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DOI: 10.1055/a-2068-5625
Conversion of α-Diazoketones into 1-Bromo-2-alkyl- or 2-arylpent-4-en-2-ols using Tin-Mediated Allylation/Propargylation
This research was self-funded by S.K.B., and S.K.B thanks SCC, Habra for providing facilities for this research.
Abstract
High-yielding and mild conditions are used to prepare of 1-bromo-2-alkyl- or 2-arylpent-4-en-2-ols/1-bromo-2-alkyl- or 2-arylpent-4-yn-2-ols from α-diazoketones. The reaction involves allylation/propargylation with successive bromide insertion using in situ generated allyltin bromide/or propargyltin bromide from activated tin metal and allyl/or propargyl bromide.
Key words
tin metal - allylation - propargylation - α-diazoketones - 1-bromo-2-alkyl-ol - 2-arylpent-4-en-2-olPublication History
Received: 02 March 2023
Accepted after revision: 04 April 2023
Accepted Manuscript online:
04 April 2023
Article published online:
08 May 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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- 9 General procedure: (-Diazoketone (1.00 mmol) and allyl bromide/propargyl bromide (1.50 mmol) were dissolved in THF (6.0 mL) at room temperature, then freshly activated tin metal5 (1.20 mmol) was added (Table 1) and the reaction was monitored by TLC. Aqueous saturated ammonium chloride (10.0 mL) was used to quench the reaction, and extraction was performed with ethyl acetate (2 × 10 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. Purification of the crude product by silica gel column chromatography (Merck, 100–200 mesh) using ethyl acetate and hexanes as eluent gave the desired product. 1H and 13C NMR spectra and other analytical data of compounds 3a–i have been reported previously.6,7