Research update

A hafnium-based metal-organic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source

Casey J. Stephenson, M. Hassan Beyzavi, Rachel C. Klet, Joseph T Hupp, Omar K. Farha

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Reaction of styrene oxide with sodium cyanoborohydride and a catalytic amount of Hf-NU-1000 yields the anti-Markovnikov product, 2-phenylethanol, with over 98% regioselectivity. On the other hand, propylene oxide is ring opened in a Markovnikov fashion to form 2-propanol with 95% regioselectivity. Both styrene oxide and propylene oxide failed to react with sodium cyanoborohydride without the addition of Hf-NU-1000 indicative of the crucial role of Hf-NU-1000 as a catalyst in this reaction. To the best of our knowledge, this is the first report of the use of a metal-organic framework material as a catalyst for ring-opening of epoxides with hydrides.

Original languageEnglish
Article number123901
JournalAPL Materials
Volume2
Issue number12
DOIs
Publication statusPublished - Dec 1 2014

Fingerprint

styrene oxide
Hafnium
Regioselectivity
Epoxy Compounds
Hydrides
Metals
Phenylethyl Alcohol
Catalysts
Oxides
2-Propanol
Propylene
Styrene
Sodium
Propanol
sodium cyanoborohydride
propylene oxide

ASJC Scopus subject areas

  • Materials Science(all)
  • Engineering(all)

Cite this

Research update : A hafnium-based metal-organic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source. / Stephenson, Casey J.; Hassan Beyzavi, M.; Klet, Rachel C.; Hupp, Joseph T; Farha, Omar K.

In: APL Materials, Vol. 2, No. 12, 123901, 01.12.2014.

Research output: Contribution to journalArticle

@article{e96a3bc0e1c540ec8dc17ee1ddc19bc4,
title = "Research update: A hafnium-based metal-organic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source",
abstract = "Reaction of styrene oxide with sodium cyanoborohydride and a catalytic amount of Hf-NU-1000 yields the anti-Markovnikov product, 2-phenylethanol, with over 98{\%} regioselectivity. On the other hand, propylene oxide is ring opened in a Markovnikov fashion to form 2-propanol with 95{\%} regioselectivity. Both styrene oxide and propylene oxide failed to react with sodium cyanoborohydride without the addition of Hf-NU-1000 indicative of the crucial role of Hf-NU-1000 as a catalyst in this reaction. To the best of our knowledge, this is the first report of the use of a metal-organic framework material as a catalyst for ring-opening of epoxides with hydrides.",
author = "Stephenson, {Casey J.} and {Hassan Beyzavi}, M. and Klet, {Rachel C.} and Hupp, {Joseph T} and Farha, {Omar K.}",
year = "2014",
month = "12",
day = "1",
doi = "10.1063/1.4898359",
language = "English",
volume = "2",
journal = "APL Materials",
issn = "2166-532X",
publisher = "American Institute of Physics Publising LLC",
number = "12",

}

TY - JOUR

T1 - Research update

T2 - A hafnium-based metal-organic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source

AU - Stephenson, Casey J.

AU - Hassan Beyzavi, M.

AU - Klet, Rachel C.

AU - Hupp, Joseph T

AU - Farha, Omar K.

PY - 2014/12/1

Y1 - 2014/12/1

N2 - Reaction of styrene oxide with sodium cyanoborohydride and a catalytic amount of Hf-NU-1000 yields the anti-Markovnikov product, 2-phenylethanol, with over 98% regioselectivity. On the other hand, propylene oxide is ring opened in a Markovnikov fashion to form 2-propanol with 95% regioselectivity. Both styrene oxide and propylene oxide failed to react with sodium cyanoborohydride without the addition of Hf-NU-1000 indicative of the crucial role of Hf-NU-1000 as a catalyst in this reaction. To the best of our knowledge, this is the first report of the use of a metal-organic framework material as a catalyst for ring-opening of epoxides with hydrides.

AB - Reaction of styrene oxide with sodium cyanoborohydride and a catalytic amount of Hf-NU-1000 yields the anti-Markovnikov product, 2-phenylethanol, with over 98% regioselectivity. On the other hand, propylene oxide is ring opened in a Markovnikov fashion to form 2-propanol with 95% regioselectivity. Both styrene oxide and propylene oxide failed to react with sodium cyanoborohydride without the addition of Hf-NU-1000 indicative of the crucial role of Hf-NU-1000 as a catalyst in this reaction. To the best of our knowledge, this is the first report of the use of a metal-organic framework material as a catalyst for ring-opening of epoxides with hydrides.

UR - http://www.scopus.com/inward/record.url?scp=84908428778&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84908428778&partnerID=8YFLogxK

U2 - 10.1063/1.4898359

DO - 10.1063/1.4898359

M3 - Article

VL - 2

JO - APL Materials

JF - APL Materials

SN - 2166-532X

IS - 12

M1 - 123901

ER -