Title
Some Mercuration Reactions of Substituted Pyrroles
Document Type
Article
Publication Date
9-1-1989
Abstract
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
First Page
4801
Last Page
4807
Recommended Citation
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