Journal of Organic Chemistry 2014-02-07

Potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent: access to 2-nitroarenofurans.

Vitaly A Osyanin, Dmitry V Osipov, Maxim R Demidov, Yuri N Klimochkin

Index: J. Org. Chem. 79(3) , 1192-8, (2014)

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Abstract

The first example of the use of potassium trinitromethanide as a 1,1-ambiphilic synthon equivalent for the construction of a benzofuran moiety mediated by triethylamine has been developed. The method tolerates a variety of functional groups on the starting quaternary ammonium salt and has been successfully extended to polysubstituted benzofurans. Formation of an o-quinone methide intermediate is postulated as a key to the mechanism of this cascade process.