Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2

Zhang, Xiao; Zhang, Wenzhen; Shi, Ling‐Long; Zhu, Chuang; Jiang, Jiao‐Lai; Lu, Xiao‐Bing

doi:10.1016/j.tet.2012.08.053

Cited by 41 publications

(20 citation statements)

References 72 publications

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“…Cs 2 CO 3 functioned with dual roles: as a base abstracting hydrogen from the terminal alkyne and a crucial player in generating the catalytically active species 6-1. 30 Recently, He et al discovered Ag 2 WO 4 to be an efficient Ag(I)-based bifunctional catalyst for improving the reaction under atmospheric CO 2 at room temperature. 28 2-Alkynoates 9 could be obtained with high efficiency through a ligand-free AgI-catalysed three-component reaction of aryl-and alkyl-substituted terminal alkynes, CO 2 , and various a-functionalized chloromethanes 8 such as allylic, propargylic and benzylic chlorides.…”

Section: Alkynylationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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Silver is a less expensive noble metal. Superior alkynophilicity due to π-coordination with the carbon-carbon triple bond makes silver salts ideal catalysts for alkyne-based organic reactions. This review highlights the progress in alkyne chemistry via silver catalysis primarily over the past five years (ca. 2010-2014). The discussion is developed in terms of the bond type formed with the acetylenic carbon (i.e., C-C, C-N, C-O, C-Halo, C-P and C-B). Compared with other coinage metals such as Au and Cu, silver catalysis is frequently observed to be unique. This critical review clearly indicates that silver catalysis provides a significant impetus to the rapid evolution of alkyne-based organic reactions, such as alkynylation, hydrofunctionalization, cycloaddition, cycloisomerization, and cascade reactions.

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Section: Alkynylationmentioning

confidence: 99%

Silver-catalysed reactions of alkynes: recent advances

2015

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“…The process was extended to the carboxylative alkylation methodology using alkyl chlorides and the same catalyst at low loading (0.1 mol%) [104]. In comparison to the previous carboxylation procedure, an increase of the CO 2 pressure to 15 bar was required.…”

Section: Silver-catalyzed Reactionsmentioning

confidence: 99%

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Brill

Lazreg

Cazin

et al. 2015

Topics in Organometallic Chemistry

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The development of sustainable chemical processes is a long-standing challenge. Carbon dioxide represents a renewable C1 building block for organic synthesis and industrial applications as an alternative to other common feedstocks which are based on natural gas, petroleum oil, or coal. Apart from the advantages associated with the nontoxicity and abundance of CO 2 , its utilization further enables the reduction in its atmospheric content, which contributes significantly to the greenhouse effect. Although widespread application of CO 2 in organic synthesis -even on an industrial scale -will not be able to fully compensate for the steadily increasing atmospheric quantities produced (mainly by the combustion of fuels), ecological and economical factors make its usage highly desirable. Therefore, tremendous efforts toward activation and utilization of CO 2 have been made by the scientific community over the last 30 years, and, as a result, the number of highly efficient transition metal-catalyzed CO 2 -incorporative reactions has increased dramatically, especially within the last decade. The achievements in the development of sustainable and economic chemical processes for the carboxylation of organic molecules with CO 2 are presented in detail in this chapter.

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“…Lu's group then advanced the copper-catalyzed protocol to a more convenient silver-catalyzed approach with low catalyst loading, which could prepare a wide range of propiolic acid esters in the same way but dispensing with addition of ligand and high pressure of CO 2 . 65,66 A polyNHCs/copper catalytic system has been exploited by Zhang and co-workers. 67 Alkynes were successfully converted to propiolic acids via C-H bond activation and carboxylation with or without external base.…”

Section: Reaction Of Monoynes With Comentioning

confidence: 99%

Catalytic conversion of carbon dioxide to carboxylic acid derivatives

Liu

2014

Greenhouse Gases

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Chemical utilization of the greenhouse gas, i.e., CO 2 as an abundant, easily available, and renewable carbon feedstock for producing chemicals, materials, and fuels is attractive as an integral part of the carbon cycle. Based on the principle of CO 2 activation and elaborately designed catalysts, various transformation of CO 2 can be realized under mild conditions. In particular, establishing practical methodologies for catalytic carboxylation by CO 2 as carboxylative reagent would be a fascinating dream for synthetic chemists. This review covers the updated advances in the catalytic conversion of CO 2 into carboxylic acid derivatives from alkenes, alkynes, aromatic halides, aromatic C(sp 2 )-H bonds, etc.

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Ligand-free Ag(I)-catalyzed carboxylative coupling of terminal alkynes, chloride compounds, and CO2

Cited by 41 publications

References 72 publications

Silver-catalysed reactions of alkynes: recent advances

Silver-catalysed reactions of alkynes: recent advances

Transition Metal-Catalyzed Carboxylation of Organic Substrates with Carbon Dioxide

Catalytic conversion of carbon dioxide to carboxylic acid derivatives

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