C–H bond activation and ring oxidation in nickel carbahemiporphyrazines

Abstract

The first nickel complexes of two carbon-substituted phthalocyanine analogues are reported; both exhibit direct Ni-C bonding and oxygen activation chemistry is observed.

Benziporphyrins, a unique platform for exploring the aromatic characteristics of porphyrinoid systems

“…75 Subsequently, Elvidge and Golden reported the synthesis of a monobenziphthalocyanine 130. [77][78][79] For instance, reaction of 129 with Ni(COD) 2 in DMF-methanol gave a nickel(II) complex 131 and this underwent air oxidation to afford the phenolate complex 132 (Scheme 57). [77][78][79] For instance, reaction of 129 with Ni(COD) 2 in DMF-methanol gave a nickel(II) complex 131 and this underwent air oxidation to afford the phenolate complex 132 (Scheme 57).…”

“…76 The metalation of these systems has been investigated in detail and some of the resulting derivatives resemble those obtained for benziporphyrins. 79 Similarly, 130 reacted under the same conditions to yield nickel(II) complex 133. 79 Similarly, 130 reacted under the same conditions to yield nickel(II) complex 133.…”

Investigations into the Coordination Chemistry of 1,3-Bis(2’-benzimidazolyl­imino)isoindoline

“…[4][5][6][7][8][9] DII is a reactive species that can be easily modified through reaction with primary alkyl or aryl amines. [4][5][6][7][8][9][10][11][12][13] This property Сoordination Сhemistry of 1,3-Вis(2'-benzimidazolylimino)isoindoline is useful in formation of macrocycles and chelates for further metallation reactions. [14][15][16][17][18][19][20] DII can also be used in reactions with subphthalocyanine, [14][15][16][17][18][19][20] or for the production of phthalocyanine, [21] and hemiporphyrazines.…”

Metal Complexes of Carbaporphyrinoid Systems

“…NiA C H T U N G T R E N N U N G (COD) 2 in DMF/methanol reacted with 161 to give the nickel(II) complex 170 (Scheme 48). [110] As is the case for 167, two protons are relocated onto bridging nitro-gen atoms to give an overall neutral complex. Dicarbahemiporphyrazine 160 similarly reacted with NiA C H T U N G T R E N N U N G (COD) 2 to give the nickel(II) complex 171, and this reacted with molecular oxygen to afford the nonplanar phenolate complex 172 (Scheme 48).…”

“…Dicarbahemiporphyrazine 160 similarly reacted with NiA C H T U N G T R E N N U N G (COD) 2 to give the nickel(II) complex 171, and this reacted with molecular oxygen to afford the nonplanar phenolate complex 172 (Scheme 48). [110] 10. Miscellaneous Porphyrinoid Systems In addition to carbaporphyrins, an example of a nonaromatic carbacorrole 173 has been reported.…”