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Liu W, Yang X, Gao Y, et al. Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. J Am Chem Soc. 2017;139(25):8621-8627doi: 10.1021/jacs.7b03538.
Liu, W., Yang, X., Gao, Y., & Li, C. J. (2017). Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. Journal of the American Chemical Society, 139(25), 8621-8627. https://doi.org/10.1021/jacs.7b03538
Liu, Wenbo, et al. "Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature." Journal of the American Chemical Society vol. 139,25 (2017): 8621-8627. doi: https://doi.org/10.1021/jacs.7b03538
Liu W, Yang X, Gao Y, Li CJ. Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature. J Am Chem Soc. 2017 Jun 28;139(25):8621-8627. doi: 10.1021/jacs.7b03538. Epub 2017 Jun 20. PMID: 28578579.
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J Am Chem Soc. 2017 Jun 28;139(25):8621-8627. doi: 10.1021/jacs.7b03538. Epub 2017 Jun 20.

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature.

Journal of the American Chemical Society

Wenbo Liu, Xiaobo Yang, Yang Gao, Chao-Jun Li

Affiliations

  1. Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University , 801 Sherbrooke Street W., Montreal, Quebec H3A 0B8, Canada.
  2. Institute of Catalysis for Energy and Environment, College of Chemistry & Chemical Engineering, Shenyang Normal University , Shenyang, Liaoning 110034, People's Republic of China.

PMID: 28578579 DOI: 10.1021/jacs.7b03538

Abstract

Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.

Publication Types

Grant support