Lehnherr Dan, Alzola Joaquin M, Lobkovsky Emil B, Dichtel William R
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York, 14853-1301 (USA).
Department of Chemistry and Chemical Biology, X-ray Crystallography Laboratory, Cornell University, Ithaca, New York, 14853-1301 (USA).
Chemistry. 2015 Dec 7;21(50):18122-7. doi: 10.1002/chem.201503418. Epub 2015 Oct 30.
Independent control of halide substitution at six of the seven naphthalene positions of 2-arylnaphthalenes is achieved through the regioselective benzannulation of chloro-, bromo-, and iodoalkynes. The modularity of this approach is demonstrated through the preparation of 44 polyheterohalogenated naphthalene products, most of which are difficult to access through known naphthalene syntheses. The outstanding regioselectivity of the reaction is both predictable and proven unambiguously by single-crystal X-ray diffraction for many examples. This synthetic method enables the rapid preparation of complex aromatic systems poised for further derivatization using established cross-coupling methods. The power and versatility of this approach makes substituted naphthalenes highly attractive building blocks for new organic materials and diversity-oriented synthesis.
通过氯代、溴代和碘代炔烃的区域选择性苯并环化反应，实现了对2-芳基萘七个萘位中六个位置的卤代取代的独立控制。通过制备44种多杂卤代萘产物证明了该方法的模块化，其中大多数产物难以通过已知的萘合成方法获得。该反应出色的区域选择性对于许多实例而言都是可预测的，并且通过单晶X射线衍射得到了明确证实。这种合成方法能够快速制备出复杂的芳香体系，这些体系可使用成熟的交叉偶联方法进行进一步衍生化。这种方法的强大功能和通用性使得取代萘成为新型有机材料和多样化合成中极具吸引力的构建模块。
