216988-53-3Relevant articles and documents
An approach to 2,3-dihydropyrroles and β-iodopyrroles based on 5-endo-dig cyclisations
Knight, David W.,Redfern, Adele L.,Gilmore, Jeremy
, p. 622 - 628 (2007/10/03)
A representative series of homopropargylic sulfonamides 19 and 22b have been found to undergo smooth 5-endo-dig cyclisation upon exposure to excess iodine in acetonitrile containing potassium carbonate. The resulting 4-iodo-2,3-dihydropyrroles 23 readily react with two equivalents of DBU in DMF at 20°C to give the corresponding β-iodopyrroles 24 and 26 in excellent yields by the elimination of toluene-p-sulfinic acid. Use of less than two equivalents of base results in some loss of iodine. The iodo-2,3-dihydropyrroles 23 can be used in palladium-catalysed coupling reactions as shown by the efficient formation of the Sonogashira product 29 under mild conditions.