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Low-Temperature Formation of Functionalized Grignard Reagents from Direct Oxidative Addition of Active Magnesium to Aryl Bromides

Jun-sik Lee, Raffet Velarde-Ortiz, Albert Guijarro and Reuben D. Rieke*

*Department of Chemistry, University of NebraskaLincoln, Lincoln, Nebraska 68588-0304, USA

J.-s. Lee, R. Valerde-Ortiz, A. Guijarro, R. D. Rieke, J. Org. Chem., 2000, 65, 5428-5430.

DOI: 10.1021/jo000413i

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The use of activated Magnesium (Rieke Magnesium) enables the preparation of functionalized Grignard reagents at low temperatures. The Grignard reagents were reacted with several electrophiles such as benzaldehyde, benzoyl chloride, or allyl iodide. The reaction of benzoyl chloride yielded ketones with little or no addition to the carbonyl functionality due to the low temperature.

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Key Words

Grignard reaction, alcohols

ID: J42-Y2000