Multifunctional Bacteriochlorins from Selective Palladium-Coupling Reactions

Nonsymmetrical, multifunctional bacteriochlorin derivatives possessing different substituents at the beta-pyrrolic positions have been prepared by stepwise, selective functionalization of 3,13-dibromo-5-methoxybacteriochlorin via palladium-coupling reactions. The new derivatives reported here include monovalent bioconjugatable bacteriochlorin, orthogonally protected bacteriochlorin amino acid, and push-pull bacteriochlorins. Taken together, this study provides a route to previously unavailable bacteriochlorin architectures for fundamental studies and diverse applications.