Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity

John Gullick; Sophia Taylor; Paul McMorn; Donald Bethell; Philip C. Bulman Page; Frederick E. Hancock; Frank King; Graham J. Hutchings

doi:10.1016/S1381-1169(01)00497-6

Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity

John Gullick, Sophia Taylor, Paul McMorn, Donald Bethell, Philip C. Bulman Page, Frederick E. Hancock, Frank King, Graham J. Hutchings

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

14 Citations (Scopus)

Abstract

The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf)(2)) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [N-(p-nitrophenyisulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions. (C) 2002 Elsevier Science B.V. All rights reserved.

Original language	English
Pages (from-to)	571-575
Number of pages	5
Journal	Journal of Molecular Catalysis A: Chemical
Volume	182-183
DOIs	https://doi.org/10.1016/S1381-1169(01)00497-6
Publication status	Published - 31 May 2002

Keywords

OLEFINS
ANISOLE
styrene aziridination
donors
SOLID SOLVENTS
ZEOLITE CATALYSTS
FINE CHEMICALS SYNTHESIS
nitrene
bis(oxazoline)-modified CuHY zeolite

Access to Document

10.1016/S1381-1169(01)00497-6

Cite this

Gullick, J., Taylor, S., McMorn, P., Bethell, D., Bulman Page, P. C., Hancock, F. E., King, F., & Hutchings, G. J. (2002). Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity. Journal of Molecular Catalysis A: Chemical, 182-183, 571-575. https://doi.org/10.1016/S1381-1169(01)00497-6

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title = "Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity",

abstract = "The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf)(2)) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [N-(p-nitrophenyisulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions. (C) 2002 Elsevier Science B.V. All rights reserved.",

keywords = "OLEFINS, ANISOLE, styrene aziridination, donors, SOLID SOLVENTS, ZEOLITE CATALYSTS, FINE CHEMICALS SYNTHESIS, nitrene, bis(oxazoline)-modified CuHY zeolite",

author = "John Gullick and Sophia Taylor and Paul McMorn and Donald Bethell and {Bulman Page}, {Philip C.} and Hancock, {Frederick E.} and Frank King and Hutchings, {Graham J.}",

year = "2002",

month = may,

day = "31",

doi = "10.1016/S1381-1169(01)00497-6",

language = "English",

volume = "182-183",

pages = "571--575",

journal = "Journal of Molecular Catalysis A: Chemical",

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Gullick, J, Taylor, S, McMorn, P, Bethell, D, Bulman Page, PC, Hancock, FE, King, F & Hutchings, GJ 2002, 'Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity', Journal of Molecular Catalysis A: Chemical, vol. 182-183, pp. 571-575. https://doi.org/10.1016/S1381-1169(01)00497-6

Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity. / Gullick, John; Taylor, Sophia; McMorn, Paul et al.
In: Journal of Molecular Catalysis A: Chemical, Vol. 182-183, 31.05.2002, p. 571-575.

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

TY - JOUR

T1 - Heterogeneous aziridination of styrene using N-(p-nitrophenylsulfonyl)imino phenyliodinane as nitrene donor: influence of the reaction parameters on yield and enantioselectivity

AU - Gullick, John

AU - Taylor, Sophia

AU - McMorn, Paul

AU - Bethell, Donald

AU - Bulman Page, Philip C.

AU - Hancock, Frederick E.

AU - King, Frank

AU - Hutchings, Graham J.

PY - 2002/5/31

Y1 - 2002/5/31

N2 - The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf)(2)) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [N-(p-nitrophenyisulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions. (C) 2002 Elsevier Science B.V. All rights reserved.

AB - The copper-catalysed aziridination of styrene with copper-exchanged zeolite Y (CuHY) and copper(II) triflate (Cu(OTf)(2)) as catalysts is described and discussed. In particular, the effects of reaction conditions on the yield and enantiomeric excess of the aziridine product are described using [N-(p-nitrophenyisulfonyl)imino]phenyliodinane (PhI=NNs) as nitrene donor. By careful control of the styrene:nitrene donor molar ratio and the solvent, an ee of 95% can be obtained for the heterogeneously catalysed bis(oxazoline)-modified zeolite CuHY The ee achieved with the zeolite immobilised catalyst is significantly higher than that achieved for the non-immobilised homogeneous catalyst under comparable reaction conditions. (C) 2002 Elsevier Science B.V. All rights reserved.

KW - OLEFINS

KW - ANISOLE

KW - styrene aziridination

KW - donors

KW - SOLID SOLVENTS

KW - ZEOLITE CATALYSTS

KW - FINE CHEMICALS SYNTHESIS

KW - nitrene

KW - bis(oxazoline)-modified CuHY zeolite

U2 - 10.1016/S1381-1169(01)00497-6

DO - 10.1016/S1381-1169(01)00497-6

M3 - Article

SN - 1381-1169

VL - 182-183

SP - 571

EP - 575

JO - Journal of Molecular Catalysis A: Chemical

JF - Journal of Molecular Catalysis A: Chemical

ER -