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Synthesis 2021; 53(21): 4079-4085
DOI: 10.1055/a-1542-4258
paper

Synthesis of (Hetero)Aryl-Functionalized Azaindoline Derivatives by Palladium-Catalyzed Domino Heck Cyclization/Hiyama Cross-Coupling

Hao Ye
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
,
Ruotong Zhang
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
,
Xiaolong Xia
b   School of Textile and Clothing, Nantong University, Nantong 226019, P. R. of China
,
Yue Ding
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
c   Anhui Haifeng Analysis and Testing Technology Co. Ltd, Hefei 230000, P. R. of China
,
Meihui Sun
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
c   Anhui Haifeng Analysis and Testing Technology Co. Ltd, Hefei 230000, P. R. of China
,
Lei Shi
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
,
Guomin Jiang
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
,
Xin-Xing Wu∗
a   College of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, P. R. of China
› Author AffiliationsThe generous financial support from the Program of High-Level Talents of Nantong University (03083031) is gratefully acknowledged.
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Abstract

A palladium-catalyzed domino Heck cyclization/Hiyama cross-coupling has been achieved for the synthesis of (hetero)aryl-functionalized azaindoline derivatives bearing all-carbon quaternary centers in 46–85% yields. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and modification of aryl-containing complex bioactive molecules.

Key words

azaindolines - (hetero)arylsilanes - Hiyama coupling - palladium - Heck cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1542-4258.
  • Supporting Information


Publication History

Received: 24 May 2021

Accepted after revision: 01 July 2021

Accepted Manuscript online:
01 July 2021

Article published online:
22 July 2021

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  • References

  • 1 Gonzalez-Lopez De Turiso F, Shin Y, Brown M, Cardozo M, Chen Y, Fong D, Hao X, He X, Henne K, Hu YL, Johnson MG, Kohn T, Lohman J, McBride HJ, McGee LR, Medina JC, Metz D, Miner K, Mohn D, Pattaropong V, Seganish J, Simard JL, Wannberg S, Whittington DA, Yu G, Cushing TD. J. Med. Chem. 2012; 55: 7667
    CrossrefPubMed
    • 2a Grigg R, Loganathan V, Sridharan V, Stevenson P, Sukirthalingam S, Worakun T. Tetrahedron 1996; 52: 11479
      Article in Thieme Connect
    • 2b Grigg R, Mariani E, Sridharan V. Tetrahedron Lett. 2001; 42: 8677
      CrossrefPubMed

      For selected examples, see:
    • 3a Yoon H, Jang YJ, Lautens M. Synthesis 2016; 48: 1483
      CrossrefPubMed
    • 3b Petrone DA, Yoon H, Weinstabl H, Lautens M. Angew. Chem. Int. Ed. 2014; 53: 7908
      CrossrefPubMed
    • 3c Newman SG, Lautens M. J. Am. Chem. Soc. 2011; 133: 1778
      CrossrefPubMed
    • 3d Zhu Q, Lu Y. Angew. Chem. Int. Ed. 2010; 49: 7753
      CrossrefPubMed
    • 3e Leroi C, Bertin D, Dufils PE, Gigmes D, Marque S, Tordo P, Couturier JL, Guerret O, Ciufolini MA. Org. Lett. 2003; 5: 4943
      CrossrefPubMed
    • 3f Yip K.-T, Yang M, Law K.-L, Zhu N.-Y, Yang D. J. Am. Chem. Soc. 2006; 128: 3130
      CrossrefPubMed
    • 3g Larock RC, Babu S. Tetrahedron Lett. 1987; 28: 5291
      Crossref
    • 3h Ju B, Chen S, Kong W. Org. Lett. 2019; 21: 9343
      CrossrefPubMed
    • 3i Liang R.-X, Wang K, Wu Q, Sheng W.-J, Jia Y.-X. Organometallics 2019; 38: 3927
      Crossref
    • 3j Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science 2013; 340: 1065
      CrossrefPubMed
    • 3k Yao T, He D. Org. Lett. 2017; 19: 842
      CrossrefPubMed
    • 3l Wang Y, Yang B, Wu X.-X, Wu Z.-G. Synthesis 2021; 53: 889
      Article in Thieme Connect
    • 3m Liu R.-R, Xu T.-F, Wang Y.-G, Xiang B, Gao J.-R, Jia Y.-X. Chem. Commun. 2016; 52: 13664
      CrossrefPubMed
    • 3n Liu X, Ma X, Huang Y, Gu Z. Org. Lett. 2013; 15: 4814
      CrossrefPubMed
    • 3o Liu X, Li B, Gu Z. J. Org. Chem. 2015; 80: 7547
      CrossrefPubMed
    • 3p Zhou M.-B, Huang X.-C, Liu Y.-Y, Song R.-J, Li J.-H. Chem. Eur. J. 2014; 20: 1843
      CrossrefPubMed
  • 4 Day J, Frederickson M, Hogg C, Johnson C, Meek A, Northern J, Reader M, Reid G. Synlett 2015; 26: 2570
    CrossrefPubMed
  • 5 Schempp DT. T, Daniels BE, Staben ST, Stivala CE. Org. Lett. 2017; 19: 3616
    CrossrefPubMed
  • 6 Wu X.-X, Liu A, Xu S, He J, Sun W, Chen S. Org. Lett. 2018; 20: 1538
    CrossrefPubMed

      • For selected reviews on Hiyama cross-coupling, see:
    • 7a Denmark SE, Sweis RF. Acc. Chem. Res. 2002; 35: 835
      CrossrefPubMed
    • 7b Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
      CrossrefPubMed
    • 7c Komiyama T, Minami Y, Hiyama T. ACS Catal. 2017; 7: 631
      Crossref

      For selected examples and references therein, see:
    • 8a Alacid E, Nájera C. J. Org. Chem. 2008; 73: 2315
      CrossrefPubMed
    • 8b Monguchi Y, Yanase T, Mori S, Sajiki H. Synthesis 2013; 45: 40
    • 8c Gordillo I, de Jesús E, López-Mardomingo C. Org. Lett. 2006; 8: 3517
      CrossrefPubMed
    • 8d Sreedhar B, Kumar AS, Yada D. Synlett 2011; 1081
    • 8e Srimani D, Sawoo S, Sarkar A. Org. Lett. 2007; 9: 3639
      CrossrefPubMed
    • 8f Shi S, Zhang Y. J. Org. Chem. 2007; 72: 5927
      CrossrefPubMed
    • 9a Denmark SE. J. Am. Chem. Soc. 1999; 121: 5821
      Crossref
    • 9b Raders SM, Kingston JV, Verkade JG. J. Org. Chem. 2010; 75: 1744
      CrossrefPubMed
    • 10a Liu Z, Luan N, Shen L, Li J, Zou D, Wu Y, Wu Y. J. Org. Chem. 2019; 84: 12358
      CrossrefPubMed
    • 10b Lee J.-Y, Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
      CrossrefPubMed
    • 10c Jin Y, Wang C. Angew. Chem. Int. Ed. 2019; 58: 6722
      CrossrefPubMed
    • 10d Zhang Z.-M, Xu B, Wu L, Wu Y, Qian Y, Zhou L, Liu Y, Zhang J. Angew. Chem. Int. Ed. 2019; 58: 14653
      CrossrefPubMed
    • 11a Wu X.-X, Ye H, Dai H, Yang B, Wang Y, Chen S, Hu L. Org. Chem. Front. 2020; 7: 2731
      Crossref
    • 11b Wu X.-X, Ye H, Jiang G, Hu L. Org. Biomol. Chem. 2021; 19: 4254
      CrossrefPubMed
    • 11c Wu X.-X, Ye H, Li M, Qian J, Dai H, Shi Y. Org. Chem. Front. 2021; 8: 560
      Crossref
    • 12a Lu M.-Z, Luo H, Hu Z, Shao C, Kan Y, Loh T.-P. Org. Lett. 2020; 22: 9022
      CrossrefPubMed
    • 12b Lu M.-Z, Ding X, Shao C, Hu Z, Luo H, Zhi S, Hui H, Kan Y, Loh T.-P. Org. Lett. 2020; 22: 2663
      CrossrefPubMed