Wang, Xiaoshuang; Sun, Lei; Wang, Miaomiao; Maestri, Giovanni; Malacria, Max; Liu, Xiang; Wang, Yanlan; Wu, Lingang published an article in 2022. The article was titled 《C-I Selective Sonogashira and Heck Coupling Reactions Catalyzed by Aromatic Triangular Tri-palladium》, and you may find the article in European Journal of Organic Chemistry.Computed Properties of C6H4BrI The information in the text is summarized as follows:
Aromatic triangular tri-palladium cations, abbreviated as [Pd3]+, have shown interesting photoelec. properties, Lewis basic character, and excellent activities in catalytic hydrogenation. Herein, authors report the highly efficient and C-I selective Sonogashira and Heck coupling reactions catalyzed by these tri-palladium complexes. Benefiting from the moderate C-I bond association energy, these tri-palladiums presented exclusive reactivities to aryl iodides over the brominated aromatics in coupling reactions. In the Sonogashira pathway, good to excellent isolated yields (71-95%) were achieved. Gram-scale reaction reached 93% of yield with palladium loading as few as 0.06 mol %. Authors also explored the electronic and steric effects for Ph alkynes and aryl iodides including heteroaromatics like thiophene, pyridine, pyrazole, and pyrazine. Similarly, yields of 71-96% were obtained for palladium loading of 1.5 mol% through catalyzed Heck coupling of aryl iodides and alkenes. The HRMS monitoring revealed that [Pd3]+ maintained as whole entity during the catalytic process due to its robusness. In addition to this study using 1-Bromo-3-iodobenzene, there are many other studies that have used 1-Bromo-3-iodobenzene(cas: 591-18-4Computed Properties of C6H4BrI) was used in this study.
1-Bromo-3-iodobenzene(cas: 591-18-4) has been used in the preparation of 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.Computed Properties of C6H4BrI Further, it is involved in the preparation of oxygen-tethered 1,6-enynes.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com