Quiclet-Sire Béatrice, Zard Samir Z
Laboratoire de Synthèse Organique UMR 7652, Ecole Polytechnique, 91128 Palaiseau, France.
Org Biomol Chem. 2023 Feb 1;21(5):910-924. doi: 10.1039/d2ob02159e.
The present account summarises routes to tetralones, tetralines, and naphthalenes based on the chemistry of xanthates developed in the authors' laboratory. The degenerative reversible transfer of xanthates allows radical addition even to unactivated, electronically unbiased alkenes, and tolerates a broad range of functional groups, in particular common polar groups such as esters, ketones, nitriles, amides, carbamates, . Xanthates also allow radical ring closures onto aromatic rings. This feature, in combination with the intermolecular addition to alkenes, can be used to construct tetralones and tetralines. With the appropriate appendages, the former can be converted into napthalenes with a variety of substitution patterns. This translates into a convergent approach to a vast array of building blocks of interest to the pharmaceutical and agrochemical industries, and to material sciences.
本报告总结了基于作者实验室开发的黄原酸酯化学合成四氢萘酮、四氢萘和萘的方法。黄原酸酯的退化可逆转移允许自由基加成到未活化的、电子无偏向的烯烃上,并且能耐受多种官能团,特别是常见的极性基团,如酯基、酮基、腈基、酰胺基、氨基甲酸酯基等。黄原酸酯还能使自由基环合到芳环上。这一特性与烯烃的分子间加成相结合,可用于构建四氢萘酮和四氢萘。通过适当的附属基团,前者可转化为具有各种取代模式的萘。这转化为一种收敛的方法,可用于合成制药、农用化学品行业以及材料科学领域大量感兴趣的结构单元。