4.8 Article

meta-Selective C-H Borylation of Benzamides and Pyridines by an Iridium-Lewis Acid Bifunctional Catalyst

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 19, 页码 7972-7979

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AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b03138

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  1. JST CREST program [JPMJCR14L3]
  2. JSPS KAKENHI [JP15H05799]

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We report herein the iridium-catalyzed meta-selective C-H borylation of benzamides by using a newly designed 2,2'-bipyridine (bpy) ligand bearing an alkylaluminum biphenoxide moiety. We also demonstrate the iridium-catalyzed C3-selective C-H borylation of pyridine with a 1,10-phenanthroline (Phen) ligand bearing an alkylborane moiety. It is proposed that the Lewis acid-base interaction between the Lewis acid moiety and the aminocarbonyl group or the sp(2)-hybridized nitrogen atom accelerates the reaction and controls the site-selectivity.

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