TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

Hazarika, Debojit; Phukan, Prodeep

doi:10.1016/j.tetlet.2018.11.041

Cited by 8 publications

(3 citation statements)

References 62 publications

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“…Recently N,N- dibromo- p- toluene sulfonamide (TsNBr 2 ) was suggested as an effective reagent for the bromodecarboxylation of α,β-unsaturated carboxylic acids. In the presence of a base, a fast, selective reaction occurred, affording the corresponding bromoalkenes in good to excellent yields The reaction proceeded stereospecifically, forming only E -isomer.…”

Section: Halodecarboxylation Of αβ-Unsaturated Carboxylic Acidsmentioning

confidence: 99%

“…The combination of N,N-dibromo-p-toluene sulfonamide (TsNBr 2 ) with DBU was effective for the bromodecarboxylation of propiolic acids. 331 The reaction instantaneously led to 1-bromoalkynes in good to excellent yields at room temperature (Scheme 141). The utilization of inexpensive and stable trihaloisocyanuric acids as halogenating agents was also explored.…”

Section: Halodecarboxylation Of Acetylenic Carboxylic Acidsmentioning

confidence: 99%

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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%

Section: Halodecarboxylation Of Acetylenic Carboxylic Acidsmentioning

confidence: 99%

Decarboxylative Halogenation of Organic Compounds

2020

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“…From an environmental and practical point of view, stoichiometric halide sources such as NXS or other N -halides may be questionable due to the formation of large amounts of succinimide waste products lowering the atom efficiency of the transformation and complicating product isolation and purification. Therefore, alternative methods for the in situ generation of electrophilic halides have been investigated comprising chemical , or electrochemical halide oxidation methods.…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

Younes

Chen

et al. 2022

ACS Catal.

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In this contribution, we report chemoenzymatic bromodecarboxylation (Hunsdiecker-type) of α,ß-unsaturated carboxylic acids. The extraordinarily robust chloroperoxidase from Curvularia inaequalis ( Ci VCPO) generated hypobromite from H 2 O 2 and bromide, which then spontaneously reacted with a broad range of unsaturated carboxylic acids and yielded the corresponding vinyl bromide products. Selectivity issues arising from the (here undesired) addition of water to the intermediate bromonium ion could be solved by reaction medium engineering. The vinyl bromides so obtained could be used as starting materials for a range of cross-coupling and pericyclic reactions.

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TsNBr₂ Mediated Synthesis of 2‐Acylbenzothiazoles and Quinoxalines from Aryl Methyl Ketones under Metal Free Condition

Loukrakpam

Phukan

2019

ChemistrySelect

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An efficient one pot strategy has been developed for the synthesis of 2-acylbenzothiazoles and quinoxalines from aryl methyl ketones. A variety of heterocycles of these two categories could be prepared in a two-step sequence in excellent yields. The reaction was performed starting from aromatic ketones via an aryl gloxal intermediate which, on further condensation with 2-aminobenzenethiol or o-phenylenediamine, produces the corresponding heterocyclic skeleton. Aromatic ketones are initially treated with TsNBr 2 in DMSO at 65°C for 3 h and the crude reaction mixture was treated with 2-aminobenzenethiol (at 80°C) or o-phenylenediamine (at RT) to generate the final compound.

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TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

Cited by 8 publications

References 62 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

TsNBr₂ Mediated Synthesis of 2‐Acylbenzothiazoles and Quinoxalines from Aryl Methyl Ketones under Metal Free Condition

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TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

Cited by 8 publications

References 62 publications

Decarboxylative Halogenation of Organic Compounds

Decarboxylative Halogenation of Organic Compounds

Chemoenzymatic Hunsdiecker-Type Decarboxylative Bromination of Cinnamic Acids

TsNBr2 Mediated Synthesis of 2‐Acylbenzothiazoles and Quinoxalines from Aryl Methyl Ketones under Metal Free Condition

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TsNBr₂ Mediated Synthesis of 2‐Acylbenzothiazoles and Quinoxalines from Aryl Methyl Ketones under Metal Free Condition