Poly(styrene) resin-supported cobalt(III) salen cyclic oligomers as active heterogeneous HKR catalysts

Michael G C Kahn, Joakim H. Stenlid, Marcus Weck

Research output: Contribution to journalArticle

Abstract

A cross-linked poly(styrene) support functionalized with cobalt(III) salen cyclic oligomers that can be used as a catalyst for the hydrolytic kinetic resolution (HKR) of terminal epoxides is reported. This catalyst is the most active heterogeneous catalyst to date for the HKR of terminal epoxides and can be recycled more than six times with excellent enantioselectivities for the HKR of epichlorohydrin. A 3-fold rate enhancement was observed when conducting the HKR reaction with 6 equivalents of water compared to 0.6 equivalents. We hypothesize that this rate enhancement is due to water sequestration of the diol product from the organic phase, thereby maintaining a high local concentration of epoxides and catalyst in the organic phase.

Original languageEnglish (US)
Pages (from-to)3016-3024
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number16
DOIs
StatePublished - Nov 12 2012

Fingerprint

Styrene
Cobalt
Oligomers
Epoxy Compounds
Resins
Catalysts
Kinetics
Epichlorohydrin
Water
Enantioselectivity
Catalyst supports
disalicylaldehyde ethylenediamine

Keywords

  • bimetallic catalysis
  • heterogeneous catalysis
  • recycling
  • supported catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Poly(styrene) resin-supported cobalt(III) salen cyclic oligomers as active heterogeneous HKR catalysts. / Kahn, Michael G C; Stenlid, Joakim H.; Weck, Marcus.

In: Advanced Synthesis and Catalysis, Vol. 354, No. 16, 12.11.2012, p. 3016-3024.

Research output: Contribution to journalArticle

@article{b18322e769b447338697820c60e83d56,
title = "Poly(styrene) resin-supported cobalt(III) salen cyclic oligomers as active heterogeneous HKR catalysts",
abstract = "A cross-linked poly(styrene) support functionalized with cobalt(III) salen cyclic oligomers that can be used as a catalyst for the hydrolytic kinetic resolution (HKR) of terminal epoxides is reported. This catalyst is the most active heterogeneous catalyst to date for the HKR of terminal epoxides and can be recycled more than six times with excellent enantioselectivities for the HKR of epichlorohydrin. A 3-fold rate enhancement was observed when conducting the HKR reaction with 6 equivalents of water compared to 0.6 equivalents. We hypothesize that this rate enhancement is due to water sequestration of the diol product from the organic phase, thereby maintaining a high local concentration of epoxides and catalyst in the organic phase.",
keywords = "bimetallic catalysis, heterogeneous catalysis, recycling, supported catalysis",
author = "Kahn, {Michael G C} and Stenlid, {Joakim H.} and Marcus Weck",
year = "2012",
month = "11",
day = "12",
doi = "10.1002/adsc.201200528",
language = "English (US)",
volume = "354",
pages = "3016--3024",
journal = "Advanced Synthesis and Catalysis",
issn = "1615-4150",
publisher = "Wiley-VCH Verlag",
number = "16",

}

TY - JOUR

T1 - Poly(styrene) resin-supported cobalt(III) salen cyclic oligomers as active heterogeneous HKR catalysts

AU - Kahn, Michael G C

AU - Stenlid, Joakim H.

AU - Weck, Marcus

PY - 2012/11/12

Y1 - 2012/11/12

N2 - A cross-linked poly(styrene) support functionalized with cobalt(III) salen cyclic oligomers that can be used as a catalyst for the hydrolytic kinetic resolution (HKR) of terminal epoxides is reported. This catalyst is the most active heterogeneous catalyst to date for the HKR of terminal epoxides and can be recycled more than six times with excellent enantioselectivities for the HKR of epichlorohydrin. A 3-fold rate enhancement was observed when conducting the HKR reaction with 6 equivalents of water compared to 0.6 equivalents. We hypothesize that this rate enhancement is due to water sequestration of the diol product from the organic phase, thereby maintaining a high local concentration of epoxides and catalyst in the organic phase.

AB - A cross-linked poly(styrene) support functionalized with cobalt(III) salen cyclic oligomers that can be used as a catalyst for the hydrolytic kinetic resolution (HKR) of terminal epoxides is reported. This catalyst is the most active heterogeneous catalyst to date for the HKR of terminal epoxides and can be recycled more than six times with excellent enantioselectivities for the HKR of epichlorohydrin. A 3-fold rate enhancement was observed when conducting the HKR reaction with 6 equivalents of water compared to 0.6 equivalents. We hypothesize that this rate enhancement is due to water sequestration of the diol product from the organic phase, thereby maintaining a high local concentration of epoxides and catalyst in the organic phase.

KW - bimetallic catalysis

KW - heterogeneous catalysis

KW - recycling

KW - supported catalysis

UR - http://www.scopus.com/inward/record.url?scp=84869029226&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84869029226&partnerID=8YFLogxK

U2 - 10.1002/adsc.201200528

DO - 10.1002/adsc.201200528

M3 - Article

VL - 354

SP - 3016

EP - 3024

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

IS - 16

ER -