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Tunable cobalt-catalysed hydrogenation of allenes enabled by multiple metal–ligand cooperative functionalities

Nature Chemistry volume 17, pages 1469–1479 (2025)Cite this article

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Abstract

Catalytic hydrogenation is essential in synthetic chemistry, with ongoing innovations aimed at enhancing the selectivity and efficiency of these reactions. The hydrogenation of multisubstituted allenes, however, presents a long-standing challenge due to the difficulty of controlling multiple selectivity factors simultaneously. Here we introduce a series of chiral pincer cobalt catalysts featuring multiple metal–ligand cooperative functionalities. These catalysts feature an ‘N–H’ moiety as an outer-sphere binding site and an N-heterocycle group as a hemilabile basic site, enabling the use of structurally diverse tridentate ligands for selective hydrogenation of functionalized allenes. This design liberates a coordination site for H2 activation and enhances selectivity control through the structural tuning of the N-heterocycle group. The catalysts exhibit exceptional chemo-, regio-, enantio- and Z/E-selectivities, along with broad functional group tolerance, enabling access to all possible semihydrogenation products of multisubstituted allenes. Mechanistic studies uncover a distinctive redox-neutral Co(I) catalytic cycle that facilitates heterolytic cleavage of H2, assisted by the basic N-heterocycle on the ligand.

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Fig. 1: Divergent and selective hydrogenation of multisubstituted allenes.
Fig. 2: Overview of reaction development.
Fig. 3: Mechanistic investigations.
Fig. 4: Computational investigations.

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Data availability

The data that support the findings of this study are available in this Article and its Supplementary Information. The crystallographic data for the structures reported in this Article have been deposited at the Cambridge Crystallographic Data Centre under deposition numbers CCDC 2345206 (11), 2345208 (RL7-CoCl2), 2397603 (RL11-CoCl2), 2345207 (RL12-CoCl2), 2397604 (RL14-CoCl2), 2397605 (RL15-CoCl2) and 2397606 (RL17-CoCl2). Copies of the data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures.

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Acknowledgements

We thank H. Jiao from Leibniz Institute for Catalysis and S. Liu from Henan University for helpful discussions. Financial support from the National Natural Science Foundation of China (grant nos. 22225103 (Q.L.) and 22202123 (Z.W.)) and the Tsinghua University Initiative Scientific Research Program are greatly appreciated.

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Author notes

  1. These authors contributed equally: Xianle Rong, Yunjuan Ren.

Authors and Affiliations

  1. China Engineering Research Center of Advanced Rare Earth Materials (Ministry of Education), Center of Basic Molecular Science, Department of Chemistry, Tsinghua University, Beijing, China

    Xianle Rong, Yongshun Chen, Chongyao Li & Qiang Liu

  2. Institute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of Ministry of Education, Key Laboratory of Energy Storage Materials Innovation and Integration of Shanxi Province, Shanxi University, Taiyuan, China

    Yunjuan Ren & Zhihong Wei

  3. Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, Shanghai, China

    Jie Wang, Zhaoqiang Chen & Shengming Ma

  4. Department of Chemistry, Southern University of Science and Technology, Shenzhen, China

    Lizhi Tao

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  1. Xianle Rong
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Contributions

Conceptualization: X.R., S.M. and Q.L. Methodology: X.R. and Y.R. Investigation: X.R., Y.R., Y.C., C.L., J.W., Z.C. and L.T. Funding acquisition: Z.W. and Q. L. Project administration: L.T., S.M., Z.W. and Q.L. Supervision: L.T., S.M., Z.W. and Q.L. Writing—original draft: X.R., Z.W. and Q.L. Writing—review and editing: X.R. and Q.L.

Corresponding authors

Correspondence to Lizhi Tao, Zhihong Wei, Shengming Ma or Qiang Liu.

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Extended data

Extended Data Fig. 1 Structure of cobalt catalysts.

a, Solid-state structure of RL7-CoCl2 and RL12-CoCl2 determined by single-crystal X-ray diffraction. Ellipsoids set at 50% probability. Hydrogen atoms are omitted for clarity. Colour code for the atoms in the structures: grey, carbon; light blue, nitrogen; red, oxygen; purple, phosphorus; green, chlorine; royal blue, iron; dark blue, cobalt. b, Dissociation free energy of the N-heterocyclic ligand. T and B denote tridentate and bidentate coordination structures, respectively, and superscript Q indicates quartet spin states. ΔG values (in kcal mol−1) were calculated at the M06L/def2-TZVP/SMD(DMAc)//M06L/def2-SVP level.

Extended Data Fig. 2 Tunable cobalt-catalyzed hydrogenation of racemic trisubstituted allenes.

a, Divergent hydrogenation of racemic trisubstituted allenes. b, Substrate scope of asymmetric 1,2-hydrogenation of racemic allenes. Reaction conditions: a rac-5 (0.25 mmol), Co(BF4)2.6H2O (2 mol%), RL7 or SL7 (2.2 mol%) and zinc dust (20 mol%) in 1 mL of DMAc at 40 °C for 20 h. Isolated yields (%) were given, regioselective ratio (r.r. 6/7) was determined by 31P NMR and enantiomeric excess (% e.e.) was determined by chiral-phase HPLC. b CoCl2 (2 mol%), RL12 (2.2 mol%) and zinc dust (20 mol%) in HFIP (1 mL) at 60 °C for 20 h. E/Z ratio was determined by 31P NMR. c CoCl2 (2 mol%), RL16 (2.2 mol%) and zinc dust (20 mol%) in DMAc (1 mL) at 60 °C for 40 h. Z/E ratio was determined by 31P NMR.

Extended Data Fig. 3 Catalytic cycle.

Proposed mechanism for the stereoselective cobalt-catalyzed hydrogenation of functionalized allenes. DFT calculations were performed at the M06L/Def2-TZVP/SMD(DMAc)//M06L/Def2-SVP level of theory.

Extended Data Fig. 4 Synthetic Applications.

a, Syntheses of deuterated trisubstituted alkene products. b, Gram-scale synthesis with 0.2 mol% catalyst. c, Post functionalisation of reaction products. d, Preparation of intermediate of phosphonomethyl-phenylalanine analogue. i Lawesson’s reagent, toluene, 100 °C. ii TMSBr, DCM, r.t. iii mCPBA, −20 °C. iv NBS, DMSO/H2O (v/v = 7/5), r.t. v NIS, DMSO/H2O (v/v = 7/5), r.t. vi 1) BH3, THF, -20 °C, 2) H2O2, NaOAc, 0 °C. vii 1) Pd(PPh3)4 (2 mol%), CuI (2 mol%), 3-Methyl butynol and Et3N, 80 °C. 2) P(OEt)2Cl, Et3N, DCM, −78 °C - r.t. viii Co(BF4)2·6H2O (2 mol%), RL7 (2.2 mol%) and zinc dust (5 mol%) in 1 mL of DMAc under H2 (30 bar) at 40 °C for 20 h.

Supplementary information

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Supplementary Figs. 1–49, Supplementary Tables 1–13, Experimental procedures and characterization data, DFT calculation results, Discussion and References.

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x,y,z coordinates for DFT calculations.

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Rong, X., Ren, Y., Chen, Y. et al. Tunable cobalt-catalysed hydrogenation of allenes enabled by multiple metal–ligand cooperative functionalities. Nat. Chem. 17, 1469–1479 (2025). https://doi.org/10.1038/s41557-025-01945-2

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