Synthesis of 1-Formyldipyrromethanes
- 15 April 2006
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (11) , 4328-4331
- https://doi.org/10.1021/jo060119b
Abstract
1-Formyldipyrromethanes are versatile precursors to porphyrins and chlorins. Two methods of synthesis of 1-formyldipyrromethanes have been investigated: (1) Vilsmeier formylation followed by selective removal of the unwanted 1,9-diformyldipyrromethane by dialkyltin complexation and (2) reaction with mesitylmagnesium bromide (MesMgBr) followed by formylation with phenyl formate. The two approaches are complementary (acidic versus basic conditions; statistical versus selective formylation). The latter was found to be more efficient for the preparation of 1-formyldipyrromethanes.Keywords
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