Synthesis of 2,4-Bis(aryloxy)-1,5-diarylpentane-1,5-diones by Base-Mediated Tandem Reaction

Abstract

A new, practical, base-mediated method has been developed for the synthesis of 2,4-bis(aryloxy)-1,5-diarylpentane-1,5-diones by a tandem α-methylenation–Michael reaction through activation of two C–Cl bonds. This method permits the use of dichloromethane instead of dibromomethane as a source of one carbon atom for the α-methylenation reaction. The products are useful in syntheses of polysubstituted pyridines and methylenebisbenzofurans.

Key words

tandem reactions - ketones - Michael additions

• Reference

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• 9 The configuration of products 2 was unambiguously assigned by means of an X-ray single-crystal diffraction analysis of product 2k. See the Supporting Information for detailed data.