Abstract

Trialkylsilyl triflates promote the direct nucleophilic reaction of “non-nucleophilic DBU and DBN” with methyl pheophorbide a ( 1) to give substituted chlorin e 6 amides 3 and 4, where the bicyclic bases have undergone ring opening. The reaction most likely results from coordination of trialkylsilyl triflates to the β-ketoester in 1, forming an ion-pair intermediate 6. The adduct 6 is so strongly electron-deficient that it can electrophilically attack the nonbonding nitrogen electron pairs in DBU and DBN.

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