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DOI: 10.1055/a-2586-5753
Direct Alkynylation of Carbonyl Compounds Using an Efficient Catalytic System: Triisopropylsilanol/KOH
This project was supported by the National Natural Science Foundation of China (21202031) and the Natural Science Foundation of Zhejiang Province (Y4110297).
Abstract
The first triisopropylsilanol/KOH-catalyzed direct alkynylation of carbonyl compounds to access propargylic alcohols was achieved. This approach is particularly simple and operates under mild conditions. Moreover, the catalytic system exhibits a wide tolerance for various substrates, including aromatic aldehydes and aromatic acetylenes, giving 1,3-diarylpropargyl alcohols with yields exceeding 88%, avoiding the usual formation of chalcone derivatives or polymers.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2586-2753.
- Supporting Information
Publication History
Received: 08 March 2025
Accepted after revision: 14 April 2025
Accepted Manuscript online:
14 April 2025
Article published online:
28 May 2025
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References and Notes
- 1a Zhang L, Fang G, Kumara RK, Bi X. Synthesis 2015; 47: 2317
- 1b Qian H, Huang D, Bi Y, Yan G. Adv. Synth. Catal. 2019; 361: 3240
- 2a Kobayashi T, Sugitate R, Uchida K, Kawamoto Y, Ito H. Org. Lett. 2024; 26: 1803
- 2b Tanaka K, Kukita K, Ichibakase T, Kotanib S, Nakajima M. Chem. Commun. 2011; 47: 5614
- 2c Chen X, Chen W, Wang L, Yu XQ, Huang DS, Pu L. Tetrahedron 2010; 66: 1990
- 2d Lu G, Li X, Jia X, Chan WL, Chan AS. C. Angew. Chem. Int. Ed. 2003; 42: 5057
- 2e Zhang GW, Meng W, Ma H, Nie J, Zhang WQ, Ma JA. Angew. Chem. Int. Ed. 2011; 50: 3538
- 3a Dhondi PK, Chisholm JD. Org. Lett. 2006; 8: 67
- 3b Zheng Y, Tan Y, Harms K, Marsch M, Riedel R, Zhang L, Meggers E. J. Am. Chem. Soc. 2017; 139: 4322
- 3c Chen JF, Li C. Org. Lett. 2020; 22: 4686
- 3d Sitte NA, Ghiringhelli F, Shevchenko GA, Rominger F, Hashmi AS. K, Schaub T. Adv. Synth. Catal. 2022; 364: 2227
- 3e Takita R, Fukuta Y, Tsuji R, Ohshima T, Shibasaki M. Org. Lett. 2005; 7: 1363
- 3f Wang L, Liu N, Dai B, Ma X, Shi L. RSC Adv. 2015; 5: 10089
- 3g Jia Z, Li X, Chan AS. C, Li CJ. Synlett 2012; 23: 2758
- 4 Ishikawa T, Mizuta T, Hagiwara K, Aikawa T, Kudo T, Saito S. J. Org. Chem. 2003; 68: 3702
- 5 Imahori T, Hori C, Kondo Y. Adv. Synth. Catal. 2004; 346: 1090
- 6 Tzalis D, Knochel P. Angew. Chem. Int. Ed. 1999; 38: 1463
- 7a Babler JH, Liptak VP, Phan N. J. Org. Chem. 1996; 61: 416
- 7b Vashishtha K, Kandula A, Nanubolu JB, Alla M. ChemistrySelect 2023; 8: e202300854
- 8 Dong YW, Wang GW, Wang L. Tetrahedron 2008; 64: 10148
- 9 Tiwari MK, Yadav L, Shyamlal BR. K, Chaudhary S. Asian J. Org. Chem. 2019; 8: 2257
- 10 Weil T, Schreiner PR. Eur. J. Org. Chem. 2005; 2213
- 11 Weil T, Schreiner PR. Tetrahedron Lett. 2012; 53: 2160
- 12 Qi H, Bai Y, Ren Y, Yuan X, Chen S. ChemistrySelect 2023; 8: e202301004
- 13 Soderquist JA, Vaquer J, Diaz MJ, Rane AM, Bordwell FG, Zhang S. Tetrahedron Lett. 1996; 37: 2561
- 14 Dai Y, He Y, Wang Y, Jiang H, Li Z, Chen W. Synthesis 2014; 46: 3041
- 15 Dai Y, Liu Q, Li Z, Chen W, Liu Z. Chin. J. Chem. 2015; 33: 1287