Journal
TETRAHEDRON
Volume 69, Issue 47, Pages 10022-10029Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.09.059
Keywords
Copper; Aryl halides; Nitriles; Amides; Benzoxazoles
Categories
Funding
- National Natural Science Foundation of China [21202109, 21072140]
- Sichuan Provincial Department of Education [11ZA108]
- Sichuan Normal University [DJ2013-20, DJ2013-21, xyz2013-14-39]
- Sichuan Province Higher Education System Key Laboratory of Advanced Functional Materials [KFKT2013-02]
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An improved protocol for the synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles has been developed. Use of acetaldoxime as the hydrolysis reagent instead of H2O facilitates the operation of the reaction. The significantly decreased amount of nitriles, along with use of weak base K2CO3 instead of strong base KOH, makes this transformation atom-efficient and environmentally benign. A variety of N-arylamides and benzoxazole derivatives can be synthesized according to this approach. (C) 2013 Elsevier Ltd. All rights reserved.
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