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Solvias Launches New Josiphos Nickel Catalysts

Solvias now offers a series of air-stable Josiphos nickel catalysts. These catalysts promote the challenging amination of aryl halides and sulfonates with ammonia as well as ammonium salts.

The cost and relative scarcity of palladium provides motivation for the development of alternative, more earth-abundant catalysts. Following this trend, the latest publications indicate a rapid expansion of the employment of nickel in homogeneous catalysis, especially in the field of C-X and C-C cross coupling reactions.[1] It has come to our attention that ligands of the Josiphos family - developed by Solvias - play a key role in these developments.[2] However, no commercial source for readily applicable and air-stable Josiphos nickel catalysts has been available until now.

Scheme 1: New Josiphos Nickel Catalysts

In order to advance the application of nickel catalysts in academic research as well as in industrial process development, Solvias has commercialized a series of air-stable Josiphos nickel catalysts. These [Ni(Josiphos)(4-PhCN)Cl]-type catalysts readily undergo reductive elimination under formation of catalytically active Ni(0) complexes. In the preparation of these catalysts Solvias made use of recent findings that describe benzonitrile to act as a ligand for the crucial Ni(0) species improving activity or stability of this intermediate.[3]

Scheme 2: Nickel-catalyzed Amination of Aryl Halides

The successful application of Josiphos nickel catalysts has been described in a number of prominent publications on C(sp2)–N cross-coupling, especially under the employment of ammonia. Selected examples of such reports include

  1. Nickel-Catalyzed Amination of Aryl Chlorides with Ammonia or Ammonium Salts[4]
  2. Nickel-Catalyzed Monoarylation of Ammonia[5]
  3. A Comparative Reactivity Survey of Some Prominent Bisphosphine Nickel(II) Precatalysts in C−N Cross-Coupling[6]
  4. Nickel-Catalyzed Amination Reactions: An Overview[7]

Our established supply chain enables us to provide these new products from our high-quality catalyst portfolio in industrially relevant amounts. Research quantities of our new Josiphos Nickel Catalysts are available from Sigma Aldrich and STREM.

Want to know more? Don’t hesitate to contact us!

[1] S. Z. Tasker, E. A. Standley, T. F. Jamison, Nature 2014, 509, 299.
[2] J. Schranck, J. Rotzler, Org. Proc. Res. Dev. 2015, 19, 1936.
[3] S. Ge, R. A. Green, J. F. Hartwig, J. Am. Chem. Soc. 2014, 136, 1617.
[4] R. A. Green, J. F. Hartwig, Angew. Chem. Int. Ed. 2015, 54, 3768.
[5] A. Borzenko, N. L. Rotta-Loria, P. M. MacQueen, C. M. Lavoie, R. McDonald, M. Stradiotto, Angew. Chem. Int. Ed. 2015, 54, 3773.
[6] J.S. K. Clark, C. M. Lavoie, P. M. MacQueen, M. J. Ferguson, M. Stradiotto, Organometallics 2016, 35, 3248.
[7] M. Marin, R. J. Rama, M. C. Nicasio, Chem. Rec. 2016, 16, 1819.

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