Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

Peter Spannring; Vital A. Yazerski; Jianming Chen; Matthias Otte; Bert M. Weckhuysen; Pieter C A Bruijnincx; Robertus J M Klein Gebbink

doi:10.1002/ejic.201500213

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)₂(mix-BPBP)] and a Combination of H₂O₂ and NaIO₄

Peter Spannring
, Vital A. Yazerski
, Jianming Chen
, Matthias Otte
, Bert M. Weckhuysen
, Pieter C A Bruijnincx
, Robertus J M Klein Gebbink^*

^*Corresponding author for this work

Sub Organic Chemistry and Catalysis

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

Abstract

A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)₂(mix-BPBP)] with an oxidant combination of H₂O₂ (1.0 equiv.) and NaIO₄ (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)₂(mix-BPBP)], and the oxidants H₂O₂ and NaIO₄ can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

Original language	English
Pages (from-to)	3462-3466
Number of pages	5
Journal	European Journal of Inorganic Chemistry
Volume	2015
Issue number	21
DOIs	https://doi.org/10.1002/ejic.201500213
Publication status	Published - 1 Jul 2015

Keywords

Hydrogen peroxide
Iron
Olefin cleavage
Oxidation
Regioselectivity

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Spannring, P., Yazerski, V. A., Chen, J., Otte, M., Weckhuysen, B. M., Bruijnincx, P. C. A., & Klein Gebbink, R. J. M. (2015). Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)₂(mix-BPBP)] and a Combination of H₂O₂ and NaIO₄. European Journal of Inorganic Chemistry, 2015(21), 3462-3466. https://doi.org/10.1002/ejic.201500213

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title = "Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4",

abstract = "A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).",

keywords = "Hydrogen peroxide, Iron, Olefin cleavage, Oxidation, Regioselectivity",

author = "Peter Spannring and Yazerski, \{Vital A.\} and Jianming Chen and Matthias Otte and Weckhuysen, \{Bert M.\} and Bruijnincx, \{Pieter C A\} and \{Klein Gebbink\}, \{Robertus J M\}",

year = "2015",

month = jul,

day = "1",

doi = "10.1002/ejic.201500213",

language = "English",

volume = "2015",

pages = "3462--3466",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley",

number = "21",

}

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)₂(mix-BPBP)] and a Combination of H₂O₂ and NaIO₄. / Spannring, Peter; Yazerski, Vital A.; Chen, Jianming et al.
In: European Journal of Inorganic Chemistry, Vol. 2015, No. 21, 01.07.2015, p. 3462-3466.

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

TY - JOUR

T1 - Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)2(mix-BPBP)] and a Combination of H2O2 and NaIO4

AU - Spannring, Peter

AU - Yazerski, Vital A.

AU - Chen, Jianming

AU - Otte, Matthias

AU - Weckhuysen, Bert M.

AU - Bruijnincx, Pieter C A

AU - Klein Gebbink, Robertus J M

PY - 2015/7/1

Y1 - 2015/7/1

N2 - A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

AB - A method for the regioselective transformation of dienes to carbonyl compounds has been developed. Electron-rich olefins react selectively to yield valuable aldehydes and ketones. The method is based on the catalyst [Fe(OTf)2(mix-BPBP)] with an oxidant combination of H2O2 (1.0 equiv.) and NaIO4 (1.5 equiv.); it uses mild conditions and short reaction times, and it outperforms other olefin cleavage methodologies. The combination of an Fe-based catalyst, [Fe(OTf)2(mix-BPBP)], and the oxidants H2O2 and NaIO4 can discriminate between electronically different double bonds and oxidatively cleave the electron-rich bond in dienes to yield aldehydes and ketones in a regioselective manner. The reaction requires mild conditions (0-50 C) and short reaction times (70 min).

KW - Hydrogen peroxide

KW - Iron

KW - Olefin cleavage

KW - Oxidation

KW - Regioselectivity

UR - https://www.scopus.com/pages/publications/84938213059

U2 - 10.1002/ejic.201500213

DO - 10.1002/ejic.201500213

M3 - Article

SN - 1434-1948

VL - 2015

SP - 3462

EP - 3466

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 21

ER -

Regioselective Cleavage of Electron-Rich Double Bonds in Dienes to Carbonyl Compounds with [Fe(OTf)₂(mix-BPBP)] and a Combination of H₂O₂ and NaIO₄

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Keywords

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