» Articles » PMID: 34123004

Synthesis of Oxalamides by Acceptorless Dehydrogenative Coupling of Ethylene Glycol and Amines and the Reverse Hydrogenation Catalyzed by Ruthenium

Overview
Journal Chem Sci
Specialty Chemistry
Date 2021 Jun 14
PMID 34123004
Citations 1
Authors
Affiliations
Soon will be listed here.
Abstract

A sustainable, new synthesis of oxalamides, by acceptorless dehydrogenative coupling of ethylene glycol with amines, generating H, homogeneously catalyzed by a ruthenium pincer complex, is presented. The reverse hydrogenation reaction is also accomplished using the same catalyst. A plausible reaction mechanism is proposed based on stoichiometric reactions, NMR studies, X-ray crystallography as well as observation of plausible intermediates.

Citing Articles

Acceptorless dehydrogenative synthesis of primary amides from alcohols and ammonia.

Luo J, Zhou Q, Montag M, Ben-David Y, Milstein D Chem Sci. 2022; 13(13):3894-3901.

PMID: 35432908 PMC: 8966752. DOI: 10.1039/d1sc07102e.

References
1.
Kothandaraman J, Kar S, Sen R, Goeppert A, Olah G, Prakash G . Efficient Reversible Hydrogen Carrier System Based on Amine Reforming of Methanol. J Am Chem Soc. 2017; 139(7):2549-2552. DOI: 10.1021/jacs.6b11637. View

2.
Chen Z, Jiang Y, Zhang L, Guo Y, Ma D . Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction. J Am Chem Soc. 2019; 141(8):3541-3549. DOI: 10.1021/jacs.8b12142. View

3.
Wang A, Zhang T . One-pot conversion of cellulose to ethylene glycol with multifunctional tungsten-based catalysts. Acc Chem Res. 2013; 46(7):1377-86. DOI: 10.1021/ar3002156. View

4.
Zeng H, Guan Z . Direct synthesis of polyamides via catalytic dehydrogenation of diols and diamines. J Am Chem Soc. 2011; 133(5):1159-61. PMC: 3033491. DOI: 10.1021/ja106958s. View

5.
Kumar A, Janes T, Espinosa-Jalapa N, Milstein D . Selective Hydrogenation of Cyclic Imides to Diols and Amines and Its Application in the Development of a Liquid Organic Hydrogen Carrier. J Am Chem Soc. 2018; 140(24):7453-7457. PMC: 6502447. DOI: 10.1021/jacs.8b04581. View