Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

Liang, Jing; Han, Jie; Wu, Pingjie; Hu, Jian; Hu, Feng; Wu, Fanhong

doi:10.1021/acs.orglett.9b02474

Cited by 25 publications

(17 citation statements)

References 69 publications

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“…The importance of fluorinated ketones has been exemplified by its occurrence in the synthesis of medicinal chemistry drug molecules, [29a] or as catalysts in epoxidation reactions, [29b] and as such, new methods to access these molecules have been generated. One such example was reported by Wu and Wu in 2019, [30] who initially investigated the synthesis of α‐bromo‐α‐fluoroketones 33 (Scheme 7a) employing a procedure first devised by Colby [31] that focused on a trifluoroacetate release/halogenation protocol on α,α‐difluorinated gem ‐diols.…”

Section: Accessing Gem‐difunctionalized Ketones From Carbonyl Substrates and Derivativesmentioning

confidence: 99%

Synthetic Routes Towards the Synthesis of Geminal α‐Difunctionalized Ketones

Day

Vargas

Burtoloso

2021

The Chemical Record

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The importance of gem‐difunctionalized ketones is represented by their broad applications across chemical boundaries over recent years. The interesting reactivities that this class of compounds possess have made them ideal building blocks to access high‐value organic molecules. Furthermore, the gem‐difunctionalized ketone moiety has featured in numerous bioactive molecules. For these reasons, a plethora of routes to access such significant molecules have been developed by research groups worldwide – this account looks at delineating the synthesis of gem‐difunctionalized ketones from carbonyl substrates, diazo compounds, sulfur ylides and alkynyl reactants.

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Section: Accessing Gem‐difunctionalized Ketones From Carbonyl Substrates and Derivativesmentioning

confidence: 99%

Synthetic Routes Towards the Synthesis of Geminal α‐Difunctionalized Ketones

Day

Vargas

Burtoloso

2021

The Chemical Record

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“…In 2009, the research groups of Zou (Table , entry 7) and Zheng (Table , entry 8) introduced a new chlorinating agent, DCDMH (1,3‐dichloro‐5,5‐dimethylhydantoin) for selective and cost‐effective synthesis of α,α‐dichloroketones 1 g and 1 h , respectively. Very recently, Wu and co‐workers, developed a one‐pot protocol for geminal cross dihalogenation reaction of acetophenones 2 i to generate 1 i (Table , entry 9).…”

Section: Synthetic Approaches To αα‐Dihaloketonesmentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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“…[1][2][3][4] Recent examples show that Ni(OTf)2 displays superior catalytic activity compared to other Ni salts in C-H arylation and C-C coupling reactions. 5,6 Fe II or Fe III triflate salts have performed better than other Fe salts in oxidation, radical addition, and C-O bond silylation. [7][8][9] Despite these representative examples and their widespread use in catalysis, there remain challenges associated with the synthesis of metal triflates, which often involves reacting a metal halide with AgOTf.…”

Section: Introductionmentioning

confidence: 99%

On-Demand Electrochemical Synthesis of copper(I) Triflate and Its Application in the Aerobic Oxidation of Alcohols

Nicholls¹,

Bourne²,

Nguyen³

et al. 2021

Preprint

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<p>An on-demand electrochemical synthesis of copper(I) triflate under both batch and continuous flow conditions has been developed. A major benefit of the electrochemical methodology is that the only by-product of the reaction is hydrogen gas which obviates the need for work-up and purification, and water is not incorporated into the product. Upon completion of the electrochemical synthesis, solutions are directly transferred or dispensed into reaction mixtures for the catalytic oxidation of alcohols with no requirement for work-up or purification. </p>

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Nickel-Catalyzed Coupling Reaction of α-Bromo-α-fluoroketones with Arylboronic Acids toward the Synthesis of α-Fluoroketones

Cited by 25 publications

References 69 publications

Synthetic Routes Towards the Synthesis of Geminal α‐Difunctionalized Ketones

Synthetic Routes Towards the Synthesis of Geminal α‐Difunctionalized Ketones

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

On-Demand Electrochemical Synthesis of copper(I) Triflate and Its Application in the Aerobic Oxidation of Alcohols

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