89981-62-4Relevant articles and documents
Regiodivergent halogenation of vinylogous esters: One-pot, transition-metal-free access to differentiated haloresorcinols
Chen, Xiaohong,Martinez, Jenny S.,Mohr, Justin T.
, p. 378 - 381 (2015)
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.
Practical regioselective halogenation of vinylogous esters: Synthesis of differentiated mono-haloresorcinols and polyhalogenated resorcinols
Chen, Xiaohong,Liu, Xiaoguang,Martinez, Jenny S.,Mohr, Justin T.
, p. 3653 - 3665 (2016/06/06)
A practical and efficient method for the direct, regioselective conversion of vinylogous esters to haloresorcinols is reported. Control of the reaction conditions enables synthesis of either the 4- or 6-haloresorcinol isomers from a common precursor with excellent regiocontrol and high yield. The generality and functional group tolerance of this novel protocol is demonstrated. The utility of this methodology to access polyhaloresorcinols is also reported. These methods create useful functionalized building blocks for further synthetic applications.
