Aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO2 coupling

M North; Sophie C Z Quek; Natalie E. Pridmore; Adrian C. Whitwood; Xiao Wu

doi:10.1021/acscatal.5b00235

Aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO₂ coupling

M North^*
, Sophie C Z Quek
, Natalie E. Pridmore
, Adrian C. Whitwood
, Xiao Wu

^*Corresponding author for this work

School of Chemistry

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

179 Citations (Scopus)

Abstract

The development of inexpensive and sustainable aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides is described. The kinetic resolution is carried out under mild conditions (0-25 °C and 1 bar of CO₂ pressure) in the presence of tetrabutylammonium bromide as co-catalyst in the absence of solvent. The relative rate of reaction of the two epoxide enantiomers (k_rel) is substrate dependent, and the highest k_rel obtained was 15.4, using N-(2,3-epoxypropyl)diphenylamine as substrate.

Original language	English
Pages (from-to)	3398-3402
Number of pages	5
Journal	ACS Catalysis
Volume	5
Issue number	6
DOIs	https://doi.org/10.1021/acscatal.5b00235
Publication status	Published - 5 Jun 2015

Keywords

aluminum(salen)
catalysis
cyclic carbonate
epoxide
kinetic resolution

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Cite this

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title = "Aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO2 coupling",

abstract = "The development of inexpensive and sustainable aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides is described. The kinetic resolution is carried out under mild conditions (0-25 °C and 1 bar of CO2 pressure) in the presence of tetrabutylammonium bromide as co-catalyst in the absence of solvent. The relative rate of reaction of the two epoxide enantiomers (krel) is substrate dependent, and the highest krel obtained was 15.4, using N-(2,3-epoxypropyl)diphenylamine as substrate.",

keywords = "aluminum(salen), catalysis, cyclic carbonate, epoxide, kinetic resolution",

author = "M North and Quek, \{Sophie C Z\} and Pridmore, \{Natalie E.\} and Whitwood, \{Adrian C.\} and Xiao Wu",

year = "2015",

month = jun,

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doi = "10.1021/acscatal.5b00235",

language = "English",

volume = "5",

pages = "3398--3402",

journal = "ACS Catalysis",

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TY - JOUR

T1 - Aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides via CO2 coupling

AU - North, M

AU - Quek, Sophie C Z

AU - Pridmore, Natalie E.

AU - Whitwood, Adrian C.

AU - Wu, Xiao

PY - 2015/6/5

Y1 - 2015/6/5

N2 - The development of inexpensive and sustainable aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides is described. The kinetic resolution is carried out under mild conditions (0-25 °C and 1 bar of CO2 pressure) in the presence of tetrabutylammonium bromide as co-catalyst in the absence of solvent. The relative rate of reaction of the two epoxide enantiomers (krel) is substrate dependent, and the highest krel obtained was 15.4, using N-(2,3-epoxypropyl)diphenylamine as substrate.

AB - The development of inexpensive and sustainable aluminum(salen) complexes as catalysts for the kinetic resolution of terminal epoxides is described. The kinetic resolution is carried out under mild conditions (0-25 °C and 1 bar of CO2 pressure) in the presence of tetrabutylammonium bromide as co-catalyst in the absence of solvent. The relative rate of reaction of the two epoxide enantiomers (krel) is substrate dependent, and the highest krel obtained was 15.4, using N-(2,3-epoxypropyl)diphenylamine as substrate.

KW - aluminum(salen)

KW - catalysis

KW - cyclic carbonate

KW - epoxide

KW - kinetic resolution

UR - https://www.scopus.com/pages/publications/84930653433

U2 - 10.1021/acscatal.5b00235

DO - 10.1021/acscatal.5b00235

M3 - Article (Academic Journal)

SN - 2155-5435

VL - 5

SP - 3398

EP - 3402

JO - ACS Catalysis

JF - ACS Catalysis

IS - 6

ER -