Lewis base mediated halogenation/semipinacol rearrangement of diazo compounds: new access to α-halo-quaternary ketones

Abstract

A novel halogenation/semipinacol rearrangement of α-diazo alcohol catalyzed by Lewis base has been developed through a carbene-free mechanism. This semipinacol transposition, initiated by an electrophilic halogenation (X = Cl(+), Br(+), and I(+)) of diazo carbon event, furnished a convenient synthetic route for the efficient synthesis of α-halo-quaternary ketones under mild conditions.