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Journal article
Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine
ACS Omega, Vol.4(4), pp.6538-6545
04/30/2019
PMCID: PMC6648761
PMID: 31459785
Web of Science ID: WOS:000466552500050
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.
Details
- Title
- Copper-Catalyzed Electrophilic Chlorocyclization Reaction Using Sodium Chloride as the Source of Electrophilic Chlorine
- Publication Details
- ACS Omega, Vol.4(4), pp.6538-6545
- Resource Type
- Journal article
- Publisher
- American Chemical Society (ACS); United States
- Format
- link
- Number of pages
- 8
- Grant note
- University of West Florida (UWF) 23248 / Research Corporation for Science Advancement for a Cottrell College Science Award Office of Undergraduate Research UWF's Office of Research and Sponsored Programs
- Copyright
- Copyright © 2019 American Chemical Society.
- Identifiers
- WOS:000466552500050; 99380480678006600
- Academic Unit
- Hal Marcus College of Science and Engineering ; Chemistry
- Language
- English