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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, Mengtao Ma

J Org Chem. 2018 Jan 5;83(1):69-74.

PMID: 29181979

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 <10 min). Additionally, catalyst 1 shows a good functional group tolerance even toward the hydroxyl and amino moieties and displays chemoselective hydroboration of aldehydes over ketones under mild conditions.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP7440644 Ytterbium Ytterbium 7440-64-4 Price
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