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Ytterbium-Catalyzed Hydroboration of Aldehydes and Ketones

Author:
Wang, Weifan, Shen, Xingchao, Zhao, Fengyi, Jiang, Huan, Yao, Weiwei, Pullarkat, Sumod A., Xu, Li, Ma, Mengtao
Source:
Journal of organic chemistry 2018 v.83 no.1 pp. 69-74
ISSN:
1520-6904
Subject:
aldehydes, ambient temperature, catalysts, chemical reactions, chemoselectivity, iodides, ketones, moieties, organic chemistry, protocols, ytterbium
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.
Agid:
6046606