Sulfonato–Cu(salen) Complex CatalyzedN‐Arylation of Aliphatic Amines with Aryl Halides in Water

Abstract

A water-soluble sulfonato-Cu(salen) complex catalyzed procedure for the N-arylation of simple aliphatic amines, amino alcohols and amino acids in pure water have been developed. A variety of substituted aryl iodides, bromides and

Development of a Method for the N-Arylation of Amino Acid Esters with Aryl Triflates

“… 8 Other Cu-catalyzed methods employ harsh reaction conditions that likely result in racemization of the amino acid. 9 Comparatively little work has been done on the development of Pd-catalyzed N -arylation methods. 4 , 10 The reported conditions suffer from limited substrate scope, and significant racemization is observed for a majority of amino acids examined as substrates.…”

Salen-Cu(II) Complex Catalyzed <i>N</i>-Arylation of Imidazoles under Mild Conditions

“…The breakthroughs in this area, which were achieved by two research groups of Buchwald [11,12] and Taillefer, [13] respectively, have typically been driven by the implementation of new class of ligands and only catalytic amounts of copper metal under mild conditions. Following these pioneering works, several classes of mono-, bidentate, and polydentate chelators have thereby been developed to expedite the reaction rates and substantially lower the reaction temperature of Cu-based C-N coupling reaction [14][15][16][17][18][19][20][21][22][23][24][25][26][27]. In spite of the significant progress made in the aforementioned transformation, more efficient, air stable and cheaper ligands or metal-complexes for facilitating these coupling reactions under relatively milder conditions are still in demand.…”

μ-Hydroxyl trinuclear copper(ii) clusters: reactivity and unusual formation in the three-component synthesis of 1,2,3-triazoles in aqueous media

“…Copper salens derived from 1,2-diamines (denoted as salen, N,N-ethylenebis(salicylimine), in this work) have been used as catalysts in various reactions such as oxidations, 6 aldol reactions, 7 C-N couplings, 8 alkynylation couplings 9 and enantioselective separations as a helical framework. 10 The salen ligands are usually assumed to have a planar coordination mode in the reactive metal-salen intermediate.…”

“…10 The salen ligands are usually assumed to have a planar coordination mode in the reactive metal-salen intermediate. Although copper salens exhibit excellent catalytic reactivity, 7,8,12 in aqueous media the CvN bond in the copper salen tends to hydrolyse, 11 and therefore the real catalytic species still needs to be explored. In this work, we started by using copper salens as the catalyst in the three-component (sodium azide, epoxide, and non-activated terminal alkyne) 1,3-Huisgen cycloaddition in water.…”