Sam Yruegas

Expedient Synthesis of 1,2-Thiaborines by Means of Sulfur Insertion into Boroles.

The propensity of boroles to undergo ring expansion reactions has been exploited as a route to generate 1,2-thiaborines, molecules that can be viewed as hybrid inorganic/organic analogues of benzene. Computational studies as well as structural data indicate that the species reported here have a high degree of aromatic character.

Intermolecular insertion reactions of azides into 9-borafluorenes to generate 9,10-B,N-phenanthrenes

The reactions of 9-borafluorenes with organic azides result in either the insertion of the α-nitrogen and elimination of N2 or the insertion of the γ-nitrogen to generate the corresponding phenanthrene analogues with boron and nitrogen in the 9- and 10-positions, respectively.

Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis

We report herein an iron-catalyzed azidotrifluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo-radical instead of a carbocation species. Characterization of an active iron catalyst through X-ray crystallographic studies suggests that in situ generated, structurally novel iron-azide complexes promote the oxidant activation and selective azido-group transfer.

CCDC 1443361: Experimental Crystal Structure Determination

Related Article: Sam Yruegas, Kexuan Huang, David J. D. Wilson, Jason L. Dutton, Caleb D. Martin|2016|Dalton Trans.|45|9902|doi:10.1039/C6DT00052E