Palladium-catalyzed meso-amination and amidation of porphyrins: marked acceleration with the Ni(II) central metal ion

Takanami, Toshikatsu; Hayashi, Masako; Hino, Fumio; Suda, Kohji

doi:10.1016/s0040-4039(03)01837-9

Cited by 64 publications

(24 citation statements)

References 11 publications

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“…Dehalogenation of 154 with four equivalents of AgBF 4 gave the tetracationic aqua species 155, which was subsequently treated with 5-pyridyl-10,15,20-triphenylporphyrin to give the pentameric porphyrin assembly 156 in quantitative yield. A nonameric porphyrin array (157) was also obtained quantitatively from 155 and four equivalents of a cyanobisporphyrin. There is no appreciable communication between Scheme 26.…”

Section: Miscellaneous Porphyrinsmentioning

confidence: 99%

Merging Porphyrins with Organometallics: Synthesis and Applications

2008

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The coordination chemistry of porphyrins has traditionally involved the ability of the porphyrin's tetrapyrrolic core to accommodate metal ions of varying charges and sizes, and on the organometallic chemistry of the resulting metalloporphyrins. However, the organometallic chemistry of porphyrins is not necessarily restricted to the metal bound in the porphyrin core, but can also be extended to the porphyrin periphery, be it through direct metalation of the porphyrin macrocycle at the meso or β position, or by attachment to or merger of the porphyrin skeleton with ligands, followed by metalation. This Review focuses on the synthetic strategies used for porphyrins with peripheral metal–carbon bonds. The exciting results that have been produced underscore the importance and future potential of this field.

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Section: Miscellaneous Porphyrinsmentioning

confidence: 99%

Merging Porphyrins with Organometallics: Synthesis and Applications

2008

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“…The intolerance of the transition metal catalyst (especially copper) toward free‐base porphyrins is a further problem, due to undesired metal‐insertion reactions. Therefore, zinc porphyrins, which can readily be demetallated under acidic conditions, have frequently been used; however, it should be noted that zinc ions decrease the reactivities of porphyrins . Limited alternative approaches involving the oxidation before or after nucleophilic substitution were also reported ,…”

Section: Introductionmentioning

confidence: 99%

Versatile and Catalyst‐Free Methods for the Introduction of Group‐16 Elements at the meso‐Positions of Diarylporphyrins

et al. 2018

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This report describes versatile and catalyst-free methods for the introduction of group-16 elements at the meso-positions of diarylporphyrins. The methods involve nucleophilic aromatic substitution (S N Ar) of the meso-bromodiarylporphyrin. The reaction proceeds in almost quantitative yield in most cases. Reactions with various phenols afford the corresponding meso-phenoxyporphyrins, except for the reaction with 4-hydroxypyridine, which affords a meso-(N-pyridonyl)porphyrin. With the exception of thiocyanate, reac-tions involving sulfur-centered nucleophiles proceed smoothly and afford the corresponding functionalized porphyrins, including a meso-sulfonylporphyrin that was obtained from benzenesulfinate. To overcome problems associated with the handling of chalcogenols (instability, bad odors), we also used dichalcogenides as nucleophile precursors to afford the corresponding meso-sulfanyl or selanylporphyrins. The instability of a novel meso-tellanylporphyrin is also revealed.[a] Dr.

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“…[10] In the same 2003 Suda studied Pd-catalyzed amination reactions of meso-bromosubstituted porphyrins using Pd(0) and Pd(II) catalysts with a variety of phosphine ligands. [11] Lier claimed first catalytic amination of Zn complexes of mono-and di-β-halogenoporphyrins with aliphatic and aromatic amines in 2001. [12] Zhang was the first who employed Pd(OAc) 2 for di-and tetraamination of bis-and tetrakis(4-bromophenyl) susbstituted porphyrins.…”

Section: Introductionmentioning

confidence: 99%

“…[13] The year of 2003 was extremely fruitful for the pioneer works in the field of C-N bond formation in porphyrin series: Suda reported amidation of Zn and Ni meso-bromoporphyrin complexes with primary and secondary amides in the presence of Pd(OAc) 2 /BINAP. [14] Zhang modified this method applying Pd(OAc) 2 /Xantphos system which allowed diamidation of di-meso-bromoporphyrins in high yields. [15] In 2001 amidation of β-bromoporphyrins using cyclic amides in the presence of Pd(dppf)Cl 2 /dppf was reported by Lier, [12] and in 2007 Zhang proposed an universal approach for the amidation of mono-and dibromoporphyrins and their metal complexes using Pd 2 (dba) 3 or Pd(OAc) 2 with Xantphos ligand.…”

Section: Introductionmentioning

confidence: 99%