An Investigation into Causes and Effects of High Cyanide Levels in the Palladium-Catalyzed Cyanation Reaction

Abstract

[reaction: see text] The palladium-catalyzed cyanation reaction is known to be sensitive to dissolved cyanide. Investigation into some causes of high levels of dissolved cyanide is presented here, along with a robust solution to this problem.

Synthesis of a 14C‐labeled FPTase inhibitor via a Pd‐catalyzed cyanation with Zn(14CN)2 and via bromo[14C]acetic acid

“…11 The aryl halides include iodide, bromide and even chloride. 12 Current methodology involving transition metal mediated cyanation reaction has been widely used in both organic and medicinal chemistry. 13 We found Zn( 14 CN) 2 to be an attractive reagent for the preparation of the compound containing benzo[…”

Modern Synthetic Approaches to Phthalonitriles with Special Emphasis on Transition-Metal Catalyzed Cyanation Reactions

“…If all Zn(CN) 2 is added at once, then no phthalonitrile could be obtained, because in this case excess of free cyanide-ion sequesters Pd catalyst. [37] Pd-catalyzed cyanation was also applied to prepare polycyanated compounds -precursors to olygomeric phthalocyanines. Thus, Hanack et al performed treatment of hexabromotriphenylene with KCN in the presence of 18-crown-6 and Pd(PPh 3 ) 4 in 2-chloronaphthalene (2-ClN).…”

Bis[tri(o-tolyl)phosphine]palladium

“…Cyanozinc reagents have been used for the cyanation of aryl halides. 82 Organogermanes have also been used as alternative transmetallating agents. 83 Vinylsilanes can be prepared from the palladium-catalyzed reaction of the corresponding enol phosphates and either an organomagnesium or organoaluminum reagent (eq 21).…”