Journal
TETRAHEDRON LETTERS
Volume 87, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2021.153424
Keywords
Furan synthesis; Silyl triflate; One-pot reactions; Cyclizations
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Funding
- American Chemical Society Petroleum Research Fund [55852-UR1]
- Camille & Henry Dreyfus Foundation
- University of Richmond School of Arts Sciences
- University of Richmond Department of Chemistry
- National Science Foundation [CHE-1726291]
- Organic Syntheses
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In the presence of TMSOTf and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans in good yields. The cyclization and desilylation steps appear to be promoted by triflic acid generated in situ from exposure of the reaction mixture to water.
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) and triethylamine, 3-(trimethylsilyl)propargyl carboxylates undergo a one-pot alkylation-cyclization-desilylation reaction with ketones to produce 2-methylfurans. Alkylation at 0 degrees C in methylene chloride, followed by acid-catalyzed cyclization at room temperature, provides the furans in 52-86% yield. Cyclization and desilylation appear to be promoted by triflic acid generated in situ from the exposure of the reaction mixture to water upon completion of the initial substitution reaction. (c) 2021 Elsevier Ltd. All rights reserved.
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