A Green Hunsdiecker Reaction of Cinnamic Acids

Sodré, Leonardo R.; Esteves, Pierre M.; Mattos, Marcio C. S. de

doi:10.5935/0103-5053.20130027

Cited by 10 publications

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“…In this respect, stable and inexpensive trichloro-(TCCA) and tribromoisocyanuric acids (TBCA) constitute an attractive alternative (Scheme 133). 352 Both of these reagents promoted the halodecarboxylation of substituted cinnamic acids to result in 2-bromostyrenes, in satisfactory yields, when tested in the presence of a base in a biphasic medium (diethyl ether-water). Substrates bearing electron-withdrawing groups were not reactive under the reaction conditions.…”

Section: Halodecarboxylation Of αβ-Unsaturatedmentioning

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-Unsaturatedmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

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Addition Reactions: Polar Addition

Kočovský¹

2016

Organic Reaction Mechanisms · 2013

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Metal‐Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

et al. 2017

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2,2,2-Trichloroacetophenone derivatives were synthesized via decarboxylative trichlorination from arylpropiolic acids and trichloroisocyanuric acid (TCCA). Ther eactionw as performed in the presence of water at room temperature,a nd the desired products were obtained in good yields.T he reaction showedg oodf unctional group tolerance towards halide,c yano,n itro,k etone,e ster anda ldehyde groups.I na ddition,t he 2,2,2-trichloroacetophenone derivatives were readily transformed into esters, amides,a nd hydrazides.B asedo ne xperiments with H 2 18 O( water-18 O), we proposedacationic reaction pathwaya st he mechanism and suggested two different pathways for producing aryl-and alkyl-substitutedpropiolic acids.

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A Green Hunsdiecker Reaction of Cinnamic Acids

Cited by 10 publications

References 0 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Addition Reactions: Polar Addition

Metal‐Free Decarboxylative Trichlorination of Alkynyl Carboxylic Acids: Synthesis of Trichloromethyl Ketones

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