A Nonmetal Approach to a-Heterofunctionalized Carbonyl Derivatives by Formal Reductive X—H Insertion

摘要

Synthetic methods leading to the formation of α-heterofunc-tionalized carbonyl derivatives are valuable for the preparation of important molecular targets. Among the varied synthetic approaches to these compounds, the direct func-tionalization of an X—H bond by insertion of a carbene equivalent has proven expedient and versatile. In practice, the required carbene synthons may be accessed by metal-catalyzed decomposition of a-diazo compounds. Despite the utility of this approach, its appeal is tempered by the fact that only a modest number of diazo compounds are commercially available, a circumstance that is due in large part to hazards associated with preparation, isolation, and storage of these compounds. Consequently, alternative strategies for the direct X—H functionalization transformation that retain the power and simplicity of the diazo decomposition approach, but broaden access to starting materials, would be desirable.