Ceric ammonium nitrate (CAN) enabled concerted nitration/ureation of carbodiimides to synthesize o-nitroaryl ureas. Issue 20 (23rd August 2021)

• Record Type: Journal Article
• Authors: Wang, Shilong; Xie, Xiangqi; Zhao, Xingchen; Liu, Jixin; Zhao, Ziling; Chen, Jinchun; Li, Jiazhu; Sun, Kai; Zhang, Zhen
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 20(2021)
• Page Start: 5771
• Page End: 5776
• Publication Date: 2021-08-23
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00943e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A simple and facile strategy to construct o -nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) with high functional group compatibility via concerted nitration/ureation has been described. Abstract : A simple and facile strategy to construct o -nitroaryl urea employing carbodiimides and ceric ammonium nitrate (CAN) has been developed. This protocol achieves the installation of two functional groups in one step with high functional group compatibility. Control experiments show that the reaction mechanism involves an intriguingly concerted nitration/ureation process enabled by CAN, and is distinctive from conventional electrophilic nitrification. The oxygen atom of urea probably originates from the nitrate ions provided by CAN. The late-stage derivatization and gram-scale synthesis reveal the promising utility of this methodology.