Synthesis of β-aryl vinyl bromides from α, β-unsaturated carboxylic acids by use of ethylenebis(N-methylimidazolium) ditribromide

Hosseinzadeh, Rahman; Tajbakhsh, Mahmood; Mavvaji, Mohammad; Lasemi, Zahra

doi:10.1007/s11164-013-1357-z

Cited by 4 publications

(1 citation statement)

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“…Recently, it was demonstrated that ionic liquids based on imidazolium tribromide could be useful for the bromodecarboxylation of sodium salts of α,β-unsaturated acids. , These brominating agents were used both as solvents and reagents. For instance, stoichiometric amounts of ethylenebis( N -methylimidazolium) ditribromide (EBMIDTB) react with α,β-unsaturated acids in the presence of K 2 CO 3 , to furnish the corresponding vinyl bromide in reasonable yields (Scheme ).…”

Section: Halodecarboxylation Of αβ-Unsaturated Carboxylic Acidsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

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Decarboxylative halogenation, or halodecarboxylation, represents one of the fundamental key methods for the synthesis of ubiquitous organic halides. The method is based on conversion of carboxylic acids to the corresponding organic halides via selective cleavage of a carbon–carbon bond between the skeleton of the molecule and the carboxylic group and the liberation of carbon dioxide. In this review, we discuss and analyze major approaches for the conversion of alkanoic, alkenoic, acetylenic, and (hetero)aromatic acids to the corresponding alkyl, alkenyl, alkynyl, and (hetero)aryl halides. These methods include the preparation of families of valuable organic iodides, bromides, chlorides, and fluorides. The historic and modern methods for halodecarboxylation reactions are broadly discussed, including analysis of their advantages and drawbacks. We critically address the features, reaction selectivity, substrate scopes, and limitations of the approaches. In the available cases, mechanistic details of the reactions are presented, and the generality and uniqueness of the different mechanistic pathways are highlighted. The challenges, opportunities, and future directions in the field of decarboxylative halogenation are provided.

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Section: Halodecarboxylation Of αβ-Unsaturated Carboxylic Acidsmentioning

confidence: 99%