A practically intriguing catalytic domino methodology has been developed for the synthesis of highly functionalized pyran and ethene-1,1,2-tricarbonitrile derivatives in a single-pot operation. The gem-dicyano olefins and the corresponding epoxide were taken as the reactive partners in the presence of a hydrogen bond donor (HBD)-catalyzed condition. The reaction was found to be highly efficient in terms of the formation of sequential C–C and O–C bonds along with an exceptional C_Sp²–C_Sp coupling step through a metal-free organocatalytic pathway. This strategy has been further utilized on ester-substituted epoxides, although the results differ from those with gem-dicyano epoxides. The process remains versatile and effective across a wide range of substrates. This catalytic protocol has been proven to be very generalized with varieties of substrate scope. A low catalyst loading, ambient reaction conditions, and satisfactory yields of all of the products are the vital features of this approach. Moreover, the overall atom-economic outcome along with the synergistic reactivity pattern between the activated epoxide and the malononitrile derivatives is also very significant to address the originality of this process. Spectroscopic analysis is utilized to validate the mechanistic interpretation.

中文翻译：

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氢键供体催化的 2,2-二取代环氧化物的一锅转化：功能化富腈衍生物的合成


已经开发了一种实用有趣的催化多米诺骨牌方法，用于在单罐操作中合成高度官能化的吡喃和乙烯-1,1,2-三碳酸腈衍生物。在氢键供体 （HBD） 催化条件下，将 gem-dicyano 烯烃和相应的环氧化物作为反应性伴侣。发现该反应在形成连续的 C-C 和 O-C 键以及通过无金属有机催化途径的特殊 C_Sp^2-C _Sp 偶联步骤方面非常有效。这种策略已进一步用于酯取代的环氧化物，尽管结果与 gem-dicyano 环氧化物的结果不同。该工艺在各种基材上仍然具有多功能性和有效性。这种催化方案已被证明在各种底物范围内非常普遍。低催化剂负载量、环境反应条件和令人满意的所有产物产率是这种方法的重要特征。此外，整体原子经济结果以及活化环氧化物和丙二腈衍生物之间的协同反应模式对于解决这一过程的独创性也非常重要。光谱分析用于验证机理解释。