Recent Progress in Non‐Catalytic C–H Functionalization of Heterocyclic N‐Oxides

• Published in: European journal of organic chemistry Vol. 2021; no. 3; pp. 357 - 373
• Main Authors: Kutasevich, Anton V., Perevalov, Valery P., Mityanov, Vitaly S.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 22.01.2021
• Subjects: 1,3‐Dipolar cycloaddition; Cine‐substitution; C‐H functionalization; Nitrogen heterocycles; N‐oxides; Oxides; Transition metals
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.202001115

Considerable attention holds on the chemistry and application of heterocyclic N‐oxides due to their advantages as building‐blocks in organic synthesis and importance in biomedical research. On the other hand, in recent years the development of selective methods for constructing C–C, C–N, C–P, C–S, and C–O bonds via direct C–H functionalization has become especially demand in organic synthesis. These circumstances determine the significance of this minireview, which present recent advances in the field of C–H functionalization of heterocyclic N‐oxides. Data on various type reactions which formal result is the replacement of a hydrogen atom in a heterocycle, with the exclusion of methods using heterogeneous and homogeneous catalysts based on transition metals, are summarized. Presented works for the last 15 years, since 2006. The present review demonstrates that the synthetic potential of heterocyclic N‐oxides performs it possible to successfully use them in the synthesis and modification of substances with high molecular complexity, including natural targets. Several effective catalyst‐free approaches for regioselective C–O, C–S, C–P, C–N, and C–C cross‐coupling, including Suzuki‐ and Heck‐like reactions, are especially noteworthy.