A Microscale Heck Reaction In Water

TCE

The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 12 Issue 2 (2007) pp 77-79

A Microscale Heck Reaction In Water

Lawrence L. W. Cheung, Evangelos Aktoudianakis, Elton Chan, Amanda R. Edward, Isabel Jarosz, Vicki Lee, Leo Mui, Sonya S. Thatipamala and Andrew P. Dicks*

Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada, M5S 3H6, adicks@chem.utoronto.ca
Received June 7, 2006. Accepted March 12, 2007.

Published online: 1 April 2007

Abstract. This paper describes the Heck synthesis of (E)-4-acetylcinnamic acid from 4-iodoacetophenone and acrylic acid under catalysis by Pd (0). Traditional Heck reaction organic solvents (acetonitrile, N-methyl-2-pyrrolidone) and base (triethylamine) are replaced by water and sodium carbonate respectively. This approach introduces fundamentals of green chemistry to undergraduates whilst highlighting current research via an industrially significant reaction.

Key Words: Laboratories and Demonstrations; organic chemistry; microscale synthesis; aqueous reactivity; heck reaction; palladium catalysis

(*) Corresponding author. (E-mail: adicks@chem.utoronto.ca)

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Supporting Materials:

Laboratory notes for students (including experimental procedures and post-lab questions), additional notes for instructors (including a detailed reaction mechanism) and product spectroscopic information ((E)-4-acetylcinnamic acid ¹H and ¹³C NMR, MS, IR spectra and assignments) are available in a Zip file (274 KB).