Kinetic Selectivity in the N-Alkylation of 2-Pyridyl Porphyrins: A Facile Approach to the ααββ Scaffold

A Datta, SM Quintavalla, JT Groves

Index: Datta, Ankona; Quintavalla, Suzanne M.; Groves, John T. Journal of Organic Chemistry, 2007 , vol. 72, # 5 p. 1818 - 1821

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Citation Number: 6

Abstract

meso-Tetrakis (2-pyridyl)-porphyrin (2-PyP) was tetra-N-alkylated with three different α- bromoacetamides to generate a series of water-soluble N-alkylpyridinium porphyrins (1-3). The product mixtures showed a marked preference for the formation of the ααββ atropisomer. With α-bromo-Nn-butylacetamide, the corresponding ααββ 2-tetrakis (Nn- butylacetamido)-pyridyl porphyrin (2-TnBuPyP, 3) was obtained in 69% isolated yield in a ...