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. 2018 Jul 3;8(42):23919-23923.
doi: 10.1039/c8ra03696a. eCollection 2018 Jun 27.

Synthesis of trifluoromethyl-containing isoindolinones from tertiary enamides via a cascade radical addition and cyclization process

Hui Yu  1 , Mingdong Jiao  1 , Xiaowei Fang  1 , Pengfei Xuan  1
Affiliations

Synthesis of trifluoromethyl-containing isoindolinones from tertiary enamides via a cascade radical addition and cyclization process

Hui Yu et al. RSC Adv. .

Abstract

A radical trifluoromethylation reaction of tertiary enamides was investigated and trifluoromethyl-containing isoindolinones were prepared under mild conditions. Using TMSCF3 as a radical source, PhI(OAc)2 as an oxidant and KHF2 as an additive, tertiary enamides were converted to isoindolinones via a cascade addition and cyclization process in moderate to good yields.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Synthesis of trifluoromethyl-containing isoindolinones.
Scheme 2
Scheme 2. . Results of heterocyclic substrate 5a and 5b.
Scheme 3
Scheme 3. Possible mechanism.
See this image and copyright information in PMC

References

    1. For reviews, see:

    2. Wang J. Sanchez-Rosello M. Acena J. L. del Pozo C. Sorochinsky A. E. Fustero S. Soloshonok V. A. Liu H. Chem. Rev. 2014;114:2432. doi: 10.1021/cr4002879. - DOI - PubMed
    3. Gakh A. A. Shermolovich Y. Curr. Top. Med. Chem. 2014;14:952. doi: 10.2174/1568026614666140202210424. - DOI - PubMed
    1. Zheng Y. Ma J. A. Adv. Synth. Catal. 2010;352:2745. doi: 10.1002/adsc.201000545. - DOI
    2. Studer A. Angew. Chem., Int. Ed. 2012;51:8950. doi: 10.1002/anie.201202624. - DOI - PubMed
    3. Koike T. Akita M. Top. Catal. 2014;57:967. doi: 10.1007/s11244-014-0259-7. - DOI
    4. Honey M. A. Pasceri R. Lewis W. Moody C. J. J. Org. Chem. 2012;77:1396. doi: 10.1021/jo202201w. - DOI - PubMed
    5. Bouillon J. P. Ates C. Janousek Z. Viehe H. G. Tetrahedron Lett. 1993;34:5075. doi: 10.1016/S0040-4039(00)60679-2. - DOI
    1. Yu J. Yang H. Fu H. Adv. Synth. Catal. 2014;356:3669. doi: 10.1002/adsc.201400144. - DOI
    1. Lin J. S. Liu X. G. Zhu X. L. Tan B. Liu X. Y. J. Org. Chem. 2014;79:7084. doi: 10.1021/jo5012619. - DOI - PubMed
    2. Lin J. S. Xiong Y. P. Ma C. L. Zhao L. J. Tan B. Liu X. Y. Chem.–Eur. J. 2014;20:1332. doi: 10.1002/chem.201303387. - DOI - PubMed
    3. Zhang H. Y. Huo W. Ge C. Zhao J. Zhang Y. Synlett. 2017;28:962. doi: 10.1055/s-0036-1588400. - DOI
    1. Xu P. Xie J. Xue Q. Pan C. Cheng Y. Zhu C. Chem.–Eur. J. 2013;19:14039. doi: 10.1002/chem.201302407. - DOI - PubMed
    2. Egami H. Shimizu R. Sodeoka M. J. Fluorine Chem. 2013;152:51. doi: 10.1016/j.jfluchem.2013.03.009. - DOI
    3. An Y. Li Y. Wu J. Org. Chem. Front. 2016;3:570. doi: 10.1039/C6QO00055J. - DOI
    4. Kong W. Casimiro M. Merino E. Nevado C. J. Am. Chem. Soc. 2013;135:14480. doi: 10.1021/ja403954g. - DOI - PubMed
    5. Yang N. Li Z. Ye L. Tan B. Liu X. Y. Chem. Commun. 2016;52:9052–9055. doi: 10.1039/C6CC00364H. - DOI - PubMed