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

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:

Green Chemistry

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

Zhanhui Yang,ab  Zhongpeng Zhu,ac  Renshi Luo,ad  Xiang Qiu,a  Ji-tian Liu,a  Jing-Kui Yangc  and Weiping Tang*ae 

*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.

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC01289F?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

4-Methoxybenzyl alcohol (2a)2 . Yellowish oil. Yield: 273 mg, 99%.

1H NMR (400 MHz, CDCl3) δ 7.23 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 8.7 Hz, 2H), 4.52 (s, 2H), 3.76 (s, 3H).

13C NMR (101 MHz, CDCl3) δ 159.07, 133.23, 128.63, 113.89, 64.73, 55.30, 55.26.

Zhanhui Yang

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

School of Pharmacy
UNIVERSITY OF WISCONSIN - MADISON

Beijing University of Chemical... , Beijing

Organic Chemistry, Green Chemistry, Catalysis

PhD student

Beijing University of Chemical Technology

Organic Chemistry

Beijing, China

School of Pharmacy, University of Wisconsin–Madison, Madison, USA

4-Methoxybenzyl alcohol

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