Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

Abstract

The efficient copper-mediated oxidative C–H alkynylation of benzhydrazides was accomplished with terminal alkynes. Thus, a heteroaromatic removable N-2-pyridylhydrazide allowed for domino C–H/N–H functionalization. The approach featured remarkable functional group compatibility and ample substrate scope. Thereby, highly functionalized aromatic and heteroaromatic isoindolin-1-ones were accessed with high efficacy with rate-limiting C–H cleavage.

Earth-abundant 3d transition metals on the rise in catalysis

“…Directed C-H activations have been developed as increasingly amenable tools for proximity-induced C-H functionalizations. In this thematic issue, strategies are presented that guarantee position-selectivity in copper-mediated isoindolin-1-one synthesis [12] as well as in copper-catalyzed aminations of ferrocenes [13]. The exploitation of the innate reactivity of organic molecules can allow for indirected C-H transformations and herein, homolytic C-H cleavages are described for transformative manganese-catalyzed brominations of tertiary C-H bonds [14].…”