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Palladacycles incorporating a carboxylate-functionalized phosphine ligand: syntheses, characterization and their catalytic applications toward Suzuki couplings in water

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Abstract

A series of acetato-bridged [C^X]-type (C = aryl carbanion, X = N, P) palladacycles (1–5) of the general formula [Pd(μ-CH3COO)(C^X)]2 were synthesized as metal precursors via slightly modified procedures. However, in the case of complex 5 with Dpbp (Dpbp = 2′-(diphenylphosphino-κP)[1,1′-biphenyl]-2-yl-κC) as the supporting C^P ligand, an unexpected dinuclear complex [Pd(μ-CO2)(Dpbp)]2 (6) was obtained as a by-product and structurally determined by X-ray crystallography. The reactions of complexes 1–4 with 2-(diphenylphosphino)benzoic acid conveniently afforded four carboxylate-functionalized phosphine complexes [Pd(C^N)(Dpb)] (Dbp = 2-(diphenylphosphino-κP)benzoato-κO, 7–10), two of which (9/10) are newly synthesized in the present work and have been fully characterized. A comparative catalytic study revealed that complex [Pd(Ppy)(Dpb)] (7) (Ppy = 2-(2-pyridinyl-κN)phenyl-κC) is the best performer in Suzuki cross-couplings in H2O. In addition, complex 7 exhibits much better catalytic activity compared to the non-functionalized phosphine equivalent [Pd(OAc)(PPh3)(Ppy)] (11), which clearly indicates the superiority of incorporating a carboxylate-functionalized phosphine ligand into the palladacycles. A preliminary mechanistic study uncovered a different precatalyst initiation pathway compared to other known analogues of catalyst precursors.

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Notes

  1. For a book on palladacycles, see: [1].

  2. For a representative review, see: [2].

  3. For a representative review including the applications of palladacycles in material chemistry, see: [3].

  4. For representative reviews, see: [4,5,6,7,8,9,10,11,12,13,14].

  5. For very recent examples of complexes of the type I, see: [16,17,18,19,20,21].

  6. For representative reviews, see: [28,29,30].

  7. For reviews on Suzuki couplings in H2O, see: [36]. For some very recent examples, see: [37,38,39,40,41,42].

  8. The term transphobia effect was first coined by Vicente and Jones’s groups. For this paper, see: [56].

  9. For selected reviews on Suzuki couplings catalyzed by palladium complexes, see: [30, 60,61,62,63,64]. For selected examples on Suzuki couplings using palladium N-heterocyclic carbene complexes: see: [65].

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Acknowledgements

The authors thank Beijing Natural Science Foundation (Grant No. 2164057) and National Natural Science Foundation of China (Grant No. 21502122) for financial support. In particular, we thank Dr. Wei Wei and Dr. Deng Xuebin for refining the X-ray molecular structures.

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  1. Department of Chemistry, Capital Normal University, Beijing, People’s Republic of China

    Xin Zhang, Haiying Wang, Jiali Yuan & Shuai Guo

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Correspondence to Shuai Guo.

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Zhang, X., Wang, H., Yuan, J. et al. Palladacycles incorporating a carboxylate-functionalized phosphine ligand: syntheses, characterization and their catalytic applications toward Suzuki couplings in water. Transit Met Chem 42, 727–738 (2017). https://doi.org/10.1007/s11243-017-0181-5

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