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A Multistep Synthesis of 4-Nitro-1-ethynylbenzene Involving Palladium Catalysis, Conformational Analysis, Acetal Hydrolysis, and Oxidative Decarbonylation
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Abstract
Palladium-catalyzed reactions, particularly carbon-carbon bond formations, are rapidly becoming a mainstay of organic synthesis in industrial and academic laboratories. Although these important procedures are covered in advanced organic chemistry texts, they have rarely permeated into introductory organic texts or laboratory manuals. One of the more useful processes involves the coupling of a terminal alkyne to an aromatic bromide or iodide. We describe a convenient coupling procedure for the preparation of the tetrahydropyranyl ether of a propargyl alcohol derivative. This product can be easily hydrolyzed to the propargyl alcohol, then oxidatively decarbonylated to produce 4-nitro-1-ethynylbenzene. Several important topics may be illustrated and discussed in conjunction with the multistep microscale reaction series which has been developed. These include the following: palladium-catalyzed carbon-carbon bond formation, conformational analysis by NMR spectroscopy and molecular modeling, hydrolysis of an acetal, and oxidative decarbonylation via nucleophilic acyl substitution.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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- Received: August 03, 2009
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