Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage

Zhong-Zhen Zhou; Mingxin Liu; Leiyang Lv; Chao-Jun Li

doi:10.1002/anie.201711531

Silver(I)-Catalyzed Widely Applicable Aerobic 1,2-Diol Oxidative Cleavage

Angew Chem Int Ed Engl. 2018 Mar 1;57(10):2616-2620. doi: 10.1002/anie.201711531. Epub 2018 Feb 8.

Authors

Zhong-Zhen Zhou^{1

2}, Mingxin Liu¹, Leiyang Lv^{1

3}, Chao-Jun Li¹

Affiliations

¹ Department of Chemistry and FRQNT Center for Green Chemistry and Catalysis, McGill University, Montreal, QC, H3A 0B8, Canada.
² School of Pharmaceutical Sciences, Southern Medical University, No.1023 South Shatai Road, Guangzhou, 510515, China.
³ Department State Key Laboratory of Applied Organic Chemistry, Lanzhou University, 222 Tianshui Road, Lanzhou, Gansu, 730000, China.

PMID: 29336100
DOI: 10.1002/anie.201711531

Abstract

The oxidative cleavage of 1,2-diols is a fundamental organic transformation. The stoichiometric oxidants that are still predominantly used for such oxidative cleavage, such as H₅ IO₆ , Pb(OAc)₄ , and KMnO₄ , generate stoichiometric hazardous waste. Herein, we describe a widely applicable and highly selective silver(I)-catalyzed oxidative cleavage of 1,2-diols that consumes atmospheric oxygen as the sole oxidant, thus serving as a potentially greener alternative to the classical transformations.

Keywords: 1,2-diols; aerobic oxidative cleavage; carboxylic acids; oxidation; silver catalysis.

Publication types

Research Support, Non-U.S. Gov't