Reversible migration of an axial carbene ligand into an iron-nitrogen bond on a porphyrin. Implications for high oxidation states of heme enzymes and heme catabolism

Latos-Grazynski, L.; Cheng, Richard P.; Mar, Gerd N. La; Balch, Alan L.

doi:10.1021/ja00404a059

Cited by 60 publications

(34 citation statements)

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“…the adduct results from the insertion of a carbene into the FeÀN bond, as already described [10]. Mechanistic Considerations and Spectroscopic Features of the Products.…”

mentioning

confidence: 82%

“…4, 124.9, 126.6, 127.37, 127.40, 127.5, 127.6 (C m (Ph), C p (Ph)); 128.0 (C (7), C(18)); 129.6 (C(12), C(13)); 132.6 (C o (PhÀC (5) and ÀC(20)); 133. 5 (C(8), C (17)); 133.56 (C o (PhÀC (10) and ÀC (15)); 133.58 (C o (PhÀC(5), ÀC (10), ÀC (15), and ÀC (20)); 142. 6, 146.8, 148.2, 153.7, 157.0 (C(a)); 173.7 (C¼O).…”

Section: Experimental Partmentioning

confidence: 99%

“…1, 121.5, 126.5 (C m (Ph), C p (Ph)); 126.46, 126.53, 126.9 (C m (Ph), C p (Ph)); 128. 1, 131.5, 131.9, 132.0, 132.5 (C(b)); 133.2 (C o (PhÀC(20)); 134.37, 134.40 (C o (PhÀC (5), ÀC (10), and ÀC (15)); 135.2 (C(3)); 138.0, 142. 6, 142.7, 142.9, 148.2, 150.1, 150.2, 150.4, 151 [2 1 ,12 10,15,3,12,l]porphyrinato]zinc(II) (¼ [Diethyl 1a,9a,10a,8,12,10H,19H,l]porphine-1,10-dicarboxylato(2 À)-kN 19 [(2r,2 1 t,3c)-2 1 -(Ethoxycarbonyl)-5,10,15,20-tetrakis(3-methoxyphenyl)-2,3-dihydrocyclopropa[b]porphyrinato]zinc(II) 1 ) (¼ [Ethyl (1a,1aa,8,13, …”

Section: Experimental Partmentioning

confidence: 99%

“…The d that occur between d(H) 8.50 and 8.60 and between d(H) 8.00 and 8.37 are assigned to the resonance of HÀC (8) and HÀC (17), and to HÀC (7) and Scheme 4 HÀC(18), resp. These attributions are established by the NOESY correlations between the signals of the H o -atoms of ArÀC (10) and ÀC (15) and the signals of HÀC (8) and HÀC (17), and of HÀC (12) and HÀC (13). In the case of the trans-cyclopropanes 2a -c, the cyclopropane H-atoms give rise to a 3 J of ca.…”

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confidence: 99%

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A New Insight into the Catalytic Decomposition of Ethyl Diazoacetate in the Presence of meso‐Tetraarylporphyrin (=5,10,15,20‐Tetraaryl‐21H,23H‐porphine) Complexes

Gomes¹,

Leão²,

Alonso³

et al. 2008

Helvetica Chimica Acta

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The decomposition of ethyl diazoacetate by several catalysts in the presence of meso‐tetraarylporphyrin complexes with different electronic features was evaluated. The distribution of the obtained products (chlorins, bacteriochlorins, isobacteriochlorins, and porphyrin derivatives resulting from CH insertion and Büchner ring expansion) is dependent on the catalyst and on the electronic features of the meso‐aryl groups.

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“…the adduct results from the insertion of a carbene into the FeÀN bond, as already described [10]. Mechanistic Considerations and Spectroscopic Features of the Products.…”

mentioning

confidence: 82%

Section: Experimental Partmentioning

confidence: 99%

Section: Experimental Partmentioning

confidence: 99%

mentioning

confidence: 99%

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A New Insight into the Catalytic Decomposition of Ethyl Diazoacetate in the Presence of meso‐Tetraarylporphyrin (=5,10,15,20‐Tetraaryl‐21H,23H‐porphine) Complexes

Gomes¹,

Leão²,

Alonso³

et al. 2008

Helvetica Chimica Acta

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“…Upon a one-electron oxidation of the vinylidene carbene complex (7), the electrophilic vinylidene ligand is no longer (8) which is transformed into the N-vinylporphyrin (9) upon protonolysis of the iron-carbon bond. The N,Nf-bridged vinylidene porphyrin (10) is generated upon a further one-electron oxidation with FeC13 (9,(16)(17)(18).…”

Section: N/' Hmentioning

confidence: 99%

Organometallic aspects of cytochrome P-450 metabolism

Setsune¹,

Dolphin²

1987

Can. J. Chem.

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On a dkmontrk que les porphyrines likes au carbene-fer, des porphyrines lites au mkthylkne-fer par une liaison N-Fe, les porphyrines likes des N-alkyl-fer et les porphyrines likes a des a-alkyl-fer se retrouvent toutes dans la nature et qu'elles se transfoment les unes dans les autres par des rkactions rkdox. On passe en revue la chimie des porphyrines lites au fer ainsi que celle de porphyrines modeles likes au fer, au cobalt et au ruthknium en faisant ressortir leur chir&e organomktallique.[Traduit par la revue]

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Cobalt Silylenes as Platforms for Catalytic Nitrene‐Group Transfer by Metal–Ligand Cooperation.

et al. 2022

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A cobalt silylene (Co=Si) linkage enables a distinct metal/ligand cooperative activation of an organic azide, where nitrene transfer occurs to and from the Co⋅⋅⋅Si linkage without ligand dissociation from the 18‐electron cobalt center. This process utilizes the orthogonal binding affinities of the silicon and cobalt sites to avoid CO poisoning that would otherwise inhibit reactivity, leading to significantly improved catalytic isocyanate generation compared with related systems. The dual‐site approach demonstrates the potential of metal/main‐group bonds to access new and efficient catalytic pathways.

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Reversible migration of an axial carbene ligand into an iron-nitrogen bond on a porphyrin. Implications for high oxidation states of heme enzymes and heme catabolism

Cited by 60 publications

References 1 publication

A New Insight into the Catalytic Decomposition of Ethyl Diazoacetate in the Presence of meso‐Tetraarylporphyrin (=5,10,15,20‐Tetraaryl‐21H,23H‐porphine) Complexes

A New Insight into the Catalytic Decomposition of Ethyl Diazoacetate in the Presence of meso‐Tetraarylporphyrin (=5,10,15,20‐Tetraaryl‐21H,23H‐porphine) Complexes

Organometallic aspects of cytochrome P-450 metabolism

Cobalt Silylenes as Platforms for Catalytic Nitrene‐Group Transfer by Metal–Ligand Cooperation.

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