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Synthesis 2022; 54(01): 161-170
DOI: 10.1055/a-1581-2408
DOI: 10.1055/a-1581-2408
paper
p-Toluenesulfonic Acid-Catalyzed Reaction of Phthalaldehydic Acids with Difluoroenoxysilanes: Access to 3-Difluoroalkyl Phthalides
This work was supported by the National Natural Science Foundation of China (NSFC. 21676075).
Abstract
A convenient approach for the synthesis of 3-difluoroalkyl phthalides has been developed from phthalaldehydic acids and difluoroenoxysilanes by using relatively inexpensive p-toluenesulfonic acid monohydrate (PTSA) as a catalyst. A series of 3-difluoroalkyl phthalides and cyclic difluoroalkyl ethers were obtained in up to 99% yield. The products obtained could be readily converted into difluoroalkyl phthalide derivatives by simple modifications.
Key words
p-toluenesulfonic acid monohydrate - catalyst - phthalaldehydic acid - difluoroenoxysilane - 3-difluoroalkyl phthalideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1581-2408.
- Supporting Information
Publication History
Received: 17 June 2021
Accepted after revision: 09 August 2021
Accepted Manuscript online:
09 August 2021
Article published online:
09 September 2021
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References
- 1a Lin G, Chan SS.-K, Chung H.-S, Li S.-L. Stud. Nat. Prod. Chem. 2005; 32: 611
- 1b Beck JJ, Chou S.-C. J. Nat. Prod. 2007; 70: 891
- 1c Teixeira RR, Bressan GC, Pereira WL, Ferreira JG, De Oliveira FM, Thomaz DC. Molecules 2013; 18: 1881
- 1d Karmakar R, Pahari P, Mal D. Chem. Rev. 2014; 114: 6213
- 2a Marco-Contelles J, Zhang Y. J. Med. Chem. 2020; 63: 12485
- 2b Yoganathan K, Rossant C, Ng S, Huang Y, Butler MS, Buss AD. J. Nat. Prod. 2003; 66: 1116
- 2c Othman DI. A, Otsuka K, Takahashi S, Selim KB, El-Sayed MA, Tantawy AS, Okauchi T, Kitamura M. Synlett 2018; 29: 457
- 2d Gentry EJ, Jampani HB, Keshavarz-Shokri A, Morton MD, Vander VeldeD, Telikepalli H, Mitscher LA, Shawar R, Humble D, Baker W. J. Nat. Prod. 1998; 61: 1187
- 3a Yuan S, Zhang DQ, Zhang JY, Yu B, LiuH M. Org. Lett. 2020; 22: 814
- 3b Liang X, Xiong MT, Zhu HP, Shi KQ, Zhou YF, Pan YJ. Org. Lett. 2020; 22: 9568
- 3c Chen WK, Li J, Xie H, Wang J. Org. Lett. 2020; 22: 3586
- 3d Iwasaki M, Kazao Y, Ishida T, Nishihara Y. Org. Lett. 2020; 22: 7343
- 3e Pan Y.-L, Zheng H.-L, Wang J, Yang C, Li X, Cheng J.-P. ACS Catal. 2020; 10: 8069
- 3f Liu Y, Majhi PK, Song R, Mou C, Hao L, Chai H, Jin Z, Chi YR. Angew. Chem. Int. Ed. 2020; 59: 3859
- 4a Ma J.-A, Cahard D. Chem. Rev. 2004; 104: 6119
- 4b O’Hagan D. Chem. Soc. Rev. 2008; 37: 308
- 4c Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
- 5a Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
- 5b Meanwell NA. J. Med. Chem. 2018; 61: 5822
- 5c Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
- 6a Ni C, Zhu L, Hu J. Huaxue Xuebao 2015; 73: 90
- 6b Feng Z, Xiao Y.-L, Zhang X. Acc. Chem. Res. 2018; 51: 2264
- 6c Dong D.-Q, Yang H, Shi J.-L, Si W.-J, Wang Z.-L, Xu X.-M. Org. Chem. Front. 2020; 7: 2538
- 7a Sha W, Zhang W, Ni S, Mei H, Han J, Pan Y. J. Org. Chem. 2017; 82: 9824
- 7b Da Y, Han S, Du X, Liu S, Liu L, Li J. Org. Lett. 2018; 20: 5149
- 7c Yuan F, Zhou S, Yang Y, Guo M, Tang X, Wang G. Org. Chem. Front. 2018; 5: 3306
- 7d Yang Q, Lin Q, Xing H, Zhao Z. Org. Chem. Front. 2019; 6: 3939
- 8 Inaba M, Sakai T, Shinada S, Sugiishi T, Nishina Y, Shibata N, Amii H. Beilstein J. Org. Chem. 2018; 14: 182
- 9a Decostanzi M, Campagne J.-M, Leclerc E. Org. Biomol. Chem. 2015; 13: 7351
- 9b Hu X.-S, Yu J.-S, Zhou J. Chem. Commun. 2019; 55: 13638
- 9c Li J.-S, Liu Y.-J, Zhang G.-W, Ma J.-A. Org. Lett. 2017; 19: 6364
- 9d Gao X, Cheng R, Xiao Y.-L, Wan X.-L, Zhang X. Chem 2019; 5: 2987
- 9e Li J, Chen Y, Zhong R, Zhang Y, Yang J, Ding H, Wang Z. Org. Lett. 2020; 22: 1164
- 9f Hao Y.-J, Gong Y, Zhou Y, Zhou J, Yu J.-S. Org. Lett. 2020; 22: 8516
- 9g Rong M.-Y, Li J.-S, Zhou Y, Zhang F.-G, Ma J.-A. Org. Lett. 2020; 22: 9010
- 9h Huang X, Zhang Y.-G, Liang W.-J, Zhang Q.-F, Zhan Y.-L, Kong L.-C, Peng B. Chem. Sci. 2020; 11: 3048
- 9i Li J, Xi W, Zhong R, Yang J, Wang L, Ding H, Wang Z. Chem. Commun. 2021; 57: 1050
- 10a Chorki F, Grellepois F, Crousse B, Ourévitch M, Bonnet-Delpon D, Bégué J.-P. J. Org. Chem. 2001; 66: 7858
- 10b Yu J.-S, Liu Y.-L, Tang J, Wang X, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 9512
- 10c Wu Y.-B, Wan L, Lu G.-P, Cai C. Eur. J. Org. Chem. 2017; 3438
- 10d Chen T, Cai C. New J. Chem. 2017; 41: 2519
- 11a Fu M.-L, Liu J.-B, Xu X.-H, Qing F.-L. J. Org. Chem. 2017; 82: 3702
- 11b Tian Y.-P, Gong Y, Hu X.-S, Yu J.-S, Zhou Y, Zhou J. Org. Biomol. Chem. 2019; 17: 9430
- 12a Wheeler DD, Young DC, Erley DS. J. Org. Chem. 1957; 22: 547
- 12b da Silva Maia AF, Siqueira RP, de Oliveira FM, Ferreira JG, da Silva SF, Caiuby CA. D, de Oliveira LL, de Paula SO, Souza RA. C, Guilardi S, Bressan GC, Teixeira RR. Bioorg. Med. Chem. Lett. 2016; 26: 2810
- 13a Zhang H, Zhang S, Liu L, Luo G, Duan W, Wang W. J. Org. Chem. 2010; 75: 368
- 13b Jia L, Han F. Beilstein J. Org. Chem. 2017; 13: 1425
- 14a Liu C, Kudo K, Hashimoto Y, Saigo K. J. Org. Chem. 1996; 61: 494
- 14b Yamamoto Y, Ota M, Kodama S, Michimoto K, Nomoto A, Ogawa A, Furuya M, Kawakami K. ACS Omega 2021; 6: 2239
For selected recent examples, see:
For selected reviews, see:
For reviews on difluoroenoxysilanes see:
For selected recent examples, see:
For examples of the reaction of difluoroenoxysilanes with aldehydes, see:
For selected examples on the synthesis of fluoroalkyl ethers, see: