10.1021/acs.joc.9b02992.s001 Yu Gao Yu Gao Zhihao Zhang Zhihao Zhang Zhenjiang Li Zhenjiang Li Tianfo Guo Tianfo Guo Yuejia Zhu Yuejia Zhu Zhiwei Yao Zhiwei Yao Bo Liu Bo Liu Yongqiang Li Yongqiang Li Kai Guo Kai Guo 4,5-Dioxo-imidazolinium Cation Activation of 1‑Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione American Chemical Society 2019 building blocks cyanoformamide group compatibility DCID modifiable dichloroimidazolidinediones reaction times 30 examples Dichloroimidazolidinedione Cyanoformamides dichloroimidazolidinedione-mediated chemistry 1- acyl -1-carbamoyl oximes activation alternative approach novel method accessing synthetically 2019-12-31 13:38:01 Journal contribution https://acs.figshare.com/articles/journal_contribution/4_5-Dioxo-imidazolinium_Cation_Activation_of_1_Acyl-1-carbamoyl_Oximes_Access_to_Cyanoformamides_Using_Dichloroimidazolidinedione/11482212 Cyanoformamides are prevalent as versatile building blocks for accessing synthetically useful intermediates and biologically active compounds. The development of a milder, simpler, and more efficient approach to cyanoformamides is nontrivial. Herein, we demonstrate the effectiveness of 4,5-dioxo-imidazolinium cation activation for transforming 1-acyl-1-carbamoyl oximes to cyanoformamides. By making use of the readily available and highly modifiable dichloroimidazolidinediones (DCIDs), this novel method of activation offers reactivity remarkably greater than that of other reported protocols, exhibits a high functional group compatibility with mild conditions, and could be scaled up easily. More than 30 examples are demonstrated with good to excellent yields in short reaction times. This research not only provides a mild and efficient alternative approach to assembling a portfolio of cyanoformamides but also extends the dichloroimidazolidinedione-mediated chemistry to encompass the C–C bond cleavage reaction.