Organoiodine-mediated dehydrogenative N–N coupling of aryl alkoxycarbamates

• Published in: Tetrahedron Vol. 147; pp. 133659 - 133664
• Main Authors: Liu, Ao, Cao, Chenhui, He, Jiayu, Zhao, Zhenze, Zhang, Chaozhi, Zhang, Xuan, Sun, Jinwei
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 30.10.2023; Elsevier
• Subjects: Aryl alkoxycarbamates; Chemistry; Chemistry, Organic; cross-coupling reactions; dehydrogenation; dimerization; Hypervalent iodine; iodobenzenes; N-N coupling; Oxidation; Phenylamide derivatives; Physical Sciences; Science & Technology; N-N coupling; Aryl alkoxycarbamates; Oxidation; Hypervalent iodine; Phenylamide derivatives; N -N coupling; AROMATIC AZO-COMPOUNDS; AMINES; ANILINES; HYDRAZINES
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2023.133659

An environmentally benign and efficient approach has been developed for the construction of corresponding N–N coupled dialkoxyhydrazines in good yields (up to 91%) via phenyliodine diacetate (PIDA) mediated oxidative dimerization of alkoxycarbamates. The advantages of this transformations are mild conditions, functional-group tolerance and operationally simple. Notably, the cross-coupling of two different aryl alkoxycarbamates is also demonstrated, which provides a straightforward method to structurally complex N–N molecules. An organoiodine-mediated N–N cross-coupling of two aryl alkoxycarbamates has been demonstrated, which provides a straightforward method to structurally complex N–N molecules. [Display omitted]