Copper-catalyzed cyanation of aryl halides with sodium nitroprusside in polyethylene glycol 400 (PEG-400)

Abstract

A simple and efficient CuI/PEG-400 catalytic protocol for the cyanation of aryl halides employing sodium nitroprusside, Na 2 [Fe(CN) 5 NO]·2H 2 O, as a new cyanation reagent was developed. The present cyanation reagent shows higher activity and gave the desired products in yields of up to 96%. In the present protocol, a variety of aryl bromides and iodides were cyanated smoothly with a wide range of substrate scope.

Copper-Mediated C–X Functionalization of Aryl Halides

“…In a similar study, Wang and co-workers showed that ethylenediamine in conjunction with Cu­(OAc) 2 .H 2 O could promote the cyanation of aryl bromides and activated aryl chlorides with K 4 [Fe­(CN) 6 ] in the presence of catalytic quantities of KI and Na 2 CO 3 . In addition, Chen and co-workers demonstrated Na 2 [Fe­(CN) 5 NO]·2H 2 O was a better reagent than K 4 [Fe­(CN) 6 ] for the cyanation of aryl iodides/bromides in PEG-400 solvent . In the presence of Na 2 [Fe­(CN) 5 NO]·2H 2 O, NaOH, and a catalytic amount of CuI (10 mol %), aryl iodides were converted into corresponding nitriles in good yields.…”

Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides

“…In this scenario, transition-metal catalyzed syntheses of aryl cyanides from aryl halides were explored and were found to be highly acceptable. Among them palladium, [12][13][14][15] nickel [16][17][18] and copper [19][20][21] catalyzed cyanation have been well explored. Takagi et al in 1973 introduced the rst palladium-catalyzed cyanation from bromo and iodoarenes using potassium cyanide.…”

Triple Action of an Attractive Deep Eutectic Solvent in the Synthesis of Aryl Nitriles and Substituted Triazoles Using a Magnetically Reusable Fe3O4@SiO2@PrNCu Catalyst

“…[b] Yields refer to the isolated pure products and the structures of the products were confirmed by 1 H NMR and 13 C NMR spectral data [6f,8a–c,f] (Refer to ESI).…”

“…[a] Reaction conditions: arylhalide (1 mmol), K 4 [Fe(CN) 6 ] (0.2 mmol), DMED/TBAB (4 mL) and Fe 3 O 4 @SiO 2 @PrNCu (0.2 mol%) at 80 °C. [b] Yields refer to the isolated pure products and the structures of the products were confirmed by 1 H NMR and 13 C NMR spectral data [6f,8a–c,f] (Refer to ESI). [c] Reaction was carried out using 0.5 mol% of Fe 3 O 4 @SiO 2 @PrNCu catalyst.…”