Ruthenium-Catalyzed Tandem Activation of C≡N and B−H Bonds under Dihydrogen: Synthesis of BN Heterocycles

Marion Beguerie (1) , Charly Faradji (1) , Laure Vendier (1) , Sylviane Sabo-Etienne (1) , Gilles Alcaraz (2)

1 LCC - Laboratoire de chimie de coordination
2 ISCR - Institut des Sciences Chimiques de Rennes

The incorporation of a nitrile function ortho to the B(sp2)HNiPr2 group to obtain cyano(aryl)boranes and subsequent ruthenium-catalyzed transformation of these cyano(aryl)boranes under a dihydrogen atmosphere (0.1 MPa) provided direct access to NH-containing 1H-2,1-benzazaboroles as BN analogues of indene under very mild conditions (i.e., room temperature). The BN heterocycle could be functionalized from the corresponding lithium amide either by N-elementation with various p-block (C, Si, P, B) electrophiles or by palladium-catalyzed N-arylation with aryl bromides thus to provide a new and powerful protocol for B−N bond decoration.

Keywords: homogeneous catalysis; hydrogenation; ruthenium; heterocycles; boranes

Domains: Chemical Sciences; Catalysis; Chemical Sciences; Organic chemistry

Marion Beguerie, Charly Faradji, Laure Vendier, Sylviane Sabo-Etienne, Gilles Alcaraz. Ruthenium-Catalyzed Tandem Activation of C≡N and B−H Bonds under Dihydrogen: Synthesis of BN Heterocycles. ChemCatChem, 2017, 9 (17), pp.3303-3306. ⟨10.1002/cctc.201700682⟩. ⟨hal-01596178⟩