Microwave‐Assisted Metal‐Free Decarboxylative Iodination/Bromination of Isoxazole‐4‐carboxylic Acids

Barak, Dinesh S.; Dahatonde, Dipak J.; Batra, Sanjay

doi:10.1002/ajoc.201900572

Cited by 18 publications

(19 citation statements)

References 47 publications

(16 reference statements)

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“…Less electrophilic tetrabutylammonium tribromide [N( n Bu 4 )Br 3 ] was found to be a more suitable reagent for chemospecific decarboxylative bromination [175,176] . Another effective reagent combination for decarboxylative halogenation is the combination of K 3 PO 4 and NXS (X=Br, I), which allows the conversion of 3,5‐disubstituted isoxazole‐4‐carboxylic acids under microwave irradiation [177] …”

Section: Decarboxylative C‐halogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

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Section: Decarboxylative C‐halogen Bond Formationmentioning

confidence: 99%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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“…Saponification of the ester group in 3 ba gave the acid 14 , which via metal‐free decarboxylative halogenation with NIS and NBS in the presence of K 3 PO 4 under microwave irradiation. furnished the halogenated products 15 and 16 in 86 and 91% yields, respectively [27] . In another reaction the methyl sulphide 3 qa was treated with m‐CPBA to access the methylsulphonyl derivative 17 (Scheme 10), which is amenable to further transformations.…”

Section: Resultsmentioning

confidence: 99%

“…furnished the halogenated products 15 and 16 in 86 and 91% yields, respectively. [27] In another reaction the methyl sulphide 3 qa was treated with m-CPBA to access the methylsulphonyl derivative 17 (Scheme 10), which is amenable to further transformations.…”

Section: Resultsmentioning

confidence: 99%

Metal‐ and Photoredox‐Catalyst Free Unified Approach for the Synthesis of Azole‐Fused Quinolines via tert‐Butyl Nitrite‐Mediated Regioselective Annulation

2022

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A metal‐ and photoredox‐catalyst free unified approach for the synthesis of azole‐fused quinolines via annulation reaction between substituted 5/2‐amino‐N‐phenyl azoles and alkynes in the presence of tert‐butyl nitrite (t‐BuONO) in acetonitrile is reported. The reaction that proceeds via radical mechanism afforded solid products, which separated out in the reaction mixture and were isolated by filtration only. The participation of the azole substrate in the reaction ensued only if a functional group capable of accepting hydrogen was present on carbon adjacent to the carbon bearing the amino group. It is anticipated that such functional group facilitated stabilization of the diazoether transition state via hydrogen bonding.

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Section: Additional Miscellaneous Examples Of the Halodecarboxylationmentioning

confidence: 99%

“…The microwave-assisted iodo-and bromodecarboxylation of isoxazole-4-carboxylic acids with halosuccinimides, in the presence of K 3 PO 4 , was recently described by the Batra group (Scheme 86). 299 Both iodo-and bromodecarboxylation were efficient with a broad scope of substrates. Surprisingly, the exceptions were acids bearing the CN substituent on the aromatic ring or the amino or hydrazino group in the isoxazole ring.…”

Section: Additional Miscellaneous Examples Of Thementioning

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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Microwave‐Assisted Metal‐Free Decarboxylative Iodination/Bromination of Isoxazole‐4‐carboxylic Acids

Cited by 18 publications

References 47 publications

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Metal‐ and Photoredox‐Catalyst Free Unified Approach for the Synthesis of Azole‐Fused Quinolines via tert‐Butyl Nitrite‐Mediated Regioselective Annulation

Decarboxylative Halogenation of Organic Compounds

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