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,Rachel C Klet,Omar K Farha,M Hassan Beyzavi,Joseph T Hupp

doi:10.1063/1.4898359

Casey J Stephenson, Rachel C Klet + Show 3 more

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https://doi.org/10.1063/1.4898359

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Journal: APL materials	Publication Date: Oct 27, 2014
Citations: 10	License type: CC BY 3.0

Affiliation: Northwestern University, King Abdulaziz University

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.

Highlights

Research Update: A hafnium-based metalorganic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source
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
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

Summary

Introduction

Research Update: A hafnium-based metalorganic framework as a catalyst for regioselective ring-opening of epoxides with a mild hydride source. Farha1,2,a 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA 2Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia (Received 15 August 2014; accepted 3 September 2014; published online 27 October 2014) 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.

Results

Conclusion