Dataset Information

Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine.

ABSTRACT: The synthesis of 2,3-disubstituted benzo[b]thiophenes with selective placement of a chlorine moiety at the 3 position while maintaining diversity at the 2 position has only been accomplished by a handful of conditions in the past. The development of a greener, less expensive, and simpler method is paramount for the exploration of innovative compounds for application in medicinal and materials chemistry. Herein, the first reported copper-catalyzed electrophilic chlorocyclization method was developed and employed across diverse substrates to generate highly functionalized 2,3-disubstituted benzo[b]thiophenes and 2,3,5-trisubstituted thiophenes in very high yields. This method was optimized in both ethanol and acetonitrile in a comparative solvent study. The utility of this method was further expanded beyond chlorocyclization by changing the sodium halide to generate bromo- and iodocyclization products in excellent yields.

SUBMITTER: Walter C

PROVIDER: S-EPMC6648761 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine.

Walter Christopher C Fallows Natalie N Kesharwani Tanay T

ACS omega 20190409 4

The synthesis of 2,3-disubstituted benzo[<i>b</i>]thiophenes with selective placement of a chlorine moiety at the 3 position while maintaining diversity at the 2 position has only been accomplished by a handful of conditions in the past. The development of a greener, less expensive, and simpler method is paramount for the exploration of innovative compounds for application in medicinal and materials chemistry. Herein, the first reported copper-catalyzed electrophilic chlorocyclization method was ...[more]

PMID: 31459785

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Project description:Building water systems promote the regrowth and survival of opportunistic pathogens, such as Legionella pneumophila, especially within biofilms, where most drinking water microbes reside. However, compared to their planktonic form, disinfection efficacy for the biofilm-associated forms of water-based pathogens is unclear. The aim of this study was to determine the effectiveness of free chlorine and monochloramine in the inactivation of biofilm-associated L. pneumophila strain Philadelphia-1 serogroup 1 (LpP1s1). Mature (1.5- to 2-year-old) drinking water biofilms were developed on copper (Cu) and polyvinyl chloride (PVC) slides within biofilm annular reactors, then colonized with LpP1s1 at approximately 4 log10 CFU cm-2 and exposed to 2 mg liter-1 of free chlorine or monochloramine. Ct (disinfectant concentration × time, expressed as mg min liter-1) inactivation values for 2-, 3-, and 4-log10 reductions of planktonic and biofilm LpP1s1 were determined. For planktonic LpP1s1, free chlorine was more effective at inactivation than was monochloramine treatment, and for biofilm-associated LpP1s1, monochloramine was more effective on Cu biofilms while free chlorine was more effective on PVC biofilms. In contrast to monochloramine, free chlorine treatment of Cu and PVC biofilms, negatively impacted LpP1s1 16S rRNA gene transcript levels and may act synergistically with Cu surfaces to further reduce transcript levels. Moreover, LpP1s1 cells shed from biofilms into the bulk water were more resistant to disinfection than were prepared planktonic LpP1s1 cells. Results from this study indicate that biofilm association, disinfectant type, and substratum play an important role in the survival of Legionella pneumophila in building water systems.IMPORTANCE Microbial regrowth within building water systems are promoted by water stagnation, low disinfectant residual, high surface-to-volume ratio, amenable growth temperatures, and colonization of drinking water biofilms. Moreover, biofilms provide protection from environmental stresses, access to higher levels of nutrients, and opportunities for symbiotic interactions with other microbes. Disinfectant efficacy information is historically based on inactivation of pathogens in their planktonic, free-floating forms. However, due to the ecological importance of drinking water biofilms for pathogen survival, this study evaluated the efficacy of two common disinfectants, free chlorine and monochloramine, on Legionella pneumophila colonizing mature, drinking water biofilms established on copper and PVC surfaces. Results showed that inactivation was dependent on the disinfectant type and biofilm substratum. Overall, this, and other related research, will provide a better understanding of Legionella ecological stability and survival and aid policy makers in the management of exposure risks to water-based pathogens within building water systems.

Dataset Information

Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine.

Publications

Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine.

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