-oxo complex, Kinetics",
author = "Ramona Turcas and D{\'o}ra Lakk-Bog{\'a}th and G. Speier and J. Kaizer",
year = "2018",
month = "6",
day = "1",
doi = "10.1016/j.inoche.2018.04.024",
language = "English",
volume = "92",
pages = "141--144",
journal = "Inorganic Chemistry Communication",
issn = "1387-7003",
publisher = "Elsevier BV",

}

TY - JOUR

T1 - Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex

AU - Turcas, Ramona

AU - Lakk-Bogáth, Dóra

AU - Speier, G.

AU - Kaizer, J.

PY - 2018/6/1

Y1 - 2018/6/1

N2 - The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45% enantiomeric excess (ee).

AB - The previously reported oxoiron(IV) complex, [FeIV(asN4Py)(O)]2+ with chiral pentadentate ligand, asN4Py (asN4Py = N,N‑bis(2‑pyridylmethyl)‑1,2‑di(2‑pyridyl)ethylamine), is effective for the Baeyer-Villiger oxidation of cyclohexanone derivatives. The reaction is shown to be first order in both cyclohexanone and the oxoiron(IV) species. The second order rate constant is smaller by one order of magnitude than that obtained for the related achiral [FeIV(N4Py)(O)]2+ complex. Oxidation of 4-substituted cyclohexanone derivatives by the chiral oxoiron(IV) complex attains moderate enantioselectivities up to 45% enantiomeric excess (ee).

KW - Baeyer-Villiger oxidation

KW - Biomimetics

KW - Enantioselectivity

KW - Iron(IV)-oxo complex

KW - Kinetics

UR - http://www.scopus.com/inward/record.url?scp=85046159902&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85046159902&partnerID=8YFLogxK

U2 - 10.1016/j.inoche.2018.04.024

DO - 10.1016/j.inoche.2018.04.024

M3 - Article

AN - SCOPUS:85046159902

VL - 92

SP - 141

EP - 144

JO - Inorganic Chemistry Communication

JF - Inorganic Chemistry Communication

SN - 1387-7003

ER -