Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

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Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01289F, Paper

Zhanhui Yang, Zhongpeng Zhu, Renshi Luo, Xiang Qiu, Ji-tian Liu, Jing-Kui Yang, Weiping Tang
A highly efficient iridium catalyst is developed for the chemoselective reduction of aldehydes to alcohols in water, using formic acid as a reductant.

From the journal:

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

Zhanhui Yang,^a^b Zhongpeng Zhu,^a^c Renshi Luo,^a^d Xiang Qiu,^a Ji-tian Liu,^a Jing-Kui Yang^c and Weiping Tang*^a^e

*Corresponding authors

^aSchool of Pharmacy, University of Wisconsin–Madison, Madison, USA
E-mail: weiping.tang@wisc.edu

^bFaculty of Science, Beijing University of Chemical Technology, Beijing, P. R. China

^cSchool of Chemistry and Chemical Engineering, University of Chinese Academy of Sciences, Beijing, P. R. China

^dSchool of Pharmacy, Gannan Medical University, Ganzhou, P. R. China

^eDepartment of Chemistry, University of Wisconsin–Madison, Madison, USA

Abstract

A water-soluble highly efficient iridium catalyst is developed for the chemoselective reduction of aldehydes to alcohols in water. The reduction uses formic acid as the traceless reducing agent and water as a solvent. It can be carried out in air without the need for inert atmosphere protection. The products can be purified by simple extraction without any column chromatography. The catalyst loading can be as low as 0.005 mol% and the turn-over frequency (TOF) is as high as 73800 mol mol⁻¹ h⁻¹. A wide variety of functional groups, such as electron-rich or deficient (hetero)arenes and alkenes, alkyloxy groups, halogens, phenols, ketones, esters, carboxylic acids, cyano, and nitro groups, are all well tolerated, indicating excellent chemoselectivity.