Aromatic CH Borylation Catalyzed by Iridium/2,6‐Diisopropyl‐<i>N</i>‐(2‐pyridylmethylene)aniline Complex

Tsuyosi Tagata, Mayumi Nishida

doi:10.1002/adsc.200404179

Aromatic CH Borylation Catalyzed by Iridium/2,6‐Diisopropyl‐<i>N</i>‐(2‐pyridylmethylene)aniline Complex

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<jats:title>Abstract</jats:title><jats:p>The CH borylation of aromatic and heteroaromatic compounds, such as benzene, 1,3‐dichlorobenzene, 1,3‐bis(trifluoromethyl)benzene, 2,6‐dichloropyridine, indole, benzothiophene and benzofuran, by bis(pinacolato)diboron or pinacolborane was catalyzed by a 1/2 [IrCl(COD)]<jats:sub>2</jats:sub>‐2,6‐diisopropyl‐<jats:italic>N</jats:italic>‐(2‐pyridylmethylene)aniline complex. The isopropyl groups of the ligand are essential for obtaining the products in high yield. Octane was a suitable solvent for the reactions of the above compounds except for indole. In the case of indole, DME was better than octane and the yield tended to improve with a smaller amount of the catalyst.</jats:p>