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Synthesis of 4-Nitro-1-Pentynylbenzene: An Example of Transitional Metal-Mediated Cross-Coupling
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Abstract
A procedure for the preparation and purification of 4-nitro-1-pentynylbenzene is reported for use as an introductory organic laboratory exercise. Synthesis of the target compound exemplifies contemporary Pd-mediated cross-coupling methodologies. In this regard, several fundamental mechanistic aspects of catalytic organometallic chemistry are illustrated, including oxidative addition, transmetallation, and reductive elimination. Purification of the target compound via flash column chromatography exposes students to a central technique of modern synthetic methodology. Spectroscopic characterization of the target compound reinforces fundamental skills in 1H NMR, 13C NMR, and IR analysis and interpretation.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Feature):
The Microscale LaboratoryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
SynthesisCiting Articles
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This article has been cited by 7 ACS Journal articles (5 most recent appear below).
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- Received: August 03, 2009
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