Some Mercuration Reactions of Substituted Pyrroles
Mercuration of N-unsubstituted pyrroles with mercury(II) acetate results in immediate precipitation of the N-mercurated derivative, which is insoluble in virtually all organic solvents. If the pyrrole N atom is protected (e.g. with Me, CH2OCH2Ph, or CO2t-Bu) then mercuration takes place efficiently at unsubstituted pyrrole carbons. Subsequent palladium/olefin (Heck-type) reactions afford the corresponding pyrrole acrylate when, for example, the olefin is methyl acrylate; deprotection (when the N-substituent is CH2OCH2Ph or CO2t-Bu) then affords the required carbon-substituted pyrrole. Attempts to deprotect the N-methylpyrroles were unsuccessful. © 1989, American Chemical Society. All rights reserved.
Publication Source (Journal or Book title)
Journal of Organic Chemistry
Ganske, J., Pandev, R., Postich, M., Snow, K., & Smith, K. (1989). Some Mercuration Reactions of Substituted Pyrroles. Journal of Organic Chemistry, 54 (20), 4801-4807. https://doi.org/10.1021/jo00281a020