Download PDF
CC BY-NC-ND 4.0 · SynOpen 2022; 06(01): 19-30
DOI: 10.1055/s-0040-1719888
paper

Indium-Mediated Reformatsky Reaction of Iododifluoro Ketones with Aldehydes: Preparation of α,α-Difluoro-β-hydroxyketone Derivatives in Water

Zhongyuan Li
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Jinwen Huang  ∗
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
b   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai, P. R. of China
,
Zhuang Ni
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Ran Sun
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Hui Nie
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Hui Tang
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Lixing Song
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
,
Fanhong Wu∗
a   School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, P. R. of China
b   Shanghai Engineering Research Center of Green Fluoropharmaceutical Technology, Shanghai, P. R. of China
› Author AffiliationsWe are grateful for financial support from the National Natural Science Foundation of China (21672151 and 21472126).
› Further Information
   Permissions and Reprints All articles of this category


Abstract

Indium can efficiently mediate the Reformatsky reaction of iododifluoroacetylketones with aldehydes to afford the corresponding α,α-difluoro-β-hydroxyketones in high yield in pure water This reaction has excellent substrate suitability and functional group selectivity and provides an efficient approach for the synthesis of bioactive molecules containing the α,α-difluoro-β-hydroxyketone pharmacophore.

Key words

Indium - Reformatsky reaction - α-iodo-α,α-difluoroketone - α,α-difluoro-β-hydroxyketone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719888.
  • Supporting Information


Publication History

Received: 14 November 2021

Accepted after revision: 21 December 2021

Article published online:
31 January 2022

© 2022. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany