Divergent isoindolinone synthesis through palladium-catalyzed isocyanide bridging C-H activation was written by Zhang, Fulin;Zhao, Ruihua;Zhu, Lei;Yu, Yinghua;Liao, Saihu;Wang, Zhi-Xiang;Huang, Xueliang. And the article was included in Cell Reports Physical Science in 2022.Synthetic Route of C8H4BrF3O This article mentions the following:
An isocyanide-bridging C-H activation through the formation of a five-membered palladacycle was reported. As such, a proximal C-H bond in aldehyde moiety is activated selectively. The subsequent palladium shift and intramol. C=N bond insertion construct a valuable isoindolinone framework. Compared with conventional isocyanide-promoted C-H bond activation, both carbon and nitrogen atoms in isocyanide are engaged in new bond formations. Three types of isoindolinones I [R = t-Bu, cyclohexyl, Bn, etc.; R1 = H, CN; R2 = H, Bn, 2H-1,3-benzodioxol-5-ylmethyl, etc.; R3 = H, F, OMe, etc.; R4 = H, Cl, NH2, etc.; R5 = H, Me, OTs, etc.; -R4R5– = -OCH2O-; -R5R6– = -(CH)4-; R6 = H, OMe, etc.] can be obtained selectively by variations of the reaction conditions. Mechanistic studies shed light on the reaction pathways. The synthetic potential of current methodol. is demonstrated by providing concise routes to key intermediates of indoprofen, indobufen, aristolactams, lennoxamine, and falipamil. In the experiment, the researchers used many compounds, for example, 2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7Synthetic Route of C8H4BrF3O).
2-Bromo-4-(trifluoromethyl)benzaldehyde (cas: 85118-24-7) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. Commercially available organobromine pharmaceuticals include the vasodilator nicergoline, the sedative brotizolam, the anticancer agent pipobroman, and the antiseptic merbromin. Synthetic Route of C8H4BrF3O
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary