Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones - The

Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones ... hydroxyl and amino moieties and displays chemoselective hydroboration of aldehydes ...
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Article Cite This: J. Org. Chem. 2018, 83, 69−74

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Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones Weifan Wang,† Xingchao Shen,† Fengyi Zhao,† Huan Jiang,† Weiwei Yao,‡ Sumod A. Pullarkat,§ Li Xu,† and Mengtao Ma*,† †

College of Science, Nanjing Forestry University, Nanjing 210037, People’s Republic of China College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, People’s Republic of China § Division of Chemistry & Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore ‡

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ABSTRACT: The well-defined heavy rare-earth ytterbium iodide complex 1 (L2YbI) has been successfully employed as an efficient catalyst for the hydroboration of a wide range of aldehydes and ketones with pinacolborane (HBpin) at room temperature. The protocol requires low catalyst loadings (0.1− 0.5 mol %) and proceeds rapidly (>99% conversion in