A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized
efficiently by a base-induced reaction of stannylated TosMIC with Michael acceptors. Stille cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been
achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo-coupling
reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from
stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.
Three different approaches are described for the generation of derivatives of 2,3-dimethyiene-2,3-dihydropyrrole 2, which are reactive intermediates in Diels-Alder cycloaddition reactions; one of the intramolecular cycloadditions provides a new tricyclo[3.2.1.0*~7]octane compound 8.
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