Iron-Catalyzed C-H Borylation of Arenes.

Thomas Dombray (1) , C. Gunnar Werncke (2, 3) , Shi Jiang , Mary Grellier (2, 3) , Laure Vendier (2) , Sébastien Bontemps (2) , Jean-Baptiste Sortais (1) , Sylviane Sabo-Etienne (2) , Christophe Darcel (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCC - Laboratoire de chimie de coordination
3 UT3 - Université Toulouse III - Paul Sabatier

Well-defined iron bis(diphosphine) complexes are active catalysts for the dehydrogenative C-H borylation of aromatic and heteroaromatic derivatives with pinacolborane. The corresponding borylated compounds were isolated in moderate to good yields (25-73%) with a 5 mol% catalyst loading under UV irradiation (350 nm) at room temperature. Stoichiometric reactivity studies and isolation of an original trans-hydrido(boryl)iron complex, Fe(H)(Bpin)(dmpe)2, allowed us to propose a mechanism showing the role of some key catalytic species.

Keywords: Iron; Hydrocarbons; Borylation; Catalysts; Irradiation

Domains: Chemical Sciences

Thomas Dombray, C. Gunnar Werncke, Shi Jiang, Mary Grellier, Laure Vendier, et al.. Iron-Catalyzed C-H Borylation of Arenes.. Journal of the American Chemical Society, 2015, 137 (12), pp.4062-4065. ⟨10.1021/jacs.5b00895⟩. ⟨hal-01153417⟩