Studies on Elimination Pathways of β-Halovinyl Ketones Leading to Allenyl and Propargyl Ketones and Furans under the Action of Mild Bases

Hun Young Kim, Jian-Yuan Li and Kyungsoo Oh*

*Department of Chemistry and Chemical Biology, Indiana University-Purdue University Indianapolis (IUPUI), Indianapolis, Indiana 46202, United States, Email: ohkiupui.edu

H. Y. Kim, J.-Y. Li, K. Oh, J. Org. Chem., 2012, 77, 11132-11145.

DOI: 10.1021/jo302253c

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Abstract

The elimination pathway of stereochemically defined β-halovinyl ketones has been investigated using a mild base, NEt₃, leading to the formation of allenyl ketones and propargyl ketones. In the presence of CuCl as a catalyst, the elimination reaction of β-chlorovinyl ketones enables a one-pot synthesis of 2,5-disubstituted furans.

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Key Words

Furans

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ID: J42-Y2012-3860