211742-03-9Relevant academic research and scientific papers
A Direct Synthesis of 2-(Trimethylstannyl)pyrroles from Michael Acceptors and Stannylated Tosylmethyl Isocyanide
Dijkstra, Harm P.,Ten Have, Ronald,Van Leusen, Albert M.
, p. 5332 - 5338 (1998)
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.
