Synthesis 2016; 48(17): 2795-2807
DOI: 10.1055/s-0035-1562342
special topic
© Georg Thieme Verlag Stuttgart · New York

An Indefinitely Air-Stable σ-NiII Precatalyst for Quantitative Cross-Coupling of Unreactive Aryl Halides and Mesylates with Aryl Neopentylglycolboronates

Jagadeesh Malineni
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   eMail: percec@sas.upenn.edu
,
Ryan L. Jezorek
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   eMail: percec@sas.upenn.edu
,
Na Zhang
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   eMail: percec@sas.upenn.edu
,
Virgil Percec*
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA   eMail: percec@sas.upenn.edu
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Publikationsverlauf

Received: 22. April 2016

Accepted after revision: 23. Mai 2016

Publikationsdatum:
28. Juni 2016 (online)


Abstract

Three classes of Ni precatalysts based on π-NiII, π-Ni0 and σ-NiII complexes have been elaborated and employed in different laboratories for the functionalization and cross-coupling of otherwise inert aryl C–O, C–Cl, and C–F electrophiles. Various Ni precatalysts, ligands, boron sources, and reaction conditions that were developed in various research groups, necessitated the selection of the most suitable conditions for desired cross-coupling partners. Here a universal, bench-stable, easily prepared NiIICl(1-naphthyl)(PCy3)2/PCy3 σ-complex, for efficient and quantitative cross-coupling of aryl chlorides, bromides, iodides, mesylates, and fluorides with aryl neopentylglycolboronates is reported. This precatalyst will most probably help to advance the applications of Ni catalysis in organic, supramolecular, and macromolecular synthesis and will provide an easier access to the selection of reaction conditions for various transformations.

Supporting Information

 
  • References

    • 1a Percec V, Bae JY, Hill DH. J. Org. Chem. 1995; 60: 1060
    • 1b Percec V, Bae JY, Hill DH. J. Org. Chem. 1995; 60: 6895
    • 2a Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita A.-M, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
    • 2b Han F.-S. Chem. Soc. Rev. 2013; 42: 5270
    • 2c Mesganaw T, Garg NK. Org. Process Res. Dev. 2013; 17: 29
    • 2d Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299
    • 2e Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
    • 2f Standley EA, Tasker SZ, Jensen KL, Jamison TF. Acc. Chem. Res. 2015; 48: 1503
    • 2g Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
  • 3 Percec V, Golding GM, Smidrkal J, Weichold O. J. Org. Chem. 2004; 69: 3447
    • 4a Percec V, Bae JY, Zhao MY, Hill DH. J. Org. Chem. 1995; 60: 176
    • 4b Percec V, Bae JY, Zhao MY, Hill DH. J. Org. Chem. 1995; 60: 1066
    • 4c Percec V, Okita S, Weiss R. Macromolecules 1992; 25: 1816
    • 4d Percec V, Okita S. J. Polym. Sci. Part A: Polym. Chem. 1993; 31: 877
    • 4e Percec V, Okita S. J. Polym. Sci., Part A: Polym. Chem. 1993; 31: 1087
    • 4f Percec V, Bae JY, Zhao MY, Hill DH. Macromolecules 1995; 28: 6726
    • 4g Grob MC, Feiring AE, Auman BC, Percec V, Zhao MY, Hill DH. Macromolecules 1996; 29: 7284
    • 4h Percec V, Zhao MY, Bae JY, Hill DH. Macromolecules 1996; 29: 3727
    • 4i Percec V, Asandei AD, Hill DH, Crawford D. Macromolecules 1999; 32: 2597
  • 5 Zim D, Lando VR, Dupont J, Monteiro AL. Org. Lett. 2001; 3: 3049
    • 6a Gao H, Li Y, Zhou Y.-G, Han F.-S, Lin Y.-J. Adv. Synth. Catal. 2011; 353: 309
    • 6b Zhao Y.-L, Li Y, Li S.-M, Zhou Y.-G, Sun F.-Y, Gao L.-X, Han F.-S. Adv. Synth. Catal. 2011; 353: 1543
    • 6c Chen G.-J, Han F.-S. Eur. J. Org. Chem. 2012; 3575
  • 7 Rosen BM, Huang C, Percec V. Org. Lett. 2008; 10: 2597
    • 8a Rosen BM, Wilson DA, Wilson CJ, Peterca M, Won BC, Huang C, Lipski LR, Zeng X, Ungar G, Heiney PA, Percec V. J. Am. Chem. Soc. 2009; 131: 17500
    • 8b Percec V, Holerca MN, Nununelin S, Morrison JL, Glodde M, Smidrkal J, Peterca M, Rosen BM, Uchida S, Balagurusamy VS. K, Sienkowska ML, Heiney PA. Chem. Eur. J. 2006; 12: 6216
    • 8c Percec V, Won BC, Peterca M, Heiney PA. J. Am. Chem. Soc. 2007; 129: 11265
    • 9a Quasdorf KW, Tian X, Garg NK. J. Am. Chem. Soc. 2008; 130: 14422
    • 9b Guan B.-T, Wang Y, Li B.-J, Yu D.-G, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
    • 10a Baghbanzadeh M, Pilger C, Kappe CO. J. Org. Chem. 2011; 76: 1507
    • 10b James CA, Coelho AL, Gevaert M, Forgione P, Snieckus V. J. Org. Chem. 2009; 74: 4094
    • 10c Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK. J. Am. Chem. Soc. 2011; 133: 6352
    • 10d Quasdorf KW, Riener M, Petrova KV, Garg NK. J. Am. Chem. Soc. 2009; 131: 17748
  • 11 Chen H, Huang Z, Hu X, Tang G, Xu P, Zhao Y, Cheng C.-H. J. Org. Chem. 2011; 76: 2338
  • 12 Tang ZY, Hu QS. J. Org. Chem. 2006; 71: 2167
  • 13 Leowanawat P, Zhang N, Safi M, Hoffman DJ, Fryberger MC, George A, Percec V. J. Org. Chem. 2012; 77: 2885
  • 14 Tang ZY, Hu QS. J. Am. Chem. Soc. 2004; 126: 3058
  • 15 Standley EA, Jamison TF. J. Am. Chem. Soc. 2013; 135: 1585
  • 16 Wilson DA, Wilson CJ, Rosen BM, Percec V. Org. Lett. 2008; 10: 4879
  • 17 Leowanawat P, Zhang N, Resmerita A.-M, Rosen BM, Percec V. J. Org. Chem. 2011; 76: 9946
  • 18 Zhang N, Hoffman DJ, Gutsche N, Gupta J, Percec V. J. Org. Chem. 2012; 77: 5956
    • 19a Molander GA, Beaumard F. Org. Lett. 2010; 12: 4022
    • 19b Leowanawat P, Zhang N, Percec V. J. Org. Chem. 2012; 77: 1018
  • 20 Tobisu M, Shimasaki T, Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
  • 21 Tobisu M, Xu T, Shimasaki T, Chatani N. J. Am. Chem. Soc. 2011; 133: 19505
  • 22 Hansen AL, Ebran J.-P, Gogsig TM, Skrydstrup T. Chem. Commun. 2006; 4137
    • 23a Harris MR, Hanna LE, Greene MA, Moore CE, Jarvo ER. J. Am. Chem. Soc. 2013; 135: 3303
    • 23b Liu X.-W, Echavarren J, Zarate C, Martin R. J. Am. Chem. Soc. 2015; 137: 12470
  • 24 LaBerge NA, Love JA. Eur. J. Org. Chem. 2015; 5546
  • 25 Niwa T, Ochiai H, Watanabe Y, Hosoya T. J. Am. Chem. Soc. 2015; 137: 14313
  • 26 Álvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17352
    • 27a Cassar L, Ferrara S, Foa M. Adv. Chem. Ser. 1974; 252
    • 27b Vansoolingen J, Verkruijsse HD, Keegstra MA, Brandsma L. Synth. Commun. 1990; 20: 3153
  • 28 Ge S, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 12837
    • 29a Christian AH, Mueller P, Monfette S. Organometallics 2014; 33: 2134
    • 29b Lei X, Obregon KA, Alla J. Appl. Organomet. Chem. 2013; 27: 419
    • 29c Magano J, Monfette S. ACS Catal. 2015; 5: 3120
  • 30 Graham TJ. A, Doyle AG. Org. Lett. 2012; 14: 1616
  • 31 Xing C.-H, Lee J.-R, Tang Z.-Y, Zheng JR, Hu Q.-S. Adv. Synth. Catal. 2011; 353: 2051
  • 32 Chen C, Yang L.-M. J. Org. Chem. 2007; 72: 6324
  • 33 Park NH, Teverovskiy G, Buchwald SL. Org. Lett. 2014; 16: 220
  • 34 Jezorek RL, Zhang N, Leowanawat P, Bunner MH, Gutsche N, Pesti AK. R, Olsen JT, Percec V. Org. Lett. 2014; 16: 6326
  • 35 Schluter AD. J. Polym. Sci., Part A: Polym. Chem. 2001; 39: 1533
  • 36 Foa M, Cassar L. J. Chem. Soc., Dalton Trans. 1975; 2572
  • 37 Cassar L. J. Organomet. Chem. 1973; 54: C57
  • 38 Fan X.-H, Li G, Yang L.-M. J. Organomet. Chem. 2011; 696: 2482
    • 39a Gao C.-Y, Yang L.-M. J. Org. Chem. 2008; 73: 1624
    • 39b Chen C, Yang L.-M. Tetrahedron Lett. 2007; 48: 2427
  • 40 Hu F, Lei X. Tetrahedron 2014; 70: 3854
  • 41 Zheng X, Yang Q, Li Z, Zhu Z, Cui X, Fu H, Chen H, Li R. Catal. Commun. 2014; 57: 143
  • 42 Molander GA, Canturk B. Angew. Chem. Int. Ed. 2009; 48: 9240
    • 43a Leowanawat P, Resmerita A.-M, Moldoveanu C, Liu C, Zhang N, Wilson DA, Hoang LM, Rosen BM, Percec V. J. Org. Chem. 2010; 75: 7822
    • 43b Moldoveanu C, Wilson DA, Wilson CJ, Corcoran P, Rosen BM, Percec V. Org. Lett. 2009; 11: 4974
    • 43c Moldoveanu C, Wilson DA, Wilson CJ, Leowanawat P, Resmerita A.-M, Liu C, Rosen BM, Percec V. J. Org. Chem. 2010; 75: 5438
    • 43d Wilson DA, Wilson CJ, Moldoveanu C, Resmerita A.-M, Corcoran P, Hoang LM, Rosen BM, Percec V. J. Am. Chem. Soc. 2010; 132: 1800
    • 44a Widenhoefer RA, Buchwald SL. Organometallics 1996; 15: 2755
    • 44b Nathel NF. F, Kim J, Hie L, Jiang X, Garg NK. ACS Catal. 2014; 4: 3289
  • 45 Fan X.-H, Yang L.-M. Eur. J. Org. Chem. 2011; 1467