Tris(cyclopentadienyl)lanthanide Complexes as Catalysts for Hydroboration Reaction toward Aldehydes and Ketones

Sufang Chen, Dandan Yan, Mingqiang Xue*, Yubiao Hong, Yingming Yao* and Qi Shen*

*College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, People's Republic of China, Email: xuemingqiangsuda.edu.cn, yaoymsuda.edu.cn, qshensuda.edu.cn

S. Chen, D. Yan, M. Xue, Y. Hong, Y. Yao, Q. Shen, Org. Lett., 2017, 19, 3382-3385.

DOI: 10.1021/acs.orglett.7b01335

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Abstract

Homoleptic cyclopentadienyl lanthanide complexes are excellent catalysts for the hydroboration of various aldehydes and ketones with pinacolborane. These robust lanthanide catalysts exhibited high reactivity with low catalyst loadings under mild conditions, good functional group tolerability, and unique carbonyl-selectivity.

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Note

Hydrolysis: The hydroborated product was exposed to air, a spoon of silica gel was then added, and refluxed with CHCl₃ (3 mL) and H₂O (3 mL) for 24 h. The reaction mixture was diluted with water (6 mL) and extracted with CHCl₃ (6 mL × 3 times). The organic phases were combined, evaporated and purified by column chromatography over silica-gel (100-200 mesh) using ethyl acetate/hexane (1:10 or 1:20) mixture as eluent. The resulting alcohol was characterized by ¹H and ¹³C NMR.

Mingqiang Xue, April 10, 2018

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Key Words

reduction of carbonyl compounds, pinacolboran

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ID: J54-Y2017