Synthesis of Imidazoles through the Copper-Catalyzed Cross-Cycloaddition between Two Different Isocyanides

• Published in: Journal of the American Chemical Society Vol. 128; no. 33; pp. 10662 - 10663
• Main Authors: Kanazawa, Chikashi, Kamijo, Shin, Yamamoto, Yoshinori
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 23.08.2006; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Multidisciplinary; Copper - chemistry; Cyanides - chemistry; Exact sciences and technology; General and physical chemistry; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Imidazoles - chemical synthesis; Molecular Structure; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; ISOCYANOACETATE; CARBONYL-COMPOUNDS; ASYMMETRIC ALDOL REACTION; ALDEHYDES; PYRROLES; COMPLEX CATALYSTS; Imidazole derivatives; Cycloaddition; Catalytic reaction; Copper ion; Nitrogen heterocycle; Chemical synthesis; Isocyanide
• ISSN: 0002-7863; 1520-5126
• DOI: 10.1021/ja0617439

The copper-catalyzed reaction between two different isocyanides produces the corresponding heteroaromatization products, imidazoles, in good yields. The reaction proceeds most probably through the activation of the sp3 C−H bond in the isocyanides by a copper catalyst, followed by a [3 + 2] cycloaddition between the cuprioisocyanide intermediates and arylisocyanides.