Sustainable Aerobic Allylic C-H Bond Oxidation with Heterogeneous Iron Catalyst.

J Am Chem Soc

Key Laboratory of Material Chemistry for Energy Conversion and Storage (Ministry of Education), Hubei Key Laboratory of Material Chemistry and Service Failure, School of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, 1037 Luoyu Road, Wuhan 430074, China.

Published: January 2024

Emerging techniques are revolutionizing the realm of chemical synthesis by introducing new avenues for C-H bond functionalization, which have been exploited for the synthesis of pharmaceuticals, natural compounds, and functional materials. Allylic C-H bond oxidation of alkenes serves as possibly the most employed C-H bond functionalization reaction. However, sustainable and selective approaches remain scarce, and the majority of the existing conditions still hinge on hazardous oxidants or costly metal catalysts. In this context, we introduce a heterogeneous iron catalyst that addresses the above-mentioned concerns by showcasing the aerobic oxidation of steroids, terpenes, and simple olefins to the corresponding enone products. This novel method provides a powerful tool for the arsenal of allylic C-H bond oxidation while minimizing the environmental concerns.

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http://dx.doi.org/10.1021/jacs.3c12688DOI Listing

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