124318-70-3

Upstream product

• 66-71-7 1,10-Phenanthroline 
• 16932-45-9 1-bromo-2,6-dimethoxybenzene 
• 7089-68-1 2-chloro-[1,10]phenanthroline 
• 23112-96-1 (2,6-dimethoxyphenyl)boronic acid 
• 250665-25-9 C₁₀H₁₅BO₄ 
• 151-10-0 1,3-Dimethoxybenzene 

Downstream Products

• 124318-73-6 2,9-Bis(2',6'-dihydroxyphenyl)-1,10-phenanthroline 

Relevant academic research and scientific papers

A facile route to Aryl-substituted 1,10-phenanthrolines by means of Suzuki coupling reactions between substituted areneboronic acids and halogeno-1,10-phenanthrolines

Twelve new mono- or diaryl-substituted 1,10-phenanthrolines (17 and 18) have been synthesized. The key step is a Suzuki coupling reaction between the substituted areneboronic acids 6, 11, and 15 and the mono- and dihalo-1,10-phenanthrolines 16. The syntheses of bis-ortho-substituted boronic acids 6, 11, and 15 from substituted arenes 5 or substituted bromoarenes 10 and 14 by lithiation and subsequent treatment with trimethyl borate is described. Not only 2,9-diiodo- (16c) but also 2,9-dichloro-1,10-phenanthroline (16b) can be used with good yields (65-92%) in the described Suzuki coupling. For the syntheses of unsymmetrically substituted 1,10-phenanthrolines 18b, 18i, and 18j, the use of 2- chloro-9-iodo-1,10-phenanthroline is not necessary; two different bis-ortho-substituted arene rings can be introduced stepwise in 46 to 64% total yield. ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

Bimacrocyclic 1,10-Phenanthroline Cyclophanes

The addition of lithium aryls 3 to 1,10-phenanthroline (2), functionalization of the rearomatized bisadduct 8b to the tetraphenol 8d, and cyclization of 8d with two equivalents of an α,ω-ditosylate 9 led to a highly symmetrical, conformer-free bimacrocyclic 1,10-phenanthroline 10a in which the basic and coordinating region possesses a concave shielding.