Recent improvements in the alkoxycarbonylation reaction catalyzed by transition metal complexes

Kalck, Philippe; Urrutigoı̈ty, Martine

doi:10.1016/j.ica.2015.02.007

Cited by 66 publications

(36 citation statements)

References 124 publications

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“…Carbonylations of alkenes, such as hydroformylation 2 and alkoxycarbonylation 3 play a central role in the production of bulk chemicals. However, their use in small laboratory synthetic applications is more rare, because of the toxicity of CO and advanced technical requirements.…”

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confidence: 99%

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

2015

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Herein, we report a Pd-catalysed alkoxycarbonylation of alkenes based on the use of a recyclable CO2 reduction product, the crystalline and air-stable N-formylsaccharin, as a CO surrogate. The carbonylation proceeds under ambient conditions in an exceptionally complementary regioselective fashion yielding the desired branched products from styrene derivatives and valuable linear esters from alkyl-substituted alkenes.

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confidence: 99%

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

2015

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“…Palladium-catalyzed alkoxycarbonylation reaction was recently reviewed considering, among improvements, the use of alternative solvents (ILs, scCO2) and MW heating [60]. It is worth marking the asymmetric Pd(II)-catalysedoxycarbonylation of racemic pent-4-ene-1,3-diol by kineticresolution in ILs using a chiral ligand for palladium.…”

Section: Transition Metal-catalyzed C-ccoupling Reactionsmentioning

confidence: 99%

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

et al. 2017

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Abstract:The quest for sustainable processes is becoming more and more important, with catalysis playing a major role in improving atom economy and reducing waste. Organic syntheses with less need of protecting/de-protecting steps are highly desirable. The combination of microwave irradiation, as energy source, with ionic liquids, as both solvents and catalysts, offered interesting solutions in recent years. The literature data of the last 15 years concerning selected reactions are presented, highlighting the importance of microwave (MW) technology coupled with ionic liquids.

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“…[1,2] Aromatic esters are significant and versatile compounds, known as important ingredients in food, beverages, cosmetics, pharmaceuticals, agrochemicals, detergents and as intermediates for the synthesis of polymers. [2][3][4] So far, palladium complexes are the most studied catalytic systems for alkoxycarbonylation of aryl halides. [5] In addition, the other metals such as nickel, [6,7] cobalt, [8] platinum, [9] rhodium [10] also could be applied as the viable catalysts with the involvement of suitable ligands.…”

Section: Introductionmentioning

confidence: 99%

Efficient and Recyclable RuCl₃ ⋅ 3H₂O Catalyst Modified with Ionic Diphosphine for the Alkoxycarbonylation of Aryl Halides

et al. 2019

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A series of ionic (mono‐/di‐)phosphines (L2, L4, and L6) with structural similarity and their corresponding neutral counterparts (L1, L3, and L5) were applied to modulate the catalytic performance of RuCl3 ⋅ 3H2O. With the involvement of the ionic diphosphine (L4), in which the two phosphino‐fragments were linked by butylene group, RuCl3 ⋅ 3H2O with advantages of low cost, robustness, and good availability was found to be an efficient and recyclable catalyst for the alkoxycarbonylation of aryl halides. The L4‐based RuCl3 ⋅ 3H2O system corresponded to the best conversion of PhI (96 %) along with 99 % selectivity to the target product of methyl benzoate as well as the good generality to alkoxycarbonylation of different aryl halides (ArX, X=I and Br) with alcohols MeOH, EtOH, i‐PrOH and n‐BuOH. The electronic and steric effects of the applied phosphines, which were analyzed by the 31P NMR for 1 J 31 P‐ 77 Se 1 J measurement and single‐crystal X‐ray diffraction, were carefully co‐related to the performance RuCl3 ⋅ 3H2O catalyst. In addition, the L4‐based RuCl3 ⋅ 3H2O system could be recycled successfully for at least eight runs in the ionic liquid [Bmim]PF6.

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Recent improvements in the alkoxycarbonylation reaction catalyzed by transition metal complexes

Cited by 66 publications

References 124 publications

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

Efficient and Recyclable RuCl₃ ⋅ 3H₂O Catalyst Modified with Ionic Diphosphine for the Alkoxycarbonylation of Aryl Halides

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Recent improvements in the alkoxycarbonylation reaction catalyzed by transition metal complexes

Cited by 66 publications

References 124 publications

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: indirect use of carbon dioxide

The Beneficial Sinergy of MW Irradiation and Ionic Liquids in Catalysis of Organic Reactions

Efficient and Recyclable RuCl3 ⋅ 3H2O Catalyst Modified with Ionic Diphosphine for the Alkoxycarbonylation of Aryl Halides

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Product

Resources

About

Efficient and Recyclable RuCl₃ ⋅ 3H₂O Catalyst Modified with Ionic Diphosphine for the Alkoxycarbonylation of Aryl Halides