Journal of Catalysis ( IF 7.3 ) Pub Date : 2020-06-12 , DOI: 10.1016/j.jcat.2020.06.002 Amparo Luna , Fernando Herrera , Sheila Higuera , Alejandro Murillo , Israel Fernández , Pedro Almendros
Supported silver nitrate in silica gel has been demonstrated as an excellent heterogeneous catalytic system for the selective hydroarylation of indole-tethered allenes, with a selectivity reversal in comparison with homogeneous gold catalysis. In this way, the controlled preparation of 1,2-disubstituted-9H-carbazoles, 1,2-disubstituted-4,9-dihydro-1H-carbazoles, and 2,4-disubstituted-spiro[cyclopentane-1,3′-indol]-3-enes has been accomplished. Control experiments supported by Density Functional Theory calculations strongly suggest that indole-tethered allenes react through a 5-endo-dig-carbometallation/rearrangement sequence, which contrasts to the previously reported 6-endo-dig-carbometallation pathway promoted by [Au(I)]-catalysts in related systems.
中文翻译:
AgNO 3 ·SiO 2:利用多相催化可持续实现烯丙基-吲哚可持续加氢官能化的便捷AgNPs来源
硅胶中负载的硝酸银已被证明是一种出色的非均相催化体系,可用于吲哚系链的烯的选择性加氢芳基化,与均相金催化相比,其选择性可逆。这样,受控制备了1,2-二取代的9 H-咔唑,1,2-二取代的4,9-二氢-1 H-咔唑和2,4-二取代的螺[环戊烷-1,3 '-吲哚] -3-烯已完成。通过密度泛函理论计算支持的控制实验强烈表明,吲哚系留丙二烯通过5-反应内切-挖-carbometallation /重排顺序,对比于先前报道的6-内-挖相关系统中[Au(I)]-催化剂促进的碳-碳金属化途径。