L-Proline catalyzed reaction of N-confused porphyrin and active methylene compounds.

TitleL-Proline catalyzed reaction of N-confused porphyrin and active methylene compounds.
Publication TypeJournal Article
Year of Publication2013
AuthorsLiu B, Li X, Zhang J, Chmielewski PJ
JournalOrganic & biomolecular chemistry
Volume11
Issue29
Pagination4831-9
Date Published2013 Aug 7
Abstract

Active methylene compounds such as acetone, butanone, cyclopentanone, nitromethane, malononitrile, ethyl 2-cyanoacetate, diethyl malonate, and ethyl acetylacetate react with the C3 position of N-confused porphyrin in the presence of L-proline in refluxing THF-EtOH affording a variety of N-confused porphyrin derivatives in moderate yield. L-Proline catalyzes the reaction facilitating the formation of the carbanion derived from an active methylene compound simultaneously delivering protons to the N-confused porphyrin. Both processes are key factors of this reaction.

DOI10.1038/ncomms3076
Alternate JournalOrg. Biomol. Chem.