Mechanistic Development and Recent Applications of the Chan–Lam Amination

West, Matthew J.; Fyfe, James W. B.; Vantourout, Julien C.; Watson, Allan J. B.

doi:10.1021/acs.chemrev.9b00491

Cited by 326 publications

(250 citation statements)

References 234 publications

(653 reference statements)

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“…The reaction mechanism . Although increasing numbers of studies presume a Cu(I)/Cu(III) catalytic cycle in the CEL reactions (Scheme ), the limited stability of most Cu(III) complexes with the routine ligands makes their direct detection difficult. Whereas Cu(I) and Cu(II) complexes are the most common species in chemistry, the number of well‐defined organometallic copper(III) complexes is very restricted.…”

Section: Resultsmentioning

confidence: 99%

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

et al. 2020

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In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan‐Evans‐Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4‐t‐butyl‐2,5‐bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter‐anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C−N‐bond formation. Forty‐three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C−N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C−N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C−N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).

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Section: Resultsmentioning

confidence: 99%

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

et al. 2020

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“…These observations implicate a substantially different reactivity type in the present N-terminal reactivity. 36,37 To determine the tolerance of the reaction for different Nterminal residues, we synthesized variants at the N-terminal residue (5-13, Table 2). The reaction tolerates a wide variety of N-terminal residues (entries 1-5, 7-11), including bulky residues (tryptophan, valine, and leucine), charged residues (arginine, aspartate) and glycine.…”

Section: Resultsmentioning

confidence: 99%

Copper-mediated peptide arylation selective for the N-terminus

et al. 2020

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“…42 The pharmacological activity of cappariloside A lay in broad-spectrum antiviral efficacy and impairing the upregulations of proinflammatory factors in host cells induced by the influenza virus. 44 In addition, the arylation of compound 8 afforded the phenylsubstituted analog 16 through Chan-Lam-Evans coupling reaction 45 and hydrolysis reaction ( Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Multigram Scale Synthesis and Anti-Influenza Activity of 3-Indoleacetonitrile Glucosides

Dong

Yan

et al. 2020

Natural Product Communications

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Indole-3-acetonitrile-6- O-β-d-glucopyranoside 1 is a simple alkaloid with anti-influenza A virus activity extracted from Radix isatidis. Herein, a concise and practical total synthetic route of 1 was presented, starting from 6-benzyloxyindole on a multigram scale. The pivotal reaction sequence involved the Mannich reaction, the fluoride ion-induced elimination-addition reaction, and phase-transfer-catalyzed glycosylation reaction as key steps. In addition, compounds 1 and two modified derivatives 8 and 16 were tested for anti-influenza efficacy and cytotoxicity in vitro performed on Madin-Darby canine kidney cells. The results revealed that the compounds exerted antiviral activity against the influenza A virus to a certain extent and displayed no cytotoxicity. These findings could contribute to the development of traditional Chinese medicine R. isatidis for treating the influenza virus.

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Mechanistic Development and Recent Applications of the Chan–Lam Amination

Cited by 326 publications

References 234 publications

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

Chan‐Evans‐Lam C−N Coupling Promoted by a Dinuclear Positively Charged Cu(II) Complex. Catalytic Performance and Some Evidence for the Mechanism of CEL Reaction Obviating Cu(III)/Cu(I) Catalytic Cycle

Copper-mediated peptide arylation selective for the N-terminus

Multigram Scale Synthesis and Anti-Influenza Activity of 3-Indoleacetonitrile Glucosides

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