Journal
TETRAHEDRON
Volume 68, Issue 5, Pages 1460-1465Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.12.025
Keywords
Click chemistry; Cross-coupling; 12.3-Triazole; TIPS-acetylene; AgF
Categories
Funding
- SRC/ERC [R-11-2007-107-02001-0]
- WCU of National Research Foundation of Korea (NRF) [R32-2008-000-10098-0]
- Korea government (MEST)
- National Research Foundation of Korea [R32-2008-000-10098-0] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3-triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield. (C) 2011 Elsevier Ltd. All rights reserved.
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