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Copper-Catalyzed Borylative Ring Closing C–C Coupling toward Spiro- and Dispiroheterocycles
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-02-23 00:00:00 , DOI: 10.1021/acscatal.8b00257
Jordi Royes 1 , Shaofei Ni 2 , Albert Farré 1 , Enrico La Cascia 1 , Jorge J. Carbó 1 , Ana B. Cuenca 1, 3 , Feliu Maseras 2 , Elena Fernández 1
Affiliation  

The synthesis of spiroheterocyclic structures with a pendant methylene boronate substituent has been accomplished to promote further functionalization. A Cu-catalyzed borylative ring closing C–C coupling of an alkenyl halide is the key step toward the synthesis of [m.n]-spirocycles (m,n = 3–5). Computational studies on the mechanism reproduced all the experimental trends and explain the enhanced reactivity of systems leading to strained smaller rings. The optimized protocol also gives access to dispirocycle scaffolds, fully characterized by X-ray diffraction.

中文翻译:

铜催化的螺环和双螺杂环的硼化环闭合CC连接

具有侧基亚甲基硼酸酯取代基的螺杂环结构的合成已经完成,以促进进一步的功能化。铜催化卤化烯基卤化物的C–C闭合是[ m]合成的关键步骤。n ]-螺环(mn = 3–5)。关于该机理的计算研究再现了所有实验趋势,并解释了导致较小的环应变的系统增强的反应性。经过优化的方案还可以访问双螺环支架,该支架具有X射线衍射的完全特征。
更新日期:2018-02-23
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