Nucleophilic ortho-allylation of pyrroles and pyrazoles: an accelerated Pummerer/thio-Claisen rearrangement sequence.

ABSTRACT: Arylsulfinyl groups direct the metal-free, regiospecific, nucleophilic ortho-allylation of pyrroles and pyrazoles. Mechanistic studies support the intermediacy of allylsulfonium salts that undergo facile thio-Claisen rearrangement onto the heterocyclic ring, giving products of coupling. The strategy has been adapted to allow regiospecific propargylation of the heterocyclic substrates.

SUBMITTER: Eberhart AJ 

PROVIDER: S-EPMC3819180 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature