Synlett 2021; 32(15): 1513-1518
DOI: 10.1055/a-1374-9384
cluster
Modern Nickel-Catalyzed Reactions

Visible-Light-Mediated Z-Stereoselective Monoalkylation of β,β-Dichlorostyrenes by Photoredox/Nickel Dual Catalysis

Mehdi Abdellaoui
,
Alexandre Millanvois
,
Etienne Levernier
,
,
The authors thank the Agence Nationale de la Recherche (Grant No. ANR-17-CE07-0018, HyperSilight (PhD grant to EL)), the Centre National de la Recherche Scientifique (CNRS), and Sorbonne Université for financial support.


Abstract

Metal-catalyzed alkylation of 1,1-dihalovinyl moiety commonly suffers from both a lack of stereoselectivity and the overreaction leading to the dialkylation product. The methodology described herein features a new pathway to alkylate stereoselectively β,β-dichlorostyryl substrates to provide the Z-trisubstituted olefin only with fair to good yields. This cross-coupling reaction bears on the smooth and photoinduced formation of a C-centered radical that engages in a nickel-catalyzed organometallic cycle to form the key Csp2–Csp3 bond.

Supporting Information



Publikationsverlauf

Eingereicht: 18. Dezember 2020

Angenommen nach Revision: 26. Januar 2021

Accepted Manuscript online:
27. Januar 2021

Artikel online veröffentlicht:
15. Februar 2021

© 2021. Thieme. All rights reserved

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References and Notes

  • 1 Chelucci G. Chem. Rev. 2012; 112: 1344
  • 2 Arthuis M, Lecup A, Roulland E. Chem. Commun. 2010; 46: 7810
  • 3 Minato A, Suzuki K, Tamao KA. J. Am. Chem. Soc. 1987; 109: 1257
  • 4 Minato A. J. Org. Chem. 1991; 56: 4052
  • 5 Shi J, Zeng X, Negishi E. Org. Lett. 2003; 5: 1825
  • 6 Negishi E, Shi J, Zeng X. Tetrahedron 2005; 61: 9886
  • 7 Andrei D, Wnuk SF. J. Org. Chem. 2006; 71: 405
  • 8 Tan Z, Negishi E. Angew. Chem. Int. Ed. 2006; 45: 762
  • 9 Dos Santos M, Franck X, Hocquemiller R, Figadère B, Peyrat J.-F, Provot O, Brion J.-D, Alami M. Synlett 2004; 2697
  • 10 Liron F, Fosse C, Pernolet A, Roulland E. J. Org. Chem. 2007; 72: 2220
  • 11 DeLano TJ, Reisman SE. ACS Catal. 2019; 9: 6751
  • 12 McAtee RC, McClain EJ, Stephenson CR. J. Trends Chem. 2019; 1: 111
  • 13 Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. Int. Ed. 2018; 57: 10034
  • 14 Crespi S, Fagnoni M. Chem. Rev. 2020; 120: 9790
  • 15 Xuan J, Zang Z.-G, Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 15632
  • 16 Levin MD, Kim S, Toste FD. ACS Cent. Sci. 2016; 2: 293
  • 17 Hopkinson MN, Sahoo B, Li J.-L, Glorius F. Chem. Eur. J. 2014; 20: 3874
  • 18 Nacsa ED, MacMillan DW. C. Org. React. 2019; 471
  • 19 Skubi KL, Blum TR, Yoon TP. Chem. Rev. 2016; 116: 10035
  • 20 Tellis JC, Kelly CB, Primer DN, Jouffroy M, Patel NR, Molander GA. Acc. Chem. Res. 2016; 49: 1429
  • 21 Goddard J.-P, Ollivier C, Fensterbank L. Acc. Chem. Res. 2016; 49: 1924
  • 22 Corcé V, Chamoreau LM, Derat E, Goddard J.-P, Ollivier C, Fensterbank L. Angew. Chem. Int. Ed. 2015; 54: 11414
  • 23 Lévêque C, Chenneberg L, Corcé V, Goddard J.-P, Ollivier C, Fensterbank L. Org. Chem. Front. 2016; 3: 462
  • 24 Jouffroy M, Primer DN, Molander GA. J. Am. Chem. Soc. 2016; 138: 475
  • 25 Patel NR, Kelly CB, Jouffroy M, Molander GA. Org. Lett. 2016; 18: 764
  • 26 Lévêque C, Corcé V, Chenneberg L, Ollivier C, Fensterbank L. Eur. J. Org. Chem. 2017; 2118
  • 27 Levernier E, Corcé V, Rakotoarison L.-M, Smith A, Zhang M, Ognier S, Tatoulian M, Ollivier C, Fensterbank L. Org. Chem. Front. 2019; 6: 1378
  • 28 Lévêque C, Chenneberg L, Corcé V, Ollivier C, Fensterbank L. Chem. Commun. 2016; 52: 9877
  • 29 For a recent access to vinylchlorides, see: Adak T, Hoffmann M, Witzel S, Rudolph M, Dreuw A, Hashmi AS. K. Chem. Eur. J. 2020; 26: 15573
  • 30 Corcé V, Lévêque C, Ollivier C, Fensterbank L. In Science of Synthesis: Photocatalysis in Organic Synthesis . König B. Thieme; Stuttgart: 2019: 427-466
  • 31 Prinsell MR, Everson DA, Weix DJ. Chem. Commun. 2010; 46: 573
  • 32 CCDC 2048159 contains the supplementary crystallographic data for compound 2a-Na. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
  • 33 Holmes RR, Deiters JA. Phosphorus, Sulfur Silicon Relat. Elem. 1995; 98: 105
  • 34 CCDC 2050302 contains the supplementary crystallographic data for compound 2c-Na. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
  • 35 Burton G, Elder JS, Fell SC. M, Stachulski AV. Tetrahedron Lett. 1988; 29: 3003
  • 36 Shang T.-Y, Lu L.-H, Cao Z, Liu Y, He W.-M, Yu B. Chem. Commun. 2019; 55: 5408
  • 37 Le Vaillant F, Garreau M, Nicolai S, Gryn’ova G, Corminboeuf C, Waser J. Chem. Sci. 2018; 9: 5883
  • 38 Tasker SZ, Jamison TF. J. Am. Chem. Soc. 2015; 137: 9531
  • 39 Durandetti M, Nédélec J.-Y, Périchon J. J. Org. Chem. 1996; 61: 1748
  • 40 Weix DJ. Acc. Chem. Res. 2015; 48: 1767
  • 41 Richmond E, Moran J. Synthesis 2018; 50: 499
    • 42a Lévêque C, Ollivier C, Fensterbank L. In Nickel Catalysis in Organic Synthesis . Ogoshi S. Wiley-VCH; Weinheim: 2020: 151-181
    • 42b Goldfogel MJ, Huang L, Weix DJ. In Nickel Catalysis in Organic Synthesis . Ogoshi S. Wiley-VCH; Weinheim: 2020: 183-222
  • 43 Cambié D, Bottecchia C, Straathof NJ. W, Hessel V, Noël T. Chem. Rev. 2016; 116: 10276
  • 44 Garlets ZJ, Nguyen JD, Stephenson CR. J. Isr. J. Chem. 2014; 54: 351