Organofluorine Anesthetics

Reddy, V. Prakash

doi:10.1016/b978-0-444-53748-5.00006-x

Cited by 15 publications

(31 citation statements)

References 44 publications

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“…Next, we were tried to synthesize various halogenated esters which are the very important backbone in pharmaceutically active drug and also in medicinal chemistry. [48,49] Chlorinated ester 6 l were synthesized by carbonylative coupling with iodobenzene as an electrophilic partner in 83% yield. Further, 2, 4 difluorophenyl esters 6 m and 6n were successfully synthesized by carbonylative coupling with corresponding aryl iodide in 80%, 78% yields respectively.…”

Section: Resultsmentioning

confidence: 99%

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

Gaikwad

Bhanage

2019

Applied Organom Chemis

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In this report, we have developed a sustainable protocol for the synthesis of aromatic esters by a carbonylative method using di‐μ‐chlorobis [5‐hydroxy‐2‐[1‐(hydroxyimino‐ĸN) ethyl] phenyl‐ĸC] palladium (II) dimer (1) catalyst in PEG‐400 as a greener and recyclable solvent. The reaction is carried out at room temperature using CO in a balloon. Good to excellent yield of various esters can be synthesize using this protocol. Direct insertion of CO moiety leads to the high atom and step economy. Compared to previous protocol this phosphine free approach for the synthesis of aromatic esters provides high Turnover Number (TON) and Turnover Frequency (TOF). Developed approach has an alternative route for use of conventional palladium precursor with high conversion and selectivity. The catalyst system and product can easily be separated using diethyl ether as a solvent. The Pd/PEG‐400 system could be reused up to a fifth consecutive cycle without any loss of its activity and selectivity.

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Section: Resultsmentioning

confidence: 99%

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

Gaikwad

Bhanage

2019

Applied Organom Chemis

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“…For RA of 18, index I was assumed to be 1. The plot of ΔΔG 0 solv versus I (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) demonstrated satisfactory correlation for 1-14 (Figure 5a).…”

Section: Gas-phase Eas and Ecr Potentials Of 1-15mentioning

confidence: 96%

Electrochemical properties and radical anions of carbocycle-fluorinated quinoxalines and their substituted derivatives

Shundrin

Irtegova

Vasilieva

et al. 2016

J. Phys. Org. Chem.

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Electrochemical reduction (ECR) and oxidation (ECO) of 5,6,7,8‐tetrafluoroquinoxaline (1) and its derivatives bearing various substituents R (7‐H (2), 7,8‐H2 (3), 6‐CF3 (4), 6‐Cl (5), 5,7‐Cl2 (6), 5‐NH2 (7), 6‐OCH3 (8), 6,7‐(OCH3)2 (9), 6,7,8‐(OCH3)3 (10), 5,6,7,8‐(OCH3)4 (11), 6‐OCH3,7‐N(CH3)2 (12), 6‐N(CH3)2 (13), 6,7‐(N(CH3)2)2 (14), 5,6,7‐(N(CH3)2)3 (15), and 7,8‐cyclo‐(=CF‐CF = CF‐CF=) (16)) in the carbocycle have been studied by cyclic voltammetry in MeCN. For 1–4 and 7–15, the first reduction peaks have been found to be 1‐electron and reversible, thus corresponding to the formation of their radical anions (RAs), which are long lived at 295 K except those of 4–6 and 15, 16. Irreversible hydrodechlorination has been observed for 5 and 6 at the first step of their ECR confirmed by EPR detection of corresponding RAs of 2 and 5,7‐H2 derivative of 1 (17) at the next steps. Electrochemically generated RAs of 1–3, 7–14, and 17 have been characterized in MeCN by EPR spectroscopy together with DFT calculations at the (U)B3LYP/6‐31 + G(d) level of theory using PCM to describe the solvent. A noticeable alternation of spin density on the –NCCN– moiety of quinoxaline has been observed for all RAs possessing R‐substitution asymmetry. The comparative electron‐accepting ability of 1–15 has been analyzed in terms of their experimental reduction peak potentials and the (U)B3LYP/6‐31 + G(d)‐calculated gas‐phase first adiabatic electron affinities (EAs). The differences in electron transfer solvation energies for 1–15 have been evaluated on the basis of ECR peaks' potentials and calculated gas‐phase EAs. The ECO of 1–5 and 7–14 has been found to be irreversible.

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“…Because of their unique physical, chemical and biological properties, organic fluorides have found wide use in numerous valuable commercial products and industrial applications. 362 The incorporation of fluorine is a key tool used in the pharmaceutical and agrochemical industries for altering the activity, bioavailability, and metabolic stability of the organic compound. Therefore, reliable and selective methods for the fluorination of organic molecules are highly desirable for discovery of drugs and agrochemicals.…”

Section: The Fluorodecarboxylation Reactionmentioning

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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Organofluorine Anesthetics

Cited by 15 publications

References 44 publications

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

Oxime palladacycle in PEG as a highly efficient and recyclable catalytic system for phenoxycarbonylation of aryl iodides with phenols

Electrochemical properties and radical anions of carbocycle-fluorinated quinoxalines and their substituted derivatives

Decarboxylative Halogenation of Organic Compounds

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