Download PDF
Synthesis 2021; 53(23): 4409-4418
DOI: 10.1055/a-1549-1082
feature

Organophosphane-Catalyzed Construction of Functionalized 2-Ylideneoxindoles via Direct β-Acylation

Wey-Chyng Jeng
,
Po-Chung Chien
,
Sandip Sambhaji Vagh
,
Athukuri Edukondalu
,
Wenwei Lin  ∗
The authors thank the Ministry of Science and Technology, Republic of China (MOST 107-2628-M-003-001-MY3) for financial support.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

We report an efficient method for the direct β-acylation of 2-ylideneoxindoles with acyl chlorides that is catalyzed by organophosphanes in the presence of base. A variety of functionalized 2-ylideneoxindoles were prepared in moderate to good yields under mild, metal-free conditions via a tandem phospha-Michael/O-acylation/intramolecular cyclization/rearrangement sequence. Mechanistic investigations revealed that C–O bond cleavage on a possible betaine intermediate is the key step for the installation of the keto-functionality at the β-position of 2-ylideneoxindoles in a highly stereospecific manner. The synthetic utility of this protocol could also be proven by a scale-up reaction and synthetic transformations of the products.

Key words

β-acylation - functionalized 2-ylideneoxindoles - indolin-3-ones - phospha-Michael addition - phosphine catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1549-1082.
  • Supporting Information


Publication History

Received: 17 June 2021

Accepted after revision: 13 July 2021

Accepted Manuscript online:
13 July 2021

Article published online:
16 August 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Liou Y.-C, Wang H.-W, Edukondalu A, Lin W. Org. Lett. 2021; 23: 3064
      CrossrefPubMed
    • 1b Huang Y, Liao J, Wang W, Liu H, Guo H. Chem. Commun. 2020; 56: 15235
      CrossrefPubMed
    • 1c Li E.-Q, Huang Y. Chem. Commun. 2020; 56: 680
      CrossrefPubMed
    • 1d Guo H, Fan YC, Sun Z, Wu Y, Kwon O. Chem. Rev. 2018; 118: 10049
      CrossrefPubMed
    • 1e Lee C.-J, Chang T.-H, Yu J.-K, Reddy GM, Hsiao M.-Y, Lin W. Org. Lett. 2016; 18: 3758
      CrossrefPubMed
    • 1f Gomez C, Betzer J.-F, Voituriez A, Marinetti A. ChemCatChem 2013; 5: 1055
      Crossref
    • 1g Methot JL, Roush WR. Adv. Synth. Catal. 2004; 346: 1035
      Crossref
    • 1h Lu X, Zhang C, Xu Z. Acc. Chem. Res. 2001; 34: 535
      CrossrefPubMed
    • 2a Nykaza TV, Li G, Yang J, Luzung MR, Radosevich AT. Angew. Chem. Int. Ed. 2020; 59: 4505
      CrossrefPubMed
    • 2b O’Brien CJ, Nixon ZS, Holohan AJ, Kunkel SR, Tellez JL, Doonan BJ, Coyle EE, Lavigne F, Kang LJ, Przeworski KC. Chem. Eur. J. 2013; 19: 15281
      CrossrefPubMed
    • 3a Kim HT, Kang E, Kim M, Joo JM. Org. Lett. 2021; 23: 3657
      CrossrefPubMed
    • 3b Chen X.-Y, Wu Y, Zhou J, Wang P, Yu J.-Q. Org. Lett. 2019; 21: 1426
      CrossrefPubMed
    • 3c Wedi P, van Gemmeren M. Angew. Chem. Int. Ed. 2018; 57: 13016
      CrossrefPubMed
    • 3d Wang P, Verma P, Xia G, Shi J, Qiao JX, Tao S, Cheng PT. W, Poss MA, Farmer ME, Yeung K.-S, Yu J.-Q. Nature 2017; 551: 489
    • 3e Gu Y.-R, Duan X.-H, Yang L, Guo L.-N. Org. Lett. 2017; 19: 5908
      CrossrefPubMed
    • 3f Matcha K, Antonchick AP. Angew. Chem. Int. Ed. 2013; 52: 2082
      CrossrefPubMed
    • 3g Shi Z, Glorius F. Chem. Sci. 2013; 4: 829
      Crossref
    • 3h Fujiwara Y, Domingo V, Seiple IB, Gianatassio R, Del Bel M, Baran PS. J. Am. Chem. Soc. 2011; 133: 3292
      CrossrefPubMed
    • 3i Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
      CrossrefPubMed
    • 4a Grzybowski M, Sadowski B, Butenschön H, Gryko DT. Angew. Chem. Int. Ed. 2020; 59: 2998
      CrossrefPubMed
    • 4b Zhang Y.-F, Shi Z.-J. Acc. Chem. Res. 2019; 52: 161
      CrossrefPubMed
    • 4c Haas D, Hammann JM, Greiner R, Knochel P. ACS Catal. 2016; 6: 1540
      Crossref
    • 4d Sämann C, Schade MA, Yamada S, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 9495
      CrossrefPubMed
    • 4e Wang J, Liu C, Yuan J, Lei A. Angew. Chem. Int. Ed. 2013; 52: 2256
      CrossrefPubMed
    • 4f Johansson Seechurn CC. C, Kitching MO, Colacot TJ, Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
      CrossrefPubMed
    • 4g Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
      CrossrefPubMed
    • 5a Wang C, Wang Z, Xie X, Yao X, Li G, Zu L. Org. Lett. 2017; 19: 1828
      CrossrefPubMed
    • 5b Reddy BN, Ramana CV. Chem. Commun. 2013; 49: 9767
      CrossrefPubMed
    • 5c Higuchi K, Sato Y, Tsuchimochi M, Sugiura K, Hatori M, Kawasaki T. Org. Lett. 2009; 11: 197
      CrossrefPubMed
    • 5d Liu J.-F, Jiang Z.-Y, Wang R.-R, Zheng Y.-T, Chen J.-J, Zhang X.-M, Ma Y.-B. Org. Lett. 2007; 9: 4127
      CrossrefPubMed
    • 5e Pearson WH, Mi Y, Lee IY, Stoy P. J. Am. Chem. Soc. 2001; 123: 6724
      CrossrefPubMed
    • 5f Asai A, Nagamura S, Kobayashi E, Gomi K, Saito H. Bioorg. Med. Chem. Lett. 1996; 6: 1215
      Crossref
    • 6a Liu X, Yan X, Yu J.-H, Tang Y.-D, Wang K, Zhang H. Org. Lett. 2019; 21: 5626
      CrossrefPubMed
    • 6b Li J.-S, Liu Y.-J, Li S, Ma J.-A. Chem. Commun. 2018; 54: 9151
      CrossrefPubMed
    • 6c Li Y.-J, Yan N, Liu C.-H, Yu Y, Zhao Y.-L. Org. Lett. 2017; 19: 1160
      CrossrefPubMed
    • 6d Dalpozzo R. Adv. Synth. Catal. 2017; 359: 1772
      Crossref
    • 6e Parra A, Alfaro R, Marzo L, Moreno-Carrasco A, García Ruano JL, Alemán J. Chem. Commun. 2012; 48: 9759
      CrossrefPubMed
    • 6f Zhang Y.-Q, Zhu D.-Y, Jiao Z.-W, Li B.-S, Zhang F.-M, Tu Y.-Q, Bi Z. Org. Lett. 2011; 13: 3458
      CrossrefPubMed
    • 7a Fei X.-H, Zhao Y.-L, Yang F.-F, Guan X, Li Z.-Q, Wang D.-P, Zhou M, Yang Y.-Y, He B. Adv. Synth. Catal. 2021; 363: 3018
      Crossref
    • 7b Zhou J, Wang B, He X.-H, Liu L, Wu J, Lu J, Peng C, Rao C.-L, Han B. J. Org. Chem. 2019; 84: 5450
      CrossrefPubMed
    • 7c Tang X, Zhu H.-P, Zhou J, Chen Y, Pan X.-L, Guo L, Li J.-L, Peng C, Huang W. Org. Biomol. Chem. 2018; 16: 8169
      CrossrefPubMed
    • 7d Guo C, Schedler M, Daniliuc CG, Glorius F. Angew. Chem. Int. Ed. 2014; 53: 10232
      CrossrefPubMed
    • 7e Wang M, Rong Z.-Q, Zhao Y. Chem. Commun. 2014; 50: 15309
      CrossrefPubMed
    • 8a Edukondalu A, Vagh SS, Lin T.-H, Lin W. Chem. Commun. 2021; 57: 2045
      CrossrefPubMed
    • 8b Vagh SS, Hou B.-J, Edukondalu A, Wang P.-C, Lin W. Org. Lett. 2021; 23: 842
      CrossrefPubMed
    • 8c Khairnar PV, Wu C.-Y, Lin Y.-F, Edukondalu A, Chen Y.-R, Lin W. Org. Lett. 2020; 22: 4760
      CrossrefPubMed
    • 8d Liou Y.-C, Karanam P, Jang Y.-J, Lin W. Org. Lett. 2019; 21: 8008
      CrossrefPubMed
    • 8e Yang S.-M, Wang C.-Y, Lin C.-K, Karanam P, Reddy GM, Tsai Y.-L, Lin W. Angew. Chem. Int. Ed. 2018; 57: 1668
      CrossrefPubMed
    • 8f Chen Y.-R, Reddy GM, Hong S.-H, Wang Y.-Z, Yu J.-K, Lin W. Angew. Chem. Int. Ed. 2017; 56: 5106
      CrossrefPubMed
    • 8g Chang G.-H, Yang M.-C, Möhlmann L, Lin W. Angew. Chem. Int. Ed. 2015; 54: 8502
      CrossrefPubMed
    • 8h Lee C.-J, Jang Y.-J, Wu Z.-Z, Lin W. Org. Lett. 2012; 14: 1906
      CrossrefPubMed
    • 8i Kao T.-T, Syu S.-e, Jhang Y.-W, Lin W. Org. Lett. 2010; 12: 3066
      CrossrefPubMed
    • 9a Khairnar PV, Su Y.-H, Chen Y.-C, Edukondalu A, Chen Y.-R, Lin W. Org. Lett. 2020; 22: 6868
      CrossrefPubMed
    • 9b Liou Y.-C, Su Y.-H, Ku K.-C, Edukondalu A, Lin C.-K, Ke Y.-S, Karanam P, Lee C.-J, Lin W. Org. Lett. 2019; 21: 8339
      CrossrefPubMed
    • 9c Lee C.-J, Sheu C.-N, Tsai C.-C, Wu Z.-Z, Lin W. Chem. Commun. 2014; 50: 5304
      CrossrefPubMed
  • 10 CCDC 2089146 (3aa) and 2086884 (3ab) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
    • 11a Jia H, Dai G, Weng J, Zhang Z, Wang Q, Zhou F, Jiao L, Cui Y, Ren Y, Fan S, Zhou J, Qing W, Gu Y, Wang J, Sai Y, Su W. J. Med. Chem. 2014; 57: 7577
      CrossrefPubMed
    • 11b Reniers J, Meinguet C, Moineaux L, Masereel B, Vincent SP, Frederick R, Wouters J. Eur. J. Med. Chem. 2011; 46: 6104
      CrossrefPubMed
    • 11c Frédérick R, Dumont W, Ooms F, Aschenbach L, Van der Schyf CJ, Castagnoli N, Wouters J, Krief A. J. Med. Chem. 2006; 49: 3743
      CrossrefPubMed
  • 12 Hastings DJ, Weedon AC. Can. J. Chem. 1991; 69: 1171
    Crossref
  • 13 Chien CS, Hasegawa A, Kawasaki T, Sakamoto M. Chem. Pharm. Bull. 1986; 34: 1493
    Crossref