Pd-Catalyzed Cross Coupling Strategy for Functional Porphyrin Arrays.

Abstract

Porphyrin arrays are an important class of compounds to study interporphyrin electronic interactions that are crucial in determining the rates of energy transfer and electron transfer reactions. When the electronic interactions become stronger, porphyrin arrays exhibit significantly altered optical and electronic properties owing to large oscillator strength and flexible electronic nature of porphyrins. In addition, porphyrins accept various metal cation in their cavities and the interporphyrin interactions depend upon the coordinated metal. With these in the background, porphyrin arrays have been extensively explored as sensors, multielectron catalysts, photodynamic therapy reagents, artificial photosynthetic antenna, nonlinear optical materials, and so on. Here, we review the synthesis of porphyrin arrays by palladium-catalyzed cross-coupling reactions, which are quite effective to construct carbon–carbon bonds and carbon–nitrogen bonds in porphyrin substrates. Palladium-catalyzed cross coupling reactions employed so far are Suzuki–Miyaura coupling reaction, Sonogashira coupling reaction, Buchwald–Hartwig amination, Mizoroki–Heck reaction, Migita–Kosugi–Stille coupling reaction, and so on. In each case, the representative examples and synthetic advantages are discussed.