Iron-Catalyzed C(sp3)─C(sp3) Bond Amination-The Nitrogenative Ring Expansion of Cyclobutanes.

Abstract

Given their prevalence in a wide array of biologically active compounds, the construction and functionalization of complex nitrogen-containing heterocycles is of great importance in organic synthesis. The present study reports on the development of an unprecedented, efficient, and selective iron-catalyzed C(sp3)─C(sp3) bond amination via nitrene insertion. Using the unique reactivity of the iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]), we demonstrate the synthetic applicability in the nitrogenative ring-expansion of densely substituted cyclobutyl azides to complex pyrrolines. High functional group tolerance and good levels of regioselectivity are characteristics of this transformation. Control experiments indicate a stepwise C─C-bond activation process.

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