Progress in the Synthesis and Derivatization of Norcorrole

doi:10.6023/cjoc202202039

Abstract

In recent years, norcorrole has attracted extensive attention of scientific researchers, owing to its distinct paratropic ring current, high single molecule conductivity, narrow HOMO-LUMO gap, stable redox performance and unique chemical reactivity. The different synthetic methods of norcorrole in recent years are reviewed, with emphasis on the derivatization reactions in four aspects: insertion, substitution, redox and extension of π conjugated system, and the development of norcorrole is prospected.

Key words: norcorrole, synthesis, derivatization, antiaromaticity

Cite this article

Sha Li, Yahan Sun, Yankui Meng, Xiaofang Li, Shaowei Zhang. Progress in the Synthesis and Derivatization of Norcorrole[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2390-2405.

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Fig. & Tab. 37

Figure 1. Generic structures of porphyrin, corrole and norcorrole (the bold lines show the conjugation circuits)

Scheme 1. Nickel-mediated reductive homocoupling of dipyrrin complex 1 to NiII norcorrole 2

Scheme 2. Structures and synthesis of meso-aryl-substituted norcorroles 2a~2i

Scheme 3. Structures and synthesis of meso-alkyl-substituted norcorroles 2j~2m

Scheme 4. Synthesis of NiII benzonorcorroles TBNc and DBNc

Scheme 5. Synthesis of copper norcorrole 7

Scheme 6. Synthesis of the metal-free norcorrole, palladium norcorrole and norcorrole P(V) complex

Scheme 7. Metal-templated intermolecular homocoupling of α,α'-dibromodipyrrin complexes to octaphyrin 11

Scheme 8. Concentration-dependent formation of 12 from 1

Scheme 9. Reactions of NiII porphyrin 13 and NiII norcorrole 2 with stable silylene 14

Scheme 10. Silylene transfer from silacyclopropane 17 to norcorrole 2

Scheme 11. Reaction of NiII norcorrole 2 with in-situ-generated dichlorocarbene

Scheme 12. Reactions of 3-nitronorcorrolatonickel(II) with dialkyl acetylenedicarboxylates and hydrolysis of the meso-substituent in 22-R

Scheme 13. Amination of NiII norcorrole 2 and dissociation of 26 into monomer radical

Scheme 14. Singlet-triplet equilibrium in 27

Scheme 15. Synthesis of azacorrole from norcorrole 2 and amine with the presence of PhIO

Scheme 16. Cyanation of norcorrole 2 with potassium cyanide

Scheme 17. Substitution of norcorrole 2 with thiophenol

Scheme 18. Substitution of norcorrole 2 with thiophenol and phenol

Scheme 19. Synthesis of the amino norcorroles

Scheme 20. Reaction of norcorrole 2 with active methylene compounds

Scheme 21. Reaction of norcorrole 2 with NHC

Scheme 22. Nitration of the norcorrole ring with isoamyl nitrite

Scheme 23. Bromination of norcorrole 2 and Rearrangement of bromonorcorroles 47 and 48

Scheme 24. Suzuki-Miyaura cross-coupling and Migita-Kosugi-Stille coupling of bromonorcorroles 47 and 48

Scheme 25. Octabromination and octaalkynylation of norcorrole 2

Scheme 26. Friedel-Crafts acylation of norcorrole 2

Scheme 27. Oxidation of norcorrole

Scheme 28. Oxidative ring cleavage of norcorrole 2

Scheme 29. Deprotection of 61e and keto-enol tautomerization between 62 and 62'

Scheme 30. Hydrogenation of norcorrole 2 by Raney Ni

Scheme 31. Hydrogenation of norcorrole 2 by TsNH2NH2

Scheme 32. Synthesis of norcorrole radical anion

Scheme 33. Cycloaddition of iminonitriles to norcorrole

Scheme 34. Synthesis of pyridine-fused bis(norcorrole)

Scheme 35. Resonance forms of pyridine-fused bis(norcorrole)

Scheme 36. Synthesis of doubly linked norcorrole dimer

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