Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

Jayaraman, Aravindan; Lee, Sunwoo

doi:10.1021/acs.orglett.9b00597

Cited by 17 publications

(11 citation statements)

References 43 publications

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“…In addition, we have also developed a decarboxylative halogenation reaction of alkynoic acids . Very recently, we reported that 1-fluoro-2,2-diiodovinylarenes can be obtained upon reacting alkynoic acid with Py·HF and 1,3-diiodo-5,5-dimethylhydantoin ( DIH) in the presence of a catalytic amount of AgOAc . 1-Fluoro-2,2-diiodovinylarenes are gem -diiodo-substituted alkenes that can react with a variety of nucleophiles via transition-metal-catalyzed coupling reactions.…”

mentioning

confidence: 99%

Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions

Jayaraman

Lee

2019

Org. Lett.

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Palladium-catalyzed decarboxylative coupling reactions using alkynoic acids and 1-fluoro-2,2-diiodovinylarenes provide mono- and dialkynylfluoroalkenes with high selectivity. When the reaction was conducted using DBU/DMSO, the hydrodeiodinated monoalkynylfluoroalkene product was formed, whereas performing the reaction using Et3N/THF gave the dialkynylfluoroalkene product. Both reaction conditions gave high yields of the desired enyne and endiyne products bearing fluorine atoms.

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confidence: 99%

Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions

Jayaraman

Lee

2019

Org. Lett.

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“…Thus, iodophenyl acetylene was prepared from propiolic acid and DIH, in a 91% isolated yield (Scheme 147). 361 Interestingly, when such an iododecarboxylation was performed in the presence of a fluorine source, 2,2-diiodo-1fluoro-alkenes were isolated as the reaction products (Scheme 148a).…”

Section: Halodecarboxylation Of Acetylenic 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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“…Following this concept, we successfully obtained 2-fluoro-1,1-diiodoalkenes from the reaction of alkynoic acids with HF•pyridine and 1,3-diiodo-5,5-dimethylhydantoin (DIH) at room temperature in the presence of catalytic AgOAc (Scheme 57). 66 Aryl-and alkyl-substituted propynoic acids provided the desired 2-fluoro-1,1-diiodoalkenes in moderate yields and functional group tolerance. These 2-fluoro-1,1-diiodoalkenes were employed in Pd-catalyzed crosscoupling reactions, such as the Suzuki and Hiyama, and decarboxylative coupling reactions.…”

Section: Fluorodiiodinationmentioning

confidence: 99%

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

Idris

Lee

2020

Synthesis

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Alkynoic acids have been widely employed as alkyne and alkene sources in decarboxylative reactions. Alkynoic acid coupling leads to the formation of direct coupling products and cyclized products through sequential reactions. Moreover, homocoupling and multicomponent reactions have been developed. The decarboxylative addition of alkynoic acids generates the corresponding alkene products. A number of synthetic methods are utilized for the preparation of arylpropynoic acids including the Sonogashira coupling and the carboxylation of terminal alkynes. Recently, the use of decarboxylative halogenations has also been reported. This review covers decarboxylative reactions of alkynoic acids reported between 2013 and 2019; further, it is divided into several sections according to the type of reaction.1 Introduction2 Direct Coupling3 Sequential Reactions4 Homocoupling5 Multicomponent Reactions6 Addition7 Halogenations8 Synthesis of Alkynoic Acids9 Conclusion

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Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

Cited by 17 publications

References 43 publications

Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions

Selective Mono- and Dialkynylation of 1-Fluoro-2,2-diiodovinylarenes Using Pd-Catalyzed Decarboxylative Coupling Reactions

Decarboxylative Halogenation of Organic Compounds

Recent Advances in Decarboxylative Reactions of Alkynoic Acids

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