Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Ketones

Quan, Long Guo; Gevorgyan, Vladimir; Yamamoto, Yoshinori

doi:10.1021/ja983645w

Cited by 141 publications

(41 citation statements)

References 17 publications

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“…Later an analogous catalytic (palladium acetate) route to 1H-inden-1-ols (including 2a and 2c) directly from alkyne and o-bromoacetophenone was reported [8] for conditions very similar to those reported much earlier [9] for Pd(OAc) 2 -catalysed indenone synthesis from ortho-iodobenzaldehyde and diaryl ketones. More recently, high-yield cobalt-catalysed formation of 1H-inden-1-ols (including 2a and 2c) has been reported [10] for alkynes with o-iodoacetophenone using Co(Ph 2 PCH 2 CH 2 PPh 2 )I 2 and zinc in acetonitrile at 80°C; unsymmetrical alkynes gave similar regiochemistry patterns to those reported here.…”

Section: Indenone Formationmentioning

confidence: 65%

“…Reaction of g 2 -(2-benzoylphenyl)tetracarbonylmanganese (1b) with diphenylacetylene to form 1,2,3-triphenylinden-1-ol (2j) 1b (0.122 g, 0.350 mmol) and diphenylacetylene (0.065 g, 0.365 mmol) in benzene under reflux over 18 h gave Mn 2 (CO) 10 (0.010 g, 18%) and 2j (0.107 g, 85%) as a colourless oi1, pure by NMR, identified by NMR only [8]. 1 H NMR: d 7.90 (m, 19H).…”

Section: With Bis(trimethylsilyl)acetylene To Form 1-methyl-23-bis(tmentioning

confidence: 99%

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Indenols, indenones and (arylcyclohexadienyl)Mn(CO)3 π-complexes from the thermally promoted reactions of alkynes with ortho-Mn(CO)4 aryl ketone, amide, ester and aldehyde derivatives

Robinson

Depree

Wit

et al. 2005

Journal of Organometallic Chemistry

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Section: Indenone Formationmentioning

confidence: 65%

Section: With Bis(trimethylsilyl)acetylene To Form 1-methyl-23-bis(tmentioning

confidence: 99%

Indenols, indenones and (arylcyclohexadienyl)Mn(CO)3 π-complexes from the thermally promoted reactions of alkynes with ortho-Mn(CO)4 aryl ketone, amide, ester and aldehyde derivatives

Robinson

Depree

Wit

et al. 2005

Journal of Organometallic Chemistry

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“…7.18) [51]. This nucleophilic behavior of Pd(II) species [52] was triggered by the specific reaction conditions and particularly by the presence of water. Indeed, in the absence of water, the arylpalladium(II) complex returned to its usual electrophilic behavior and the reaction proceeded by sequential ortho-arylation/a-arylation of the ketone to provide phenanthrene derivatives (vide infra).…”

Section: Aromatic Arylations Coupled With Addition To C=o or C=n Bondsmentioning

confidence: 98%

Bibliographical Background: The Ortho Effect in The Catellani Reaction

Larraufie

2013

Development of New Radical Cascades and Multi-Component Reactions

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Pallado-catalyzed sequential reactions involving direct C-H bond activations have emerged as powerful tools for rapid access to complex polycyclic scaffolds, starting from simple precursors [1][2][3]. In this context, Professor Marta Catellani has pioneered in the mid 1980s the utilization of norbornene in cooperation with palladium to achieve sequential C-halide and C-H activations via the formation of a five-membered alkylaromatic palladacycle. In 1985, she published the synthesis of dihydrophenanthrene 1 by coupling of two molecules of bromobenzene and one of norbornene, through the proposed formation of palladacycle 2 ( Fig. 7.1) [4].Since then, numerous applications of palladium/norbornene-mediated domino processes have been reported, allowing the synthesis of various polycyclic frameworks and the construction of up to three carbon-carbon bonds in a single reaction [5][6][7]. The catalytic cycle of the Catellani reaction, involving multiple oxidation state of palladium (0, II and potentially IV), will be presented first. Several examples of the synthetic scope of this methodology will follow, with a special focus on the sequences involving aryl-aryl coupling. Palladacycle FormationThe Catellani reaction is based on the formation of palladium(II) metallacycles 7 and their ability to react with electrophiles such as aryl and alkyl halides. The palladacycle is generated from palladium(0) complex 3, aryl halide 4 and norbornene. Generally, Pd(0) catalysts are not air stable, so the in situ generation of Pd(0) species by reaction of palladium(II) salts with phosphines [8,9]

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“…On the other hand, as previously described 9 , the stoichiometric reaction of palladium (II) complexes of 2-acylaryl with alkynes affords indenol derivatives. Moreover, carbocyclization of ortho-haloaromatic ketones or aldehydes with alkynes leads to substituted indenols 10 . More recently 11 , it has been reported that the regioselective rhodium-catalyzed carbocyclization reaction of orthoformylphenylboronic acid with alkynes is considered a promising way to produce substituted inden-1-ol derivatives.…”

Section: Introductionmentioning

confidence: 99%

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

et al. 2014

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An elegant one-pot synthesis of new indenols 2 was successfully carried out, starting from 1-hydroxy-1H-indene-2-carboxylic acid 1. Thus, esterification of acid 1 with aliphatic alcohols in toluene at reflux and a catalytic amount of para-toluenesulfonic acid afforded the corresponding alkyl esters 2 in moderate to good yields. This classical esterification process enables an efficient entry to a variety of new indenol-based molecular models 2, which could be adapted to a range of drug candidates. All the synthesized compounds 2a-e were subjected to the preliminary evaluation for their potential anti-oxidant and anti-bacterial activities. The assessment of radical scavenging capacity of the compounds 2a-e towards the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) was measured and these compounds were found to scavenge DPPH free radical efficiently. Moreover, the in vitro antibacterial activity of derivatives 2a-e has been tested against a panel of pathogenic agents to show potent activity against all sensitive and resistant ones.

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Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Ketones

Cited by 141 publications

References 17 publications

Indenols, indenones and (arylcyclohexadienyl)Mn(CO)3 π-complexes from the thermally promoted reactions of alkynes with ortho-Mn(CO)4 aryl ketone, amide, ester and aldehyde derivatives

Indenols, indenones and (arylcyclohexadienyl)Mn(CO)3 π-complexes from the thermally promoted reactions of alkynes with ortho-Mn(CO)4 aryl ketone, amide, ester and aldehyde derivatives

Bibliographical Background: The Ortho Effect in The Catellani Reaction

A facile approach towards the synthesis of functionalized indenol derivatives identified as potent anti-oxidant and anti-bacterial agents

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