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Open AccessOpen Access JUSTC Chemistry 05 July 2023

Mechanism of nickel-catalyzed hydroalkylation of branched 1,3-dienes

  • 1.

    Hefei National Research Center for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, University of Science and Technology of China, Hefei 230026, China

  • 2.

    Department of Chemistry, Center for Atomic Engineering of Advanced Materials, Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Anhui University, Hefei 230601, China

Cite this:
https://doi.org/10.52396/JUSTC-2023-0031
More Information
  • Author Bio:

    Mingqiang Liu is a master’s student under the supervision of Prof. Yao Fu at the University of Science and Technology of China. His research mainly focuses on DFT calculations of the reaction mechanism

    Haizhu Yu received her Ph.D. degree from the University of Science and Technology of China. She is currently a Professor at Anhui University. Her research focuses on reaction mechanism simulation, structure-activity relationships, and anticancer metal nanoclusters

    Yao Fu received his Ph.D. degree from the University of Science and Technology of China in 2005. He is currently a Professor at the University of Science and Technology of China. His research focuses on physical organic chemistry, green organic synthesis, and the biomass chemical industry

  • Corresponding author: E-mail: yuhaizhu@ahu.edu.cn; E-mail: fuyao@ustc.edu.cn
  • Received Date: 05 March 2023
  • Accepted Date: 23 May 2023
    • Available Online: 05 July 2023
    Abstract

  • Abstract

    With the development of algorithms and theoretical chemistry, quantum chemical calculations have been used to explain and predict various chemical experiments. The hydroalkylation of conjugated olefins catalyzed by nickel is an important type of organic chemical reaction, and its mechanism has always been the focus of organic chemists. In this paper, a hydroalkylation reaction developed by the Mazet research group was studied in detail by means of density functional theory (DFT), and a possible mechanism model of the reaction was obtained. In this context, the attractive regioselectivity of the reaction was explored and rationally explained.

    Graphical abstract

    Origin of regioselectivity in nickel-catalyzed hydroalkylation of branched 1, 3-dienes.

    Abstract

    With the development of algorithms and theoretical chemistry, quantum chemical calculations have been used to explain and predict various chemical experiments. The hydroalkylation of conjugated olefins catalyzed by nickel is an important type of organic chemical reaction, and its mechanism has always been the focus of organic chemists. In this paper, a hydroalkylation reaction developed by the Mazet research group was studied in detail by means of density functional theory (DFT), and a possible mechanism model of the reaction was obtained. In this context, the attractive regioselectivity of the reaction was explored and rationally explained.

    • Public Summary

    • The mechanism of Ni-catalyzed hydroalkylation of branched 1,3-dienes was systematically explored with the aid of DFT.
    • Reaction mechanism consists of four main steps: proton transfer, anion dissociation, carbanion attack and ligand exchange.
    • The selectivity of the reaction was analyzed, which is mainly due to the electronic and steric effects.

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    • References(73)
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    Figure  1.  Examples of the typical hydroalkylation strategies of diene.

    Figure  2.  Possible reaction mechanism of the Ni-catalyzed hydroalkylation of 2-phenyl-1,3-diene.

    Figure  3.  Model reaction in the theoretical calculations.

    Figure  4.  The Gibbs free energy profiles of the hydrogenation step start from IN1.

    Figure  5.  The Gibbs free energy profiles for the C–C bond formation steps from IN3.

    Figure  6.  The Gibbs free energy profile of the most feasible hydroalkylation of the 2-phenyl-1,3-diene with the amide reagent.

    Figure  7.  Energy profile of the main transformations in the most feasible hydroalkylation pathway of the imide system.

    Figure  8.  The Lewis structure, relative Gibbs free energy (ΔG° in kcal/mol), and optimized geometry of IN2 and IN2-a.

    Figure  9.  (a, b) Illustrative diagram for the configuration of the C1- and C3-alkylation transition states. The nickel on the other side is omitted for ease of observation. (c) The relative Gibbs free energy (ΔG° in kcal/mol), the NBO charge of the carbonyl group and the optimized geometry of Ⅰ, Ⅱ, Ⅲ, Ⅳ and Ⅴ.

    [1]
    Volla C M R, Atodiresei I, Rueping M. Catalytic C–C bond-forming multi-component cascade or domino reactions: Pushing the boundaries of complexity in asymmetric organocatalysis. Chem. Rev., 2014, 114: 2390–2431. doi: 10.1021/cr400215u
    [2]
    Jacobsen E N, Pfaltz A, Yamamoto H. Comprehensive Asymmetric Catalysis. Berlin: Springer-Verlag, 1999.
    [3]
    Adamson N J, Malcolmson S J. Catalytic enantio- and regioselective addition of nucleophiles in the intermolecular hydrofunctionalization of 1,3-dienes. ACS Catal., 2020, 10: 1060–1076. doi: 10.1021/acscatal.9b04712
    [4]
    Hartwig J F. Carbon-heteroatom bond formation catalysed by organometallic complexes. Nature, 2008, 455: 314–322. doi: 10.1038/nature07369
    [5]
    Zeng X M. Recent advances in catalytic sequential reactions involving hydroelement addition to carbon-carbon multiple bonds. Chem. Rev., 2013, 113: 6864–6900. doi: 10.1021/cr400082n
    [6]
    Dong Z, Ren Z, Thompson S J, et al. Transition-metal-catalyzed C–H alkylation using alkenes. Chem. Rev., 2017, 117: 9333–9403. doi: 10.1021/acs.chemrev.6b00574
    [7]
    Leitner A, Larsen J, Steffens C, et al. Palladium-catalyzed addition of mono- and dicarbonyl compounds to conjugated dienes. J. Org. Chem., 2004, 69: 7552–7557. doi: 10.1021/jo0490999
    [8]
    Yang H J, Xing D. Palladium-catalyzed diastereo- and enantioselective allylic alkylation of oxazolones with 1,3-dienes under base-free conditions. Chem. Commun., 2020, 56: 3721–3724. doi: 10.1039/D0CC00265H
    [9]
    Liao L Y, Sigman M S. Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of π-allyl palladium intermediates under oxidative conditions. J. Am. Chem. Soc., 2010, 132 (30): 10209–10211. doi: 10.1021/ja105010t
    [10]
    Zhang Z P, Xiao F, Wu H M, et al. Pd-catalyzed asymmetric hydroalkylation of 1,3-dienes: Access to unnatural α-amino acid derivatives containing vicinal quaternary and tertiary stereogenic centers. Org. Lett., 2020, 22 (2): 569–574. doi: 10.1021/acs.orglett.9b04341
    [11]
    Tran G, Mazet C. Ni-catalyzed regioselective hydroalkoxylation of branched 1,3-dienes. Org. Lett., 2019, 21 (22): 9124–9127. doi: 10.1021/acs.orglett.9b03511
    [12]
    Shirakawa E, Takahashi G, Tsuchimoto T, et al. Nickel-catalysed addition of organoboronates to 1,3-dienes. Chem. Commun., 2002: 2210–2211. doi: 10.1039/B207185A
    [13]
    Lv L Y, Yu L, Qiu Z H, et al. Switch in selectivity for formal hydroalkylation of 1,3-dienes and enynes with simple hydrazones. Angew. Chem. Int. Ed., 2020, 59: 6466–6472. doi: 10.1002/anie.201915875
    [14]
    Wang S, Xiang Y F, Chen T T, et al. Construction of quaternary carbon centers by KOtBu-catalyzed α-homoallylic alkylation of lactams with 1,3-dienes. Org. Chem. Front., 2022, 9: 1642–1648. doi: 10.1039/d1qo01927a
    [15]
    Flaget A, Zhang C, Mazet C. Ni-catalyzed enantioselective hydrofunctionalizations of 1,3-dienes. ACS. Catal., 2022, 12 (24): 15638–15647. doi: 10.1021/acscatal.2c05251
    [16]
    Goldfogel M J, Meek S J. Diastereoselective synthesis of vicinal tertiary and N-substituted quaternary stereogenic centers by catalytic hydroalkylation of dienes. Chem. Sci., 2016, 7: 4079–4084. doi: 10.1039/C5SC04908C
    [17]
    Pang X B, Zhao Z Z, Wei X X, et al. Regiocontrolled reductive vinylation of aliphatic 1,3-dienes with vinyl triflates by nickel catalysis. J. Am. Chem. Soc., 2021, 143 (12): 4536–4542. doi: 10.1021/jacs.1c00142
    [18]
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