Recent Advancement of Ullmann Condensation Coupling Reaction in the Formation of Aryl-Oxygen (C-O) Bonding by Copper-Mediated Catalyst

Choong Jian Fui,Md Lutfor Rahman,Shaheen M Sarkar,Mohd Sani Sarjadi

doi:10.3390/catal10101103

Choong Jian Fui, Md Lutfor Rahman + Show 2 more

Open Access

https://doi.org/10.3390/catal10101103

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Journal: Catalysts	Publication Date: Sep 24, 2020
Citations: 20	License type: CC BY 4.0

Affiliation: Universiti of Malaysia Sabah, University of Limerick

Abstract

Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and synthetic pharmaceuticals but also widely found in many pesticides, polymers, and ligands. Copper catalyst has received great attention owing to the low toxicity and low cost. However, traditional Ullmann-type couplings suffer from limited substrate scopes and harsh reaction conditions. The introduction of homogeneous copper catalyst with presence of bidentate ligands over the past two decades has totally changed this situation as these ligands enable the reaction promoted in mild condition. The reaction scope has also been greatly expanded, rendering this copper-based cross-coupling attractive for both academia and industry. In this review, we will highlight the latest progress in the development of useful homogeneous copper catalyst with presence of ligand and heterogeneous copper catalyst in Ullmann type C-O cross-coupling reaction. Additionally, the application of Ullmann type C-O cross coupling reaction will be discussed.

Highlights

The transition metal-catalyzed chemical transformation of organic electrophiles, and organometallic reagents have turned up as an exceedingly robust synthetic tool
The evolution of transition metal catalysts have attained a stage of civilization that authorizes for an extensive scope of chemical bonds formation partners to be combined efficiently [1]
The evolution of chemicals through the transition-metal catalyzed reaction is an exciting era for the chemistry of palladium [4], ruthenium [5], platinum [6], etc., and has been significantly adopted by the industry

Summary

Introduction

The transition metal-catalyzed chemical transformation of organic electrophiles, and organometallic reagents have turned up as an exceedingly robust synthetic tool. The evolution of chemicals through the transition-metal catalyzed reaction is an exciting era for the chemistry of palladium [4], ruthenium [5], platinum [6], etc., and has been significantly adopted by the industry. The copper-mediated C-C, C-O, C-N, and C-S bond formation is a part of one oldest reactions, emphasizing the Ullmann cross-coupling reaction [9,10]. TTyyppiiccaall ccooppppeerr--mmeeddiiaatteedd UUllllmmaannnn ccoonnddeennssaattiioonn rreeaaccttiioonn aanndd pprreessuummppttiivvee mmeecchhaanniissmm To modernize this prominent and classical Ullmann reaction, it is essential to establish a novel composittiioonn andd morphoollooggyy off catalyysstt,, ssuuiittaabbllee ssoollvveennttss,, aanndd rreedduucciinngg aaggeennttss. OGsot lsdtabisle tmhetaml aonsdt esxtahbibleitsmmeatarvl ealonuds feexahtuibriets, such as assemblage of different types involving materials science, the deportment of its own particles, Catalysts 2020, 10, x FOR PEER REVIEW Catalysts 2020, 10, 1103.

AArryyll CC--OO BBoonndd FFoorrmmation Catalyzed by Copper Metal

Supported-Copper Nanoparticles Catalyst

Homogeneous Catalyst

Findings

Medicinal Chemistry