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Synlett 2022; 33(17): 1688-1694
DOI: 10.1055/a-1872-0179
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Versatile OPiv-Supported Organozinc Reagents for Transition-Metal-Catalyzed Cross-Couplings

Xingchen Liu
,
Jixin Wang
,
Jie Li  ∗
Support by the start-up grant (No. GJ10900220) of Soochow University is gratefully acknowledged.
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Dedicated to Prof. Ei-ichi Negishi and Paul Knochel for their brilliant contributions in organic chemistry

Abstract

As one of the most important indispensable tools, organozinc-reagents-based Negishi cross-couplings have been extensively utilized for the synthesis of biologically active molecules and feedstock commodity chemicals. However, the use of air- and moisture-sensitive organozinc halides and expensive palladium catalysis still remain drawbacks. Recently, user-friendly solid OPiv-supported C–Zn, Si–Zn reagents with enhanced air and moisture stability have been prepared, which displayed superior reactivity in various transition-metal-catalyzed cross-couplings, especially in the earth-abundance cobalt and nickel catalysis. Herein, we summarized the recent advances and our research work in the field of the preparation and application of solid organozinc pivalates in the present short review.

1 Introduction

2 Development of Organozinc Pivalates in Two-Component Cross-Couplings

3 Development of Organozinc Pivalates in Three-Component Cross-Couplings

4 Conclusion and Outlook

Key words

organozinc pivalates - silylzinc pivalates - Negishi coupling - alkene difunctionalization - homogeneous catalysis


Publication History

Received: 23 May 2022

Accepted after revision: 09 June 2022

Accepted Manuscript online:
09 June 2022

Article published online:
20 July 2022

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  • References

    • 1a Transition Metals for Organic Synthesis, 2nd ed. . Beller M, Bolm C. Wiley-VCH; Weinheim: 2004
      Google Scholar
    • 1b Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. . de Meijere A, Diederich F. Wiley-VCH; Weinheim: 2004
      Google Scholar
    • 1c Metal-Catalyzed Cross-Coupling Reactions and More . de Meijere A, Bräse S, Oestreich M. Wiley-VCH; Weinheim: 2014
      Google Scholar
    • 3a Negishi E. Angew. Chem. Int. Ed. 2011; 50: 6738
      CrossrefPubMed
    • 3b Haas D, Hammann JM, Greiner R, Knochel P. ACS Catal. 2016; 6: 1540
      Crossref
    • 4a Volochnyuk DM, Gorlova AO, Grygorenko OO. Chem. Eur. J. 2021; 27: 15277
      CrossrefPubMed
    • 4b Devendar P, Qu R.-Y, Kang W.-M, He B, Yang G.-F. J. Agric. Food. Chem. 2018; 66: 8914
      CrossrefPubMed
    • 4c Almond-Thynne J, Blakemore DC, Pryde DC, Spivey AC. Chem. Sci. 2017; 8: 40
      CrossrefPubMed
    • 4d Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
      CrossrefPubMed
  • 5 Bernhardt S, Manolikakes G, Kunz T, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 9205
    CrossrefPubMed
  • 6 Piller FM, Appukkuttan P, Gavryushin A, Helm M, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 6802
    CrossrefPubMed
    • 7a Stathakis CI, Bernhardt S, Quint V, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9428
      CrossrefPubMed
    • 7b Stathakis CI, Manolikakes SM, Knochel P. Org. Lett. 2013; 15: 1302
      CrossrefPubMed
  • 8 Manolikakes SM, Ellwart M, Stathakis CI, Knochel P. Chem. Eur. J. 2014; 20: 12289
    CrossrefPubMed
  • 9 Colombe JR, Bernhardt S, Stathakis C, Buchwald SL, Knochel P. Org. Lett. 2013; 15: 5754
    CrossrefPubMed
  • 10 Greshock TJ, Moore KP, McClain RT, Bellomo A, Chung CK, Dreher SD, Kutchukian PS, Peng Z, Davies IW, Vachal P, Ellwart M, Manolikakes SM, Knochel P, Nantermet PG. Angew. Chem. Int. Ed. 2016; 55: 13714
    CrossrefPubMed
  • 11 Hernán-Gómez A, Herd E, Hevia E, Kennedy AR, Knochel P, Koszinowski K, Manolikakes SM, Mulvey RE, Schnegelsberg C. Angew. Chem. Int. Ed. 2014; 53: 2706
    CrossrefPubMed
    • 12a Lutter FH, Grassl S, Grokenberger L, Hofmayer MS, Chen Y.-H, Knochel P. ChemCatChem 2019; 11: 5188
      CrossrefPubMed
    • 12b Hammann JM, Hofmayer MS, Lutter FH, Thomas L, Knochel P. Synthesis 2017; 49: 3887
      Article in Thieme Connect
    • 12c Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
      CrossrefPubMed
    • 12d Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435
      CrossrefPubMed
  • 13 Hammann JM, Lutter FH, Haas D, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 1082
    CrossrefPubMed
    • 14a Nassar Y, Rodier F, Ferey V, Cossy J. ACS Catal. 2021; 11: 5736
      Crossref
    • 14b Hu Y, Hu B, Liu X, Ren Z, Li J. Org. Biomol. Chem. 2021; 19: 7754
      CrossrefPubMed
  • 15 Li J, Knochel P. Angew. Chem. Int. Ed. 2018; 57: 11436
    CrossrefPubMed
  • 16 Hofmayer MS, Lutter FH, Grokenberger L, Hammann JM, Knochel P. Org. Lett. 2019; 21: 36
    CrossrefPubMed
  • 17 Chen Y.-H, Graβl S, Knochel P. Angew. Chem. Int. Ed. 2018; 57: 1108
    CrossrefPubMed
  • 18 Lutter FH, Grokenberger L, Hofmayer MS, Knochel P. Chem. Sci. 2019; 10: 8241
    CrossrefPubMed
  • 19 Dong Z.-B, Balkenhohl M, Tan E, Knochel P. Org. Lett. 2018; 20: 7581
    CrossrefPubMed
  • 20 Liu X.-G, Zhou C.-J, Lin E, Han X.-L, Zhang S.-S, Li Q, Wang H. Angew. Chem. Int. Ed. 2018; 57: 13096
    CrossrefPubMed
  • 21 Li J, Tan E, Keller N, Chen Y.-H, Zehetmaier PM, Jakowetz AC, Bein T, Knochel P. J. Am. Chem. Soc. 2019; 141: 98
    CrossrefPubMed
  • 22 Ellwart M, Knochel P. Angew. Chem. Int. Ed. 2015; 54: 10662
    CrossrefPubMed
  • 23 Chen Y.-H, Ellwart M, Toupalas G, Ebe Y, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 4612
    CrossrefPubMed
  • 24 Chen Y.-H, Tüllmann CP, Ellwart M, Knochel P. Angew. Chem. Int. Ed. 2017; 56: 9236
    CrossrefPubMed
  • 25 Tüllmann CP, Chen Y.-H, Schuster RJ, Knochel P. Org. Lett. 2018; 20: 4601
    CrossrefPubMed
  • 26 Also see a solid (1H-tetrazol-5-yl)zinc pivalate: Tuellmann CP, Steiner S, Knochel P. Synthesis 2020; 52: 2357
    Article in Thieme Connect

      • Also see the applications of alkynylzinc pivalates in cobalt catalysis:
    • 27a Tomas L, Lutter FH, Hofmayer MS, Karaghiosoff K, Knochel P. Org. Lett. 2018; 20: 2441
      CrossrefPubMed
    • 27b Hammann JM, Thomas L, Chen Y.-H, Haas D, Knochel P. Org. Lett. 2017; 19: 3847
      CrossrefPubMed
    • 29a Orlandi M, Hilton MJ, Yamamoto E, Toste FD, Sigman MS. J. Am. Chem. Soc. 2017; 139: 12688
      CrossrefPubMed
    • 29b Saini V, Sigman MS. J. Am. Chem. Soc. 2012; 134: 11372
      CrossrefPubMed
    • 29c Ikeda Y, Nakamura T, Yorimitsu H, Oshima K. J. Am. Chem. Soc. 2002; 124: 6514
      CrossrefPubMed
    • 30a Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
      CrossrefPubMed
    • 30b O’Hagan D. Chem. Soc. Rev. 2008; 37: 308
      CrossrefPubMed
    • 30c Muller K, Faeh C, Diederich F. Science 2007; 317: 1881
      CrossrefPubMed
  • 31 Cheng X, Liu X, Wang S, Hu Y, Hu B, Lei A, Li J. Nat. Commun. 2021; 12: 4366
    CrossrefPubMed
  • 32 Bähr S, Xue W, Oestreich M. ACS Catal. 2019; 9: 16
    CrossrefPubMed
  • 33 Troegel D, Stohrer J. Coord. Chem. Rev. 2011; 255: 1440
    Crossref
    • 34a Ni D, Brown MK. ACS Catal. 2021; 11: 1858
      CrossrefPubMed
    • 34b Zhao B, Li Y, Li H, Belal M, Zhu L, Yin G. Sci. Bull. 2020; 570
    • 34c Liu Z, Chen J, Lu H.-X, Li X, Gao Y, Coombs JR, Goldfogel MJ, Engle KM. Angew. Chem. Int. Ed. 2019; 58: 17068
      CrossrefPubMed
  • 35 Feng J.-J, Mao W, Zhang L, Oestreich M. Chem. Soc. Rev. 2021; 50: 2010
    CrossrefPubMed
    • 36a Xue W, Shishido R, Oestreich M. Angew. Chem. Int. Ed. 2018; 57: 12141
      CrossrefPubMed
    • 36b Chu CK, Liang Y, Fu GC. J. Am. Chem. Soc. 2016; 138: 6404
      CrossrefPubMed
    • 36c Boebel TA, Hartwig JF. Organometallics 2008; 27: 6013
      CrossrefPubMed
  • 37 Wang J, Duan Z, Liu X, Dong S, Chen K, Li J. Angew. Chem. Int. Ed. 2022; 61: e202202379
    CrossrefPubMed