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Synlett 2020; 31(11): 1102-1106
DOI: 10.1055/s-0040-1708002
DOI: 10.1055/s-0040-1708002
letter
Acetic Acid Promoted Direct Iodination of Terminal Alkynes with N-Iodosuccinimide: Efficient Preparation of 1-Iodoalkynes
We are grateful to the Hubei Provincial Department of Education (T201719) for generous financial support.Further Information
Publication History
Received: 05 February 2020
Accepted after revision: 02 March 2020
Publication Date:
12 March 2020 (online)
Abstract
An efficient and highly chemoselective approach for the direct iodination of terminal alkynes using acetic acid as N-iodosuccinimide activated reagent under metal-free conditions has been developed. This facile process tolerates a variety of terminal alkynes and provides the desired products in good to excellent yields (up to 99%).
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1708002.
- Supporting Information
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- 12 Iodination of Terminal Alkynes; General Procedure: To a mixture of terminal alkynes (2.0 mmol), acetic acid (2.6 mmol) and 4 Å MS (200 mg) in MeCN (10 mL) was added N-iodosuccinimide (2.2 mmol) and the resulting mixture was heated at 80 °C for 1.5 h. After completion of the reaction, the reaction was quenched with saturated aqueous sodium thiosulfate and the mixture was extracted with ethyl acetate (10 × 3 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel. (Iodoethynyl)benzene (2aa): Prepared according to the general procedure. Purification by column chromatography (petroleum ether) gave 2aa in 91% yield as a pale-yellow oil. 1H NMR (CDCl3, 400 MHz): δ = 7.47–7.44 (m, 2 H), 7.34–7.32 (m, 3 H). 13C NMR (CDCl3, 101 MHz): δ = 132.38, 128.88, 128.32, 123.38, 94.23, 6.74. The overall spectroscopic data are in agreement with assigned structures and consistent with reported data.8c
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