Log in

Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

Abstract

The traditional transition metal-catalyzed cross-coupling reaction, although well suited for C(sp2)–C(sp2) cross-coupling, has proven less amenable toward coupling of C(sp3)-hybridized centers, particularly using functional group tolerant reagents and reaction conditions. The development of photoredox/Ni dual catalytic methods for cross-coupling has opened new vistas for the construction of carbon–carbon bonds at C(sp3)-hybridized centers. In this chapter, a general outline of the features of such processes is detailed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price includes VAT (Brazil)

Instant access to the full article PDF.

Scheme 1
Scheme 2
Scheme 3
Scheme 4
Scheme 5
Scheme 6
Scheme 7
Scheme 8
Scheme 9
Scheme 10
Scheme 11
Scheme 12
Scheme 13
Scheme 14
Scheme 15
Scheme 16
Scheme 17
Scheme 18
Scheme 19
Scheme 20
Scheme 21
Scheme 22
Scheme 23
Scheme 24
Scheme 25
Scheme 26
Scheme 27
Scheme 28
Scheme 29
Scheme 30
Scheme 31
Scheme 32
Scheme 33
Scheme 34
Scheme 35
Scheme 36
Scheme 37
Scheme 38
Scheme 39
Scheme 40

Similar content being viewed by others

References

  1. Molander GA (2013) (ed) Science of synthesis cross-coupling and Heck-type reactions: C-C cross-coupling using organometallic partners. Thieme, Stuttgart

  2. Nicolaou KC, Bulger PG, Sarlah D (2005) Angew Chem Int Ed 44:4442

    Article  CAS  Google Scholar 

  3. Seechurn CCCJ, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062

    Article  Google Scholar 

  4. González-Bobes F, Fu GC (2006) J Am Chem Soc 128:5360

    Article  Google Scholar 

  5. Krasovskiy AL, Haley S, Voigtritter K, Lipshutz BH (2014) Org Lett 16:4066

    Article  CAS  Google Scholar 

  6. Yang Y, Niedermann K, Han C, Buchwald SL (2014) Org Lett 16:4638

    Article  CAS  Google Scholar 

  7. Jiang X, Gandelman M (2015) J Am Chem Soc 137:2542

    Article  CAS  Google Scholar 

  8. St. Denis JD, Scully CCG, Lee CF, Yudin AK (2014) Org Lett 16:1338

    Article  CAS  Google Scholar 

  9. Gutierrez O, Tellis JC, Primer DN, Molander GA, Kozlowski MC (2015) J Am Chem Soc 137:4896

    Article  CAS  Google Scholar 

  10. Lennox AJJ, Lloyd-Jones GC (2014) Chem Soc Rev 43:412

    Article  CAS  Google Scholar 

  11. Molander GA, Ribagorda M (2003) J Am Chem Soc 125:11148

    Article  CAS  Google Scholar 

  12. Molander GA, Figueroa R (2006) Org Lett 8:75

    Article  CAS  Google Scholar 

  13. Molander GA, Petrillo DE (2006) J Am Chem Soc 128:9634

    Article  CAS  Google Scholar 

  14. Dreher SD, Dormer PG, Sandrock DL, Molander GA (2008) J Am Chem Soc 130:9257

    Article  CAS  Google Scholar 

  15. Dreher SD, Lim S-E, Sandrock DL, Molander GA (2009) J Org Chem 74:3626

    Article  CAS  Google Scholar 

  16. Li L, Zhao S, Joshi-Pangu A, Diane M, Biscoe MR (2014) J Am Chem Soc 136:14027

    Article  CAS  Google Scholar 

  17. Tellis JC, Primer DN, Molander GA (2014) Science 345:433

    Article  CAS  Google Scholar 

  18. Primer DN, Karakaya I, Tellis JC, Molander GA (2015) J Am Chem Soc 137:2195

    Article  CAS  Google Scholar 

  19. Molander GA, Gormisky PE (2008) J Org Chem 73:7481

    Article  CAS  Google Scholar 

  20. Molander GA, Beaumard F, Niethamer TK (2011) J Org Chem 76:8126

    Article  CAS  Google Scholar 

  21. Luo J, Zhang J (2016) ACS Catalys 6:873

    Article  CAS  Google Scholar 

  22. Yamashita Y, Tellis JC, Molander GA (2015) Proc Natl Acad Sci USA 112:12026

    Article  CAS  Google Scholar 

  23. Khatib ME, Serafim RAM, Molander GA (2016) Angew Chem Int Ed 55:254

    Article  Google Scholar 

  24. Muller K, Faeh C, Diederich F (2007) Science 317:1881

    Article  Google Scholar 

  25. Ryu D, Primer DN, Tellis JC, Molander GA (2016) Chem Eur J 22:120

    Article  CAS  Google Scholar 

  26. Ryu, DaWeon PhD (2015) Synthesis and applications of novel alkylboron compounds. Thesis, University of Pennsylvania, Philadelphia, PA, USA

  27. Karakaya I, Primer DN, Molander GA (2015) Org Lett 17:3294

    Article  CAS  Google Scholar 

  28. Amani J, Sodagar E, Molander GA (2016) Org Lett 18:732

    Article  CAS  Google Scholar 

  29. Matsuoka D, Nishigaichi Y (2015) Chem Lett 43:559

    Article  Google Scholar 

  30. Corcé V, Chamoreau L-M, Derat E, Goddard J-P, Ollivier C, Fensterbank L (2015) Angew Chem Int Ed 54:11414

    Article  Google Scholar 

  31. Levêque C, Chenneberg L, Corcé V, Goddard J-P, Ollivier C, Fensterbank L (2016) Org Chem Front 3:462

    Article  Google Scholar 

  32. Yasu Y, Koike T, Akita M (2012) Adv Synth Catal 354:3414

    Article  CAS  Google Scholar 

  33. Nishigaichi Y, Suzuki A, Takuwa A (2007) Tetrahedron Lett 48:211

    Article  CAS  Google Scholar 

  34. Jouffroy M, Primer DN, Molander GA (2016) J Am Chem Soc 138:47

    Article  Google Scholar 

  35. Patel NR, Kelly CB, Jouffroy M, Molander GA (2016) Org Lett 18:764

    Article  CAS  Google Scholar 

  36. Jouffroy M, Kelly CB, Molander GA (2016) Org Lett 18:876

    Article  CAS  Google Scholar 

  37. Zhou HB, Nettles KW, Bruning JB, Kim Y, Joachimiak A, Sharma S, Carlson KE, Stossi F, Katzenellenbogen BS, Greene GL, Katzenellenbogen JA (2007) Chem Biol 14:659

    Article  CAS  Google Scholar 

  38. Baldock C, Rafferty JB, Sedelnikova SE, Baker PJ, Stuitje AR, Slabas AR, Hawkes TR, Rice DW (1996) Science 274:2107

    Article  CAS  Google Scholar 

  39. Jouffroy M, Davies GHM, Molander GA (2016) Org Lett 18:1606

    Article  CAS  Google Scholar 

  40. Li H, Miao T, Wang M, Li P, Wang L (2016) Synlett. doi:10.1055/s-0035-1561388

    Google Scholar 

  41. Rodríguez N, Goossen L (2011) J Chem Soc Rev 40:5030

    Article  Google Scholar 

  42. Chou C-M, Chatterjee I, Studer A (2011) Angew Chem Int Ed 50:8614

    Article  CAS  Google Scholar 

  43. Shang R, Ji D-S, Chu L, Fu Y, Liu L (2001) Angew Chem Int Ed 50:4470

    Article  Google Scholar 

  44. Zao Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DWC (2014) Science 345:437

    Article  Google Scholar 

  45. Noble A, McCarver SJ, MacMillan DWC (2014) J Am Chem Soc 137:624

    Article  Google Scholar 

  46. Chu LC, Lipshultz JM, MacMillan DWC (2015) Angew Chem Int Ed 54:7929

    Article  CAS  Google Scholar 

  47. Zuo Z, Cong H, Li W, Choi J, Fu GC, MacMillan DWC (2016) J Am Chem Soc 138:1832

    Article  CAS  Google Scholar 

  48. Oderinde MS, Varela-Alvarez A, Aquila B, Robbins DW, Johannes JW (2015) J Org Chem 80:7642

    Article  CAS  Google Scholar 

  49. Sun ZY, Botros E, Su AD, Kim Y, Wang EJ, Baturay N, Kwon CH (2000) J Med Chem 43:4160

    Article  CAS  Google Scholar 

  50. Beletskaya IP, Ananikov VP (2011) Chem Rev 111:1596

    Article  CAS  Google Scholar 

  51. Hartwig JF (2008) Acc Chem Res 41:1534

    Article  CAS  Google Scholar 

  52. Dénes F, Pichowicz M, Povie G, Renaud P (2014) Chem Rev 114:2587

    Article  Google Scholar 

  53. Oderinde MS, Frenette M, Robbins DW, Aquila B, Johannes JW (2016) J Am Chem Soc 138:1760

    Article  CAS  Google Scholar 

  54. Larock RC, Yum EK (1991) J Am Chem Soc 113:6689

    Article  CAS  Google Scholar 

  55. Zhao D, Vásquez-Céspedes S, Glorius F (2015) Angew Chem In Ed 54:1657

    Article  CAS  Google Scholar 

  56. Tasker SZ, Jamison TF (2015) J Am Chem Soc 137:9531

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the National Institute of General Medical Sciences for a grant (R01 GM-113878) that has supported our research in this area. We are also grateful to Frontier Scientific and Evonik for supplying many of the materials used in our studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Gary A. Molander.

Additional information

This article is part of the Topical Collection “Ni- and Fe-Based Cross-Coupling Reactions”; edited by “Arkaitz Correa”.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cavalcanti, L.N., Molander, G.A. Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling. Top Curr Chem (Z) 374, 39 (2016). https://doi.org/10.1007/s41061-016-0037-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-016-0037-z

Keywords

Navigation