Porphyrin macrocycles have been the subject of intense study in the last century because they are widely distributed in nature, usually as metal complexes of either iron or magnesium. As such, they serve as the prosthetic groups in a wide variety of primary metabolites, such as hemoglobins, myoglobins, cytochromes, catalases, peroxidases, chlorophylls, and bacteriochlorophylls; these compounds have multiple applications in materials science, biology and medicine. This article describes current methodology for preparation of simple, symmetrical model porphyrins, as well as more complex protocols for preparation of unsymmetrically substituted porphyrin macrocycles similar to those found in nature. The basic chemical reactivity of porphyrins and metalloporphyrin is also described, including electrophilic and nucleophilic reactions, oxidations, reductions, and metal-mediated cross-coupling reactions. Using the synthetic approaches and reactivity profiles presented, eventually almost any substituted porphyrin system can be prepared for applications in a variety of areas, including in catalysis, electron transport, model biological systems and therapeutics.

卟啉大环化合物在上个世纪一直是深入研究的主题，因为它们在自然界中广泛分布，通常作为铁或镁的金属配合物。因此，它们在多种初级代谢物中充当辅基，例如血红蛋白、肌红蛋白、细胞色素、过氧化氢酶、过氧化物酶、叶绿素和细菌叶绿素；这些化合物在材料科学、生物学和医学领域有多种应用。本文描述了目前制备简单、对称模型卟啉的方法，以及制备与自然界中发现的类似的不对称取代的卟啉大环化合物的更复杂的方案。还描述了卟啉和金属卟啉的基本化学反应性，包括亲电和亲核反应、氧化、还原和金属介导的交叉偶联反应。使用所提出的合成方法和反应性曲线，最终几乎可以制备任何取代的卟啉系统，用于各种领域的应用，包括催化、电子传输、模型生物系统和治疗学。