Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127, China.
State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin, 300071, China.
Angew Chem Int Ed Engl. 2017 Mar 1;56(10):2767-2771. doi: 10.1002/anie.201612127. Epub 2017 Jan 27.
A novel palladium(0)-catalyzed dearomatizing [2+2+1] spiroannulation of 1-bromo-2-naphthols with aryl iodides and alkynes was developed for the rapid assembly of spiro[indene-1,1'-naphthalen]-2'-ones. This three-component cascade reaction was realized through consecutive Catellani-type C-H activation, unsymmetrical biaryl coupling, alkyne migratory insertion, and arene dearomatization. The potential utility of our method is illustrated by the one-step construction of the polycyclic skeletons of dalesconols A and B from alkyne-tethered aryl iodides and 1-bromo-2-naphthol.
发展了一种新型钯(0)催化的 1-溴-2-萘酚与芳基碘化物和炔烃的去芳构化[2+2+1]螺环[茚并-1,1'-萘]并-2'-酮的 dearomatizing [2+2+1]螺环化反应。该三组分级联反应通过连续的 Catellani 型 C-H 活化、不对称联芳基偶联、炔烃迁移插入和芳环去芳构化来实现。我们的方法的潜在用途通过从炔烃键合的芳基碘化物和 1-溴-2-萘酚一步构建 dalesconols A 和 B 的多环骨架得到说明。
