Air-Stable Ni(0) Complex Ni(COD)(DQ), a Useful Precatalyst

(1,5-Cyclooctadiene)(duroquinone)nickel(0) (Ni(COD)(DQ), 1) was reported to be an air-stable precatalyst for a variety of nickel-catalyzed reactions by Engle et al.¹⁾ For example, 1 gave comparable results to the Ni(0) complex bis(1,5-cyclooctadiene)nickel (Ni(COD)₂), which is sensitive to air and heat, and other nickel(II) complexes in various reactions, including Suzuki-Miyaura cross-coupling and Buchwald-Hartwig amination. In addition, the synthesis of N,N-diarylsulfonamides through C-N cross-coupling using 1 as a catalyst²⁾ and the deoxygenative alkenylation of carboxylic acids to give all-carbon tetrasubstituted alkenes using 1 and a photoredox catalyst³⁾ have been reported. Therefore, further development and application of reactions using 1 are anticipated in the future.

References

• 1) Ni(COD)(DQ): An Air-Stable 18-Electron Nickel(0)–Olefin Precatalyst
• • V. T. Tran, Z.-Q. Li, O. Apolinar, J. Derosa, M. V. Joannou, S. R. Wisniewski, M. D. Eastgate, K. M. Engle, Angew. Chem. Int. Ed. 2020, 59, 7409.
• 2) Ni(cod)(duroquinone)-Catalyzed C–N Cross-Coupling for the Synthesis of N,N-Diarylsulfonamides
• • T. You, J. Li, Org. Lett. 2022, 24, 6642.
• 3) Highly selective synthesis of all-carbon tetrasubstituted alkenes by deoxygenative alkenylation of carboxylic acids
• • Y. Li, Q. Shao, H. He, C. Zhu, X.-S. Xue, J. Xie, Nat. Commun. 2022, 13, 10.

Related Compounds

B6553

Bis(1,5-cyclooctadiene)nickel(0) (= Ni(COD)₂)

B2027

1,1'-Bis(diphenylphosphino)ferrocene (= dppf)

S0450

Sodium tert-Butoxide

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