Silver(i)-promoted C5–H phosphonation of 8-aminoquinoline amides with H-phosphonates

Abstract

An efficient protocol for silver(i)-promoted C5–H phosphonation of 8-aminoquinoline amides with dialkyl H-phosphonates was developed.

Visible-Light-Promoted Transition-Metal-Free Phosphinylation of Heteroaryl Halides in the Presence of Potassium tert-Butoxide

“…Phosphorus-containing heteroaromatic molecules are an important class of compounds that find useful applications in synthetic transformations, medicinal chemistry, and photoelectric materials, and as useful ligands for transition metal catalysis . Although great effort has been devoted to the development of new and efficient strategies for C–P bond formation in recent decades, the synthesis of heteroaryl phosphines still meets with challenge owing to the effect of coordination of heteroatom to metal ion, which can suppress catalytic processes. − Traditionally, heteroaryl phosphines are prepared by nucleophilic substitution reaction of heteroaryl-metal unit and phosphine chlorides. At present, for the phosphonation of C­(sp 2 )–H bonds, a number of catalytic systems based on palladium, copper, and silver have been developed by several groups .…”

“…Although great effort has been devoted to the development of new and efficient strategies for C–P bond formation in recent decades, the synthesis of heteroaryl phosphines still meets with challenge owing to the effect of coordination of heteroatom to metal ion, which can suppress catalytic processes. − Traditionally, heteroaryl phosphines are prepared by nucleophilic substitution reaction of heteroaryl-metal unit and phosphine chlorides. At present, for the phosphonation of C­(sp 2 )–H bonds, a number of catalytic systems based on palladium, copper, and silver have been developed by several groups . Along with the development of auto-oxidative C­(sp 2 )–P formation, Wu and co-workers disclosed a direct phosphorylation of thiazole and quinoxaline derivatives induced by oxygen under metal-free and solvent-free conditions .…”

Transition‐Metal‐Free Regioselective C–H Bond Fluorination of 8‐Amidoquinolines with Selectfluor

“…In the past few years, the functionalization at the 5‐position of quinolines has been achieved by transition‐metal‐catalyzed remote C–H functionalizations, including those for halogenation, allylation, chalcogenation, sulfonylation, amination, nitration, and phosphonation . Most recently, a Ni‐catalyzed C‐5 fluorination of 8‐aminoquinolines by treatment with N ‐fluorobenzenesulfonimide (NFSI) was realized .…”

An efficient nickel/silver co-catalyzed remote C–H amination of 8-aminoquinolines with azodicarboxylates at room temperature

“… 13 Examples of silver catalysis in this kind of reactions are much less. 14 But the combination of these two metals created amazing results. 15 Within this paper, we report a highly efficient nickel/silver co-catalyzed C–H amination on C5 position of 8-aminoquinolines with azodicarboxylates at room temperature.…”