A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt

Ghosh, Prasanjit; Ganguly, Bhaskar; Perl, Eliyahu; Das, Sajal

doi:10.1016/j.tetlet.2017.05.091

Cited by 19 publications

(17 citation statements)

References 34 publications

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“…In 2017, Das and co‐workers reported a silver/copper‐cocatalyzed Liebeskind–Srogl cross‐coupling reaction . The transformation and a plausible reaction mechanism are shown in Scheme .…”

Section: Cui‐catalyzed Liebeskind–srogl Cross‐ Coupling Reactionsmentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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The Pd-catalyzed, Cu I Àcarboxylate-mediated crosscoupling reactiono fo rganosulfur compounds with nucleophilic organometallic reagents is knowna st he Liebeskind-Srogl cross-coupling reaction. Owing to the readily available starting materials and neutral reactionc onditions, it has become an attractive procedure for the formation of carbonÀcarbon bonds, in particularf or cases in whicht radi-tional methods had failed. Since the seminal work of Liebeskind and Srogl in 2000, this reactionh as received intense attentionf rom the synthetic community.I nt his Focus Review,w eh ighlight recent advances in this intriguing cross-coupling reactiona nd its applications in organic synthesis.Scheme1.Liebeskind-Srogl cross-coupling reaction.Scheme2.The original Liebeskind-Sroglc ross-coupling reaction.d ba = dibenzylideneacetone, TFP = tri-2-furanylphosphine [a] Dr.Scheme4.Cross-coupling reaction between a-amino acid thiol esters and organostannanes. Cbz = benzyloxycarbonyl.Scheme5.Cross-coupling reaction between thiol esters and B-alkyl-9-BBN. 9-BBN = 9-borabicyclo[3.3.1]nonane.Scheme6.One-pothydroboration/intramolecular-cross-couplingr eaction between thiol esters and B-alkyl-9-BBN. DIPEA = N,N-diisopropylethylamine.Scheme7.Cross-coupling reaction between thiol esters andorganoindium reagents.Scheme8.Cross-coupling reaction between thiol esters andorganosilicon reagents. TBAF = tetra-n-butylammonium fluoride.Scheme9.Intramolecular cross-coupling reaction between thiol esters and olefins.Scheme38. Cross-coupling reaction between diaryld isulfides and boronicacids/terminal-alkynes.Scheme55. Synthesis of the C 15 ÀC 36 segment of goniodomin A. TBS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl.Scheme56. To talsynthesis of verbenachalcone. MOM = methoxymethyl.Scheme57. Synthesis of enigmol and its stereoisomers. Boc = tert-butyloxycarbonyl.Scheme58. To talsynthesis of (À)-agelastatins A-F.Scheme59. Synthesis of quinone-containing salvinorin Aa nalogues.Scheme60. Synthesis of Soai-type aldehydes.

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Section: Cui‐catalyzed Liebeskind–srogl Cross‐ Coupling Reactionsmentioning

confidence: 99%

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

et al. 2018

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“…The product was obtained with the same spectral characterization as previously described. 55 1 H NMR (300 MHz, CDCl 3 ): δ 8.60 (t, J = 1.8 Hz, 1H), 8.43 (dd, J = 7.6, 2.3 Hz, 1H), 8.12 (dt, J = 7.9, 1.3 Hz, 1H), 7.73–7.67 (m, 3H), 7.33 (d, J = 7.6 Hz, 2H), 2.47 (s, 3H).…”

Section: Methodsmentioning

confidence: 99%

Aminobenzylated 4-Nitrophenols as Antibacterial Agents Obtained from 5-Nitrosalicylaldehyde through a Petasis Borono–Mannich Reaction

et al. 2018

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Multidrug-resistant bacteria are one of the current biggest threats to public health and are responsible for most nosocomial infections. Herein, we report the efficient and facile synthesis of antibacterial agents aminoalkylphenols, derived from 5-nitrosalicyladehyde and prepared through a Petasis borono–Mannich multicomponent reaction. Minimum inhibitory concentrations (MICs) as low as 1.23 μM for a chlorine derivative were determined for multidrug-resistant Gram-positive bacteria, namely, Staphylococcus aureus and Enterococcus faecalis , two of the main pathogens responsible for infections in a hospital environment. The most promising antibacterial agents were further tested against eight strains of four Gram-positive species in order to elucidate their antibacterial broadness. In vitro cytotoxicity assays of the most active aminoalkylphenol revealed considerably lower toxicity against mammalian cells, as concentrations one order of magnitude higher than the determined MICs were required to induce human keratinocyte cell death. The phenol moiety was verified to be important in deeming the antibacterial properties of the analyzed compounds, although no correlation between such properties and their antioxidant activity was observed. A density functional theory computational study substantiated the ability of aminoalkylphenols to serve as precursors of ortho -quinone methides.

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“…It has opened an avenue for the quest of newly functionalized quinolone moieties. Very recently, we have also reported Cu catalyzed synthesis of biaryl ketones from thiolester via Chan‐Lam cross coupling reaction . A variety of N ‐arylated heterocyclic motifs such as 2‐aminobenzimidazole and N ‐arylated amino phenols are found in numerous medicinally important compounds.…”

Section: Methodsmentioning

confidence: 99%

Ligand Free Approach for the Copper(II)‐Mediated C‐NH₂ Arylation of 4‐Quinolone Derivatives Under Ambient Condition

Ghosh

Das

2018

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A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt

Cited by 19 publications

References 34 publications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Aminobenzylated 4-Nitrophenols as Antibacterial Agents Obtained from 5-Nitrosalicylaldehyde through a Petasis Borono–Mannich Reaction

Ligand Free Approach for the Copper(II)‐Mediated C‐NH₂ Arylation of 4‐Quinolone Derivatives Under Ambient Condition

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A synthesis of biaryl ketones via the C–S bond cleavage of thiol ester by a Cu/Ag salt

Cited by 19 publications

References 34 publications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

The Liebeskind–Srogl Cross‐Coupling Reaction and its Synthetic Applications

Aminobenzylated 4-Nitrophenols as Antibacterial Agents Obtained from 5-Nitrosalicylaldehyde through a Petasis Borono–Mannich Reaction

Ligand Free Approach for the Copper(II)‐Mediated C‐NH2 Arylation of 4‐Quinolone Derivatives Under Ambient Condition

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Ligand Free Approach for the Copper(II)‐Mediated C‐NH₂ Arylation of 4‐Quinolone Derivatives Under Ambient Condition