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The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst
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Abstract
Palladium catalysts are central to a large variety of modern organic syntheses. Heck reactions use palladium acetate as the preferred precatalyst to effect vinylic substitutions involving haloarenes and haloalkenes. The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy. This experiment is appropriate for a second-semester introductory organic chemistry laboratory or an intermediate-level organic synthesis laboratory. It could be adapted as a project for two or three students, with each member of the group preparing a different isomer or using a different catalyst source.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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This article has been cited by 4 ACS Journal articles (4 most recent appear below).
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- Received: August 03, 2009
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