Carboximidamide Ligands for Reductive Cross-Electrophile Coupling

Reductive cross-electrophile couplings (CEC) are C(sp²)-C(sp³) cross-coupling reactions between aryl halides and alkyl halides,¹⁾ redox-active alkyl carboxylic acids,²⁾ and so on. In these reactions, nickel complexes with the following carboximidamides (PyBCam·HCl, PyBCam^CN, PyCam·HCl, PyCam^CN, ^tBuBpyCam^CN) as ligands are used as catalysts. CEC does not require organometallic reagents utilized in conventional coupling reactions, such as organozinc compounds, and organoboron compounds. Therefore, coupling partners are readily available and easy to handle. These ligands are expected to be useful for connecting various alkyl groups into core aromatic rings in drug discovery research.³⁾

Related Products

P3015

Pyridine-2,6-dicarboximidamide Dihydrochloride (= PyBCam·HCl)

D6070

N²,N⁶-Dicyanopyridine-2,6-bis(carboximidamide) (= PyBCam^CN)

P2176

Picolinimidamide Hydrochloride (= PyCam·HCl)

C3801

N'-Cyano-2-pyridinecarboximidamide (= PyCam^CN)

C3803

4,4'-Di-tert-Butyl-N-cyano[2,2'-bipyridine]-6-carboximidamide (= ^tBuBpyCam^CN)

N1051

Nickel(II) Chloride Ethylene Glycol Dimethyl Ether Complex (= NiCl₂(DME))

N1298

Nickel(II) Bromide Ethylene Glycol Dimethyl Ether Complex (= NiBr₂(DME))

Z0015

Zinc (Powder)

H0395

N-Hydroxyphthalimide (= NHPI)

S0564

Sodium Iodide (= NaI)

T0431

Trifluoroacetic Acid (= TFA)

D0254

N,N'-Diisopropylcarbodiimide (= DIC)

D1450

4-Dimethylaminopyridine (= DMAP)

References

• 1) Coupling of Challenging Heteroaryl Halides with Alkyl Halides via Nickel-Catalyzed Cross-Electrophile Coupling
  • E. C. Hansen, C. Li, S. Yang, D. Pedro, D. J. Weix, J. Org. Chem. 2017, 82, 7085.
• 2) Control of Redox-Active Ester Reactivity Enables a General Cross-Electrophile Approach to Access Arylated Strained Rings
  • D. C. Salgueiro, B. K. Chi, I. A. Guzei, P. G. Reynaga, D. J. Weix, Angew. Chem. Int. Ed. 2022, 61, e202205673.
• 3) Expanding the Medicinal Chemist Toolbox: Comparing Seven C(sp²)−C(sp³) Cross-Coupling Methods by Library Synthesis
  • A. W. Dombrowski, N. J. Gesmundo, A. L. Aguirre, K. A. Sarris, J. M. Young, A. R. Bogdan, M. C. Martin, S. Gedeon, Y. Wang, ACS Med. Chem. Lett. 2020, 11, 597.

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