Iridium‐Catalyzed C(sp<sup>3</sup>)−H Borylation Using Silyl‐Bipyridine Pincer Ligands

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  • Ryohei Kawazu
    Department of Molecular and Material Sciences Interdisciplinary Graduate School of Engineering Sciences Kyushu University 6-1 Kasugakoen Kasuga-shi Fukuoka 816-8580 Japan
  • Takeru Torigoe
    Institute for Materials Chemistry and Engineering Kyushu University 6-1 Kasugakoen, Kasuga-shi Fukuoka 816-8580 Japan
  • Yoichiro Kuninobu
    Institute for Materials Chemistry and Engineering Kyushu University 6-1 Kasugakoen, Kasuga-shi Fukuoka 816-8580 Japan

抄録

<jats:title>Abstract</jats:title><jats:p>New ligands for the iridium‐catalyzed C(sp<jats:sup>3</jats:sup>)−H borylation of aliphatic compounds were established. In sharp contrast to 6‐methyl‐2,2′‐bipyridine and 6‐isobutyl‐2,2′‐bipyridine, 2,2′‐bipyridine and 1,10‐phenanthroline derivatives bearing a hydrosilylmethyl group (which would give a thermally stable NNSi pincer complex) served as suitable ligands for the reaction. Among them, a phenanthroline‐based NNSi pincer ligand was shown to be an excellent ligand, and various aliphatic compounds were efficiently converted to the corresponding borylated products using the Ir/NNSi pincer catalyst system. The NNSi pincer ligand showed unique selectivity and enabled the iridium‐catalyzed C(sp<jats:sup>3</jats:sup>)−H borylation using pinacolborane [H−B(pin)] instead of B<jats:sub>2</jats:sub>(pin)<jats:sub>2</jats:sub>. The formation of an iridium complex bearing a quinoline‐based NNSi pincer ligand from [IrCl(cod)]<jats:sub>2</jats:sub> was observed, and the catalytic activity of the complex was demonstrated.</jats:p>

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