A convenient and efficient procedure for the palladium-catalyzed cyanation of aryl halides using trimethylsilylcyanide

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

“…The mixture was extracted with ethyl ether (3 × 10 mL). The combined ethyl ether extracts were washed with brine, dried over Na 2 SO 4 , filtered and evaporated under reduced pressure; the residue was purified by flash column chromatography (ethyl acetate / petroleum ether mixture as eluate) to afford the desired products 2 ( Table 2 entries [11][12][13][14][15][16][17]. …”

Endocyclic Extension of Porphyrin π‐System by Interior Functionalization of N‐Confused Porphyrins

“…Besides, the absence of accessible sp 2 carbon atoms within the endocyclic part in regular porphyrins is another fundamental problem. That is to say, an interior functional group is connected to a macrocycle through an sp 2 nitrogen atom, which is not involved in the [18]annulenic substructure in a regular porphyrin, and thus only weak interaction between the interior functional group and the porphyrin p-system is to be expected.…”

“…[5] Confusion of a pyrrole ring in a regular porphyrin affords an N-confused porphyrin (NCP), [6] which is an isomer of the porphyrin and also a kind of carbaporphyrin. [7] In the case of an NCP, an interior functional group can be connected through an sp 2 carbon atom, which is involved in the [18]annulenic substructure. As a result, strong interaction between the interior functional group and the porphyrin p-system is to be expected.…”

Iron(II)‐Catalyzed Direct Cyanation of Arenes with Aryl(cyano)iodonium Triflates

“…[3] However, both reactions require toxic copper(I) cyanide as the cyano source and occur under rather harsh reaction conditions. The nucleophilic cyanation of aryl halides under the catalysis of transition metals with KCN or NaCN, [4] Zn(CN) 2 , [5] acetone cyanohydrin, [6] trimethylsilyl cyanide, [7] and K 4 [Fe(CN) 6 ] [8] as cyanating agents has emerged as an alternative route to aryl nitriles. Moreover, directing-group-assisted transition-metal-catalyzed C À H bond functionalization has enabled the direct cyanation of aromatic CÀH bonds.…”