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Synlett 2018; 29(06): 830-834
DOI: 10.1055/s-0036-1589160
DOI: 10.1055/s-0036-1589160
letter
Direct Iodosulfonylation of Alkylynones with Sulfonylhydrazides and Iodine Pentoxide Leading to Multisubstituted α,β-Enones
This work was supported by the National Natural Science Foundation of China (No. 21302109, 21302110, 21375075, and 21675099), the Natural Science Foundation of Shandong Province (ZR2015JL004 and ZR2016JL012), and the Open Projects Program of the Key Laboratory of Tibetan Medicine Research, Chinese Academy of Sciences, National Training Programs of Innovation and Entrepreneurship for Undergraduates (201610446026).
Further Information
Publication History
Received: 17 October 2017
Accepted after revision: 06 December 2017
Publication Date:
19 January 2018 (online)
§ These authors contributed equally to this work
Abstract
A facile and efficient method has been developed for the construction of multisubstituted α,β-enones through the direct selective iodosulfonylation of alkylynones with sulfonylhydrazides and iodine pentoxide. The present methodology offers a simple and attractive approach to various multisubstituted α,β-enones in moderate to good yields with excellent stereo- and regioselectivities under the metal- and peroxide-free conditions.
Key words
multifunctionalized α,β-enones - iodosulfonylation - alkylynones - sulfonylhydrazides - iodine pentoxideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1589160.
- Supporting Information
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- 15 Preparation of (E)-3-iodo-1,3-diphenyl-2-(phenylsulfonyl)prop-2-en-1-one (4aa): In a 25 mL round-bottomed flack, alkylynone 1a (0.125 mmol), sulfonylhydrazide 2a (0.375 mmol), I2O5 (3; 0.125 mmol), and DME (2 mL) were added. The reaction mixture was stirred at 80 °C for 12 h. After completion the reaction, the solvent was then removed under vacuum. The residue was purified by flash column chromatography using a mixture of petroleum ether and ethyl acetate as eluent to give the desired product 4aa. Yield: 49 mg (83%). 1H NMR (CDCl3, 400 MHz): δ = 8.28 (d, J = 7.2 Hz, 2 H), 7.72 (t, J = 7.3 Hz, 1 H), 7.62 (t, J = 7.8 Hz, 2 H), 7.54 (t, J = 7.4 Hz, 1 H), 7.49 (d, J = 7.3 Hz, 2 H), 7.36–7.26 (m, 5 H), 7.17 (d, J = 6.6 Hz, 2 H); 13C NMR (CDCl3, 100 MHz): δ = 190.6, 149.3, 140.4, 140.0, 134.7, 133.8, 133.7, 130.3, 129.6, 129.3, 129.0, 128.8, 128.3, 128.0, 127.5; HRMS: m/z [M + Na]+ calcd. for C21H15IO3SNa: 496.9684; found: 496.9689.
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