An efficient intermolecular C(aryl)–S bond forming reaction catalyzed by BINAM–copper(II) complex

Organometallic Approaches to Carbon–Sulfur Bond Formation

“…The functional group diversity of the aryl iodide employed is similar to that reported by Buchwald, demonstrating the power of this ligand [35]. Pseudohalides, in particular tosylates, could be coupled using BINAM with a Cu(II) precatalyst, although the reaction is quite sensitive to electronic effects [50]. Lower catalyst loadings were achieved using bis(7-azaindolyl)methanes (2), which generate dinuclear complexes with bridging iodides and contained eight-membered chelate rings.…”

Copper and l -sodium ascorbate catalyzed hydroxylation and aryloxylation of aryl halides

“…1-Chloro-4-(4-methoxyphenoxy)benzene (3d). 23 19,156.13,149.75,129.51,127.32,120.80,118.73,114.94, 156.17, 149.59, 132.46, 120.87, 119.15, 114.95, 114.68, 55.62 d¼155.77, 155.26, 151.07, 131.25, 129.03, 126.92, 123.04, 119.28, 117.99, 114.76, 55.63, 16.19. 4.3.9. 1-(4-Methoxyphenoxy)-3-nitrobenzene (3i).…”

Diamine ligands in copper-catalyzed reactions

“…A range of different useful ligands have emerged including phenanthrolines, 3,16,17 α-amino acids, 4,12,18,19 1,3-diketones, 20,21 imines, 22,23 salicylamides 24 and others 6,25–39 as well as “ligand-free” systems. 40–45 A key advantage of diamine-based ligand systems for copper over some others that have been brought forward is the large scale access to the ethylenediamine and cyclohexanediamine backbones (it should be noted there have also been studies with BINAM 46–48 ) and the commercial availability of the ligands.…”