Kokel Anne, Schäfer Christian, Török Béla
Department of Chemistry, University of Massachusetts Boston, 100 Morissey Blvd., Boston, MA 02125, United States.
Curr Org Synth. 2019;16(4):615-649. doi: 10.2174/1570179416666190206141028.
Recent advances in the application of environmentally benign acid catalysts in organic synthesis are reviewed. The work includes three main parts; (i) description of environmentally benign acid catalysts, (ii) synthesis with heterogeneous and (iii) homogeneous catalysts. The first part provides a brief overview of acid catalysts, both solid acids (metal oxides, zeolites, clays, ion-exchange resins, metal-organic framework based catalysts) and those that are soluble in green solvents (water, alcohols) and at the same time could be regenerated after reactions (metal triflates, heteropoly acids, acidic organocatalysts etc.). The synthesis sections review a broad array of the most common and practical reactions such as Friedel-Crafts and related reactions (acylation, alkylations, hydroxyalkylations, halogenations, nitrations etc.), multicomponent reactions, rearrangements and ring transformations (cyclizations, ring opening). Both the heterogeneous and homogeneous catalytic synthesis parts include an overview of asymmetric acid catalysis with chiral Lewis and Brønsted acids. Although a broad array of catalytic processes are discussed, emphasis is placed on applications with commercially available catalysts as well as those of sustainable nature; thus individual examples are critically reviewed regarding their contribution to sustainable synthesis.
本文综述了环境友好型酸催化剂在有机合成中的应用进展。这项工作包括三个主要部分:(i)环境友好型酸催化剂的描述,(ii)使用多相催化剂的合成,以及(iii)使用均相催化剂的合成。第一部分简要概述了酸催化剂,包括固体酸(金属氧化物、沸石、粘土、离子交换树脂、基于金属有机框架的催化剂)以及那些可溶于绿色溶剂(水、醇)且反应后可再生的酸催化剂(金属三氟甲磺酸盐、杂多酸、酸性有机催化剂等)。合成部分综述了一系列最常见和实用的反应,如傅克反应及相关反应(酰化、烷基化、羟烷基化、卤化、硝化等)、多组分反应、重排和环转化反应(环化、开环)。多相催化合成和均相催化合成部分均包括对手性路易斯酸和布朗斯特酸的不对称酸催化的概述。尽管讨论了广泛的催化过程,但重点是市售催化剂以及具有可持续性质的催化剂的应用;因此,对各个实例对可持续合成的贡献进行了批判性综述。