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

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