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Wu G, Deng Y, Wu C, et al. Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids. Angew Chem Int Ed Engl. 2014;53(39):10510-4doi: 10.1002/anie.201406765.
Wu, G., Deng, Y., Wu, C., Zhang, Y., & Wang, J. (2014). Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids. Angewandte Chemie (International ed. in English), 53(39), 10510-4. https://doi.org/10.1002/anie.201406765
Wu, Guojiao, et al. "Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids." Angewandte Chemie (International ed. in English) vol. 53,39 (2014): 10510-4. doi: https://doi.org/10.1002/anie.201406765
Wu G, Deng Y, Wu C, Zhang Y, Wang J. Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids. Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10510-4. doi: 10.1002/anie.201406765. Epub 2014 Aug 12. PMID: 25115858.
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Angew Chem Int Ed Engl. 2014 Sep 22;53(39):10510-4. doi: 10.1002/anie.201406765. Epub 2014 Aug 12.

Synthesis of α-aryl esters and nitriles: deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids.

Angewandte Chemie (International ed. in English)

Guojiao Wu, Yifan Deng, Chaoqiang Wu, Yan Zhang, Jianbo Wang

Affiliations

  1. Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871 (China).

PMID: 25115858 DOI: 10.1002/anie.201406765

Abstract

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp(3))-N bonds into C(sp(3))-C(sp(2)) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up.

© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arenes; boron; diazo compounds; nitriles; synthetic methods

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