Journal
TETRAHEDRON LETTERS
Volume 52, Issue 16, Pages 1871-1873Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2011.02.029
Keywords
Copper-free click chemistry; Wacker-Tsuji oxidation; Cyclooctanedione; Difluorinated cyclooctyne
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Funding
- Howard Hughes Medical Institute
- US Department of Education
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We report the large-scale synthesis of 1,3-cyclooctanedione in five steps with 29% yield. This molecule is a synthetic precursor to difluorinated cyclooctyne, which participates in a bioorthogonal copper-free click reaction with asides. The final step demonstrates the first successful application of the Wacker-Tsuji oxidation to form a cyclic 1,3-dione. (C) 2011 Elsevier Ltd. All rights reserved.
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