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. 2015 Jan 16;17(2):378-81.
doi: 10.1021/ol503561x. Epub 2015 Jan 7.

Regiodivergent halogenation of vinylogous esters: one-pot, transition-metal-free access to differentiated haloresorcinols

Xiaohong Chen  1 , Jenny S Martinez, Justin T Mohr
Affiliations

Regiodivergent halogenation of vinylogous esters: one-pot, transition-metal-free access to differentiated haloresorcinols

Xiaohong Chen et al. Org Lett. .

Abstract

We report an efficient method for the regiodivergent synthesis of halogenated resorcinol derivatives using readily available vinylogous esters and sulfonyl halide halogen donors. Either the 4- or 6-haloresorcinol isomer is accessible from a common precursor. In contrast to conventional oxidants for arene halogenation, mild sulfonyl halides allow broad functional group compatibility. The strategy inherently differentiates the two resorcinol oxygen atoms and enhances the potential for complex molecule synthesis.

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