A New Indirect Application of Aggregative Activation: Synthesis of Esters by Cobalt-Catalyzed Carbonylation of Aryl, Heterocyclic, and Vinyl Halides under Atmospheric Pressure

Marchal, J.; Bodiguel, Jacques; Fort, Yves; Caubère, P.

doi:10.1021/jo00131a005

Cited by 29 publications

(15 citation statements)

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“…Soc., Vol. 45, No.4, 1998 455 This hypothesis was completely verified 17. Thus (Scheme XIII) MeOH was added to a CoCRACO prepared in THF.…”

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confidence: 83%

Aggregative Activation in Connection with a Few Reactions Using Transition or Alkali Metal Derivatives as Intermediates

Caubère¹

1998

J Chinese Chemical Soc

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Aggregative Activation principles are given. The first application described deals with the preparation ofreducing agents used to perform couplings and carbonylations of aryl and hetaryl halides. The second application deals with the preparation of two kind of super bases: sodium amide and butyllithium containing complex bases. The arynic synthesis of indoles is given as an illustration of the use of the first kind of base while the rnetalation of pyridine derivatives exemplifies the use of the second. In this latter case, a new metalation radical mechanism is proposed.

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“…Soc., Vol. 45, No.4, 1998 455 This hypothesis was completely verified 17. Thus (Scheme XIII) MeOH was added to a CoCRACO prepared in THF.…”

mentioning

confidence: 83%

Aggregative Activation in Connection with a Few Reactions Using Transition or Alkali Metal Derivatives as Intermediates

Caubère¹

1998

J Chinese Chemical Soc

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“…The intensively stirred mixture was Table 2 Selected interatomic distances (Å ) and angles (8) for 7a and 9. 7) 120.4(2) -C(2)-C(7)-C (6) 123.2(2) - Fig. 1.…”

Section: Preparation Of Potassium Tetracarbonylcobaltate Kco(co) 4 Somentioning

confidence: 99%

“…The reaction occurs in the presence of tetracarbonylcobaltate anion and corresponds to the S N 2 mechanism [1][2][3][4]. The activation of aryl halides requires special techniques, including the UV irradiation, the system enrichment with a one-electron reducing agent, or the modification of the Co(CO) 4 À anion [5][6][7][8][9][10][11][12][13][14]. All these early studies demonstrate the ability of the Co(CO) 4 À anion to be an efficient catalyst for the carbonylation of aryl halides in conditions that provide the anion-radical synthetic pathway.…”

Section: Introductionmentioning

confidence: 99%

Chemoselectivity of cobalt-catalysed carbonylation—A reliable platform for the synthesis of fluorinated benzoic acids

Boyarskiy

Fonarı

Khaybulova

et al. 2010

Journal of Fluorine Chemistry

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“…The reaction of aryl halide methoxycarbonylation catalysed with alkyl cobalt carbonyl complexes (Scheme 1) provides an interesting model to study the principles of the radical anion transformations in aryl halides [16,17,18,19,20,21,22,23].…”

Section: Introductionmentioning

confidence: 99%

“…The authors proposed the radical anion mechanism for this reaction. Later it was shown that photochemical initiation can be used in the carbonylation of bromobenzenes instead of a one-electron reducing agent (NaH) [20,26,27,28].…”

Section: Introductionmentioning

confidence: 99%

Cobalt-Catalyzed Methoxycarbonylation of Substituted Dichlorobenzenes as an Example of a Facile Radical Anion Nucleophilic Substitution in Chloroarenes

et al. 2014

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A thorough mechanistic study on cobalt-catalysed direct methoxycarbonylation reactions of chlorobenzenes in the presence of methyl oxirane on a wide range of substrates, including poly-and monochloro derivatives with multiple substituents, is reported. The results demonstrate that the reaction is potentially useful as it proceeds under very mild conditions (t = 62 °C, P CO = 1 bar) and converts aryl chlorides to far more valuable products (especially ortho-substituted benzoic acids and esters) in high yields. This transformation also offers another opportunity for the utilization of environmentally harmful polychlorinated benzenes and biphenyls (PCBs). This study is the first to discover an unexpected universal positive ortho-effect: the proximity of any substituent (including Me, Ph, and MeO groups and halogen atoms) to the reaction centre accelerates the methoxycarbonylation in chlorobenzenes. The effect of the ortho-substituents is discussed in detail and explained in terms of a radical anion reaction mechanism. The advantages of the methoxycarbonylation as a model for the mechanistic study of radical anion reactions are also illustrated.

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A New Indirect Application of Aggregative Activation: Synthesis of Esters by Cobalt-Catalyzed Carbonylation of Aryl, Heterocyclic, and Vinyl Halides under Atmospheric Pressure

Cited by 29 publications

References 0 publications

Aggregative Activation in Connection with a Few Reactions Using Transition or Alkali Metal Derivatives as Intermediates

Aggregative Activation in Connection with a Few Reactions Using Transition or Alkali Metal Derivatives as Intermediates

Chemoselectivity of cobalt-catalysed carbonylation—A reliable platform for the synthesis of fluorinated benzoic acids

Cobalt-Catalyzed Methoxycarbonylation of Substituted Dichlorobenzenes as an Example of a Facile Radical Anion Nucleophilic Substitution in Chloroarenes

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