Three-Component One-Pot Synthesis of Unsymmetrical Diarylalkynes by Thermocontrolled Sequential Sonogashira Reactions Using Potassium Ethynyltrifluoroborate
- Three-Component One-Pot Synthesis of Unsymmetrical Diarylalkynes by Thermocontrolled Sequential Sonogashira Reactions Using Potassium Ethynyltrifluoroborate
- 최재영; 함정엽; 김태정; 김영석; 노태섭; 정규혁
- Alkynes; Borates; C-C coupling; Cross-coupling; Multicomponent reactions
- Issue Date
- European journal of organic chemistry
- VOL 2017, NO 17-2431
- Unsymmetrical diarylalkynes were synthesized in moderate to good yields through a three-component one-pot procedure involving thermocontrolled sequential Sonogashira reactions with potassium ethynyltrifluoroborate and two different reactive aryl halides. The one-pot procedure was initiated by the palladium/copper-catalyzed Sonogashira coupling of potassium ethynyltrifluoroborate to an aryl iodide or electron-deficient aryl bromide at 40 °C. Following a subsequent deboronative Sonogashira reaction of the in situ generated potassium (arylethynyl)trifluoroborate, a second coupling to a lessactive electron-rich aryl bromide at 80 °C, without any additional palladium/copper catalyst or base, gave rise to unsymmetrical diarylalkynes.
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