Acceleration of the Eschenmoser coupling reaction by sonication: efficient synthesis of enaminones

Naga Durgarao Koduri; Bethany Hileman; Justin D. Cox; Halee Scott; Phuong Hoang; Alexa Robbins; Kyle Bowers; Lemma Tsebaot; Kun Miao; Maria Castaneda; Michael Coffin; Guan Wei; Tim D. W. Claridge; Kenneth P. Roberts; Syed Raziullah Hussaini

doi:10.1039/C2RA22033D

Acceleration of the Eschenmoser coupling reaction by sonication: efficient synthesis of enaminones†

Naga Durgarao Koduri,^a Bethany Hileman,^a Justin D. Cox,^a Halee Scott,^a Phuong Hoang,^a Alexa Robbins,^a Kyle Bowers,^a Lemma Tsebaot,^a Kun Miao,^a Maria Castaneda,^a Michael Coffin,^a Guan Wei,^a Tim D. W. Claridge,^b Kenneth P. Roberts^a and Syed Raziullah Hussaini*^a

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^a Department of Chemistry and Biochemistry, The University of Tulsa, Keplinger Hall, 800 South Tucker Drive, Tulsa, Oklahoma 74104, United States
E-mail: syed-hussaini@utulsa.edu
Fax: +1-918-631-3404
Tel: +1- 918-631-3520

^b Department of Chemistry, University of Oxford, 12 Mansfield Road, Oxford, United Kingdom

Abstract

Enaminones are commonly prepared by the Eschenmoser coupling reaction. The duration of the reaction is often long. Here, we describe how sonication can accelerate this reaction. The reaction conditions provide an efficient method for the coupling of primary, secondary and tertiary thioamides with α-bromocarbonyl compounds.

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Acceleration of the Eschenmoser coupling reaction by sonication: efficient synthesis of enaminones†

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Acceleration of the Eschenmoser coupling reaction by sonication: efficient synthesis of enaminones

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