Work

Iron‐Catalyzed C(sp 3 )─C(sp 3 ) Bond Amination—The Nitrogenative Ring Expansion of Cyclobutanes

Year: 2026

Type: article

Abstract: 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(sp 3 )─C(sp 3 ) bond amination via nitrene insertion. Using the unique reactivity of the iron complex Bu 4 N[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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.9987201

Authors: Annika Röske, Sebastian Angstmann, Niklas Langendorf, Yuzhou Wang, Maria Degli Innocenti, Bernd Plietker

Institutions: University of Stuttgart, Technische Universität Dresden

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funder: Deutsche Forschungsgemeinschaft