RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
PDF herunterladen
Synlett 2025; 36(10): 1408-1412
DOI: 10.1055/a-2527-1554
DOI: 10.1055/a-2527-1554
letter
Improving the Performance of Palladium-Catalyzed Telomerization of 1,3-Butadiene with Malonate by Alcohol Solvent
This work was financially supported by the National Nature Science Foundation of China (22271094), the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB0610000), the Innovation Program of the Shanghai Municipal Education Commission (2023ZKZD37), and the Fundamental Research Funds for the Central Universities.
Abstract
Using alcohol instead of largely excessive malonate as the solvent can improve the performance of palladium-catalyzed telomerization of 1,3-butadiene with malonate. Under the basic conditions, the main reaction was not overwhelmed by the telomerization of 1,3-butadiene with methanol solvent. With this method, methyl (E)-deca-4,9-dienoate, the intermediate for the synthesis of 10-hydroxy decanoic acid, undecanedioic acid, and 11-hydroxy undecanoic acid, can be prepared from the telomerization of 1,3-butadiene with dimethyl malonate in good yield.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2527-1554.
- Supporting Information
Publikationsverlauf
Eingereicht: 15. Januar 2025
Angenommen nach Revision: 28. Januar 2025
Accepted Manuscript online:
28. Januar 2025
Artikel online veröffentlicht:
12. März 2025
© 2025. Thieme. All rights reserved
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Makshina EV, Dusselier M, Janssens W, Degrève J, Jacobs PA, Sels BF. Chem. Soc. Rev. 2014; 43: 7917
- 2 Duan H, Yamada Y, Sato S. Chem. Lett. 2016; 45: 1036
- 3 Behr A, Becker M, Beckmann T, Johnen L, Leschinski J, Reyer S. Angew. Chem. Int. Ed. 2009; 48: 3598
- 4 Herrmann N, Vogelsang D, Behr A, Seidensticker T. ChemCatChem 2018; 10: 5342
- 5 Faßbach TA, Vorholt AJ, Leitner W. ChemCatChem 2019; 11: 1153
- 6 Yang J, Wang P, Neumann H, Jackstell R, Beller M. Ind. Chem. Mater. 2023; 1: 155
- 7 van Leeuwen PW.N.M, Clément ND, Tschan MJ.-L. Coord. Chem. Rev. 2011; 255: 1499
- 8a Behr A, Henze G. Green Chem. 2011; 13: 1
- 8b Inoue Y, Sasaki Y, Hashimoto H. Bull. Chem. Soc. Jpn. 1978; 51: 2375
- 8c Sharif M, Jackstell R, Dastgir S, Al-Shihi B, Beller M. ChemCatChem 2017; 9: 542
- 8d Balbino JM, Dupont J, Bayón JC. ChemCatChem 2018; 10: 206
- 8e Yang Z, Shen C, Dong K. Chin. J. Chem. 2022; 40: 2734
- 9a Tang S, Nozaki K. Acc. Chem. Res. 2022; 55: 1524
- 9b Espinosa LD. G, Williams-Pavlantos K, Turney KM, Wesdemiotis C, Eagan JM. ACS Macro Lett. 2021; 10: 1254
- 9c Liu M, Sun Y, Liang Y, Lin B.-L. ACS Macro Lett. 2017; 6: 1373
- 9d Chen K, Zhu Z, Bai T, Mei Y, Shen T, Ling J, Ni X. Angew. Chem. Int. Ed. 2022; 61: e202213028
- 9e Tang S, Zhao Y, Nozaki K. J. Am. Chem. Soc. 2021; 143: 17953
- 9f Rapagnani RM, Tonks IA. Chem. Commun. 2022; 58: 9586
- 10 Hata G, Takahashi K, Miyake A. J. Org. Chem. 1971; 36: 2116
- 11 Baker R, Winton PM, Turner RW. Tetrahedron Lett. 1980; 21: 1175
- 12 Tsuji J, Masaoka K, Takahashi T. Tetrahedron Lett. 1977; 18: 2267
- 13 Tsuji J, Masaoka K, Takahashi T, Suzuki A, Miyaura N. Bull. Chem. Soc. Jpn. 1977; 50: 2507
- 14a Tolstikov GA, Rozentsvet OA. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1983; 32: 1495
- 14b Tolstikov GA, Rozentsvet OA, Kunakova RV, Novitskaya NN. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1983; 32: 529
- 15 Zhang Q, Song M, Xua Y, Wang W, Wang Z, Zhang L. Prog. Poly. Sci. 2021; 120: 101430
- 16a Jung Y.-S, Joe B.-Y, Seong C.-M, Park N.-S. Synth. Commun. 2001; 31: 2735
- 16b Wang J, Li S, Yang T, Yang J. Tetrahedron 2014; 70: 9029
- 17a Guo J, Fu P, Qiu Z, Chen C, Wang S, Zhang K, Zhang X, Qiao X, Zhao W, Zhao H, Zhao Q, Liu M, Pang X, Cui Z. Compos. Sci. Technol. 2021; 209: 108796
- 17b Liu S, Cui Z, Fu P, Liu M, Zhang L, Li Z, Zhao Q. J. Polym. Sci., Part B: Polym. Phys. 2014; 52: 1094
- 18a Brown HC, Subba Rao BC. J. Am. Chem. Soc. 1956; 78: 5694
- 18b Brown HC, Subba Rao BC. J. Am. Chem. Soc. 1958; 80: 1552
- 18c Brown HC. Tetrahedron 1981; 37: 3547
- 18d Burgess K, Ohlmeyer MJ. Chem. Rev. 1991; 91: 1179
- 19 Huo X, Quan M, Yang G, Zhao X, Liu D, Liu Y, Zhang W. Org. Lett. 2014; 16: 1570
- 20a Jolly PW, Mynott R, Raspel B, Schick KP. Organometallics 1986; 5: 473
- 20b Bruijnincx PC. A, Jastrzebski R, Hausoul PJ. C, Gebbink RJ. M. K, Weckhuysen BM. Pd-Catalyzed Telomerization of 1,3-Dienes with Multifunctional Renewable Substrates: Versatile Routes for the Valorization of Biomass-Derived Platform Molecules. In Organometallics and Renewables. Meier MA. R, Weckhuysen BM, Bruijnincx PC. A. Topics in Organometallic Chemistry 39; Springer; Berlin/Heidelberg: 2019: 45