Skip to main content

Thank you for visiting nature.com. You are using a browser version with limited support for CSS. To obtain the best experience, we recommend you use a more up to date browser (or turn off compatibility mode in Internet Explorer). In the meantime, to ensure continued support, we are displaying the site without styles and JavaScript.

  • Review Article
  • Published:

Recent advances in homogeneous nickel catalysis

An Erratum to this article was published on 14 May 2014

Abstract

Tremendous advances have been made in nickel catalysis over the past decade. Several key properties of nickel, such as facile oxidative addition and ready access to multiple oxidation states, have allowed the development of a broad range of innovative reactions. In recent years, these properties have been increasingly understood and used to perform transformations long considered exceptionally challenging. Here we discuss some of the most recent and significant developments in homogeneous nickel catalysis, with an emphasis on both synthetic outcome and mechanism.

This is a preview of subscription content, access via your institution

Access options

Rent or buy this article

Prices vary by article type

from$1.95

to$39.95

Prices may be subject to local taxes which are calculated during checkout

Figure 1: Nickel fundamentals.
Figure 2: Recent nickel-catalysed Suzuki–Miyaura arylations.
Figure 3: Halogen alternatives used in cross-coupling reactions.
Figure 4: Milestones in cross-coupling reactions of aryl ethers and esters.
Figure 5: Reactions of benzylic alcohols and alcohol derivatives.
Figure 6: Nickel-catalysed Negishi-type cross-coupling of aromatic and aliphatic aziridines.
Figure 7: Key representative examples of cross-coupling reactions involving oxidative addition to sp3 carbon electrophiles.
Figure 8: Proposed mechanisms for C(sp3)–C(sp3) cross-coupling.
Figure 9: Asymmetric C(sp3)–C(sp3) cross-coupling reactions.
Figure 10: Reductive cross-coupling reactions.
Figure 11: Selected examples of nickel-catalysed C–H activation reactions.
Figure 12: Nickel-catalysed Heck reactions.
Figure 13: Prototypical reductive coupling reactions and use of new reducing agents.
Figure 14: Two strategies for regiocontrol in reductive coupling reactions.

Similar content being viewed by others

References

  1. Wilke, G. Contributions to organo-nickel chemistry. Angew. Chem. Int. Edn Engl. 27, 185–206 (1988)

    Article  Google Scholar 

  2. Tamaru Y., ed. Modern Organonickel Chemistry (Wiley-VCH, 2005)An excellent discussion of nickel catalysis in general.

  3. Montgomery, J. Nickel-catalyzed reductive cyclizations and couplings. Angew. Chem. Int. Edn 43, 3890–3908 (2004)A comprehensive review of reductive coupling before 2004.

    Article  CAS  Google Scholar 

  4. Diederich F., Stang P. J., eds. Metal-Catalyzed Cross-Coupling Reactions (Wiley-VCH, 1998)

  5. Tsou, T. T. & Kochi, J. K. Mechanism of oxidative addition. Reaction of nickel(0) complexes with aromatic halides. J. Am. Chem. Soc. 101, 6319–6332 (1979)An excellent investigation into the mechanism of oxidative addition of Ni(0) into aryl halides and the factors determining rate, selectivity and solvent effects of such reactions.

    Article  CAS  Google Scholar 

  6. Lanni, E. L. & McNeil, A. J. Mechanistic studies on Ni(dppe)Cl2-catalyzed polymerizations: evidence for rate-determining reductive elimination. J. Am. Chem. Soc. 131, 16573–16579 (2009)

    Article  CAS  PubMed  Google Scholar 

  7. Li, B.-J., Yu, D.-G., Sun, C.-L. & Shi, Z.-J. Activation of “inert” alkenyl/aryl C–O bond and its application in cross-coupling reactions. Chemistry 17, 1728–1759 (2011)A detailed account of cross-coupling reactions of phenol derivatives of all types, including those catalysed by metals other than nickel.

    Article  CAS  PubMed  Google Scholar 

  8. Rosen, B. M. et al. Nickel-catalyzed cross-couplings involving carbon–oxygen bonds. Chem. Rev. 111, 1346–1416 (2011)

    Article  CAS  PubMed  Google Scholar 

  9. Mesganaw, T. & Garg, N. K. Ni- and Fe-catalyzed cross-coupling reactions of phenol derivatives. Org. Process Res. Dev. 17, 29–39 (2013)

    Article  CAS  Google Scholar 

  10. Garcia, J. J., Brunkan, N. M. & Jones, W. D. Cleavage of carbon–carbon bonds in aromatic nitriles using nickel(0). J. Am. Chem. Soc. 124, 9547–9555 (2002)

    Article  CAS  PubMed  Google Scholar 

  11. Tobisu, M., Xu, T., Shimasaki, T. & Chatani, N. Nickel-catalyzed Suzuki–Miyaura reaction of aryl fluorides. J. Am. Chem. Soc. 133, 19505–19511 (2011)

    Article  CAS  PubMed  Google Scholar 

  12. Cornella, J., Gómez-Bengoa, E. & Martin, R. Combined experimental and theoretical study on the reductive cleavage of inert C–O bonds with silanes: ruling out a classical Ni(0)/Ni(II) catalytic couple and evidence for Ni(I) intermediates. J. Am. Chem. Soc. 135, 1997–2009 (2013)A rigorous experimental and computational study of the hypothesized nickel( i )-based catalytic cycle.

    Article  CAS  PubMed  Google Scholar 

  13. O’Connor, C. T. & Kojima, M. Alkene oligomerization. Catal. Today 6, 329–349 (1990)

    Article  Google Scholar 

  14. Massera, C. & Frenking, G. Energy partitioning analysis of the bonding in L2TM–C2H2 and L2TM–C2H4 (TM = Ni, Pd, Pt; L2 = (PH3)2, (PMe3)2, H2PCH2PH2, H2P(CH2)2PH2). Organometallics 22, 2758–2765 (2003)

    Article  CAS  Google Scholar 

  15. Lin, B.-L. et al. Comparing nickel- and palladium-catalyzed Heck reactions. Organometallics 23, 2114–2123 (2004)

    Article  CAS  Google Scholar 

  16. Cordero, B. et al. Covalent radii revisited. Dalton Trans. 2832–2838 (2008)

  17. Yamaguchi, J., Muto, K. & Itami, K. Recent progress in nickel-catalyzed biaryl coupling. Eur. J. Org. Chem. 19–30 (2013)A concise overview of the state of biaryl synthesis by a variety of nickel-catalysed methods.

  18. Ge, S. & Hartwig, J. F. Highly reactive, single-component nickel catalyst precursor for Suzuki–Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides. Angew. Chem. Int. Edn 51, 12837–12841 (2012)

    Article  CAS  Google Scholar 

  19. Ramgren, S. D., Hie, L., Ye, Y. & Garg, N. K. Nickel-catalyzed Suzuki–Miyaura couplings in green solvents. Org. Lett. 15, 3950–3953 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. Chuit, C., Felkin, H., Frajerman, C., Roussi, G. & Swierczewski, G. Action des organomagnesiens sur les alcools allyliques en presence de complexes du nickel: I. Synthese d’olefines. J. Organomet. Chem. 127, 371–384 (1977)

    Article  CAS  Google Scholar 

  21. Kocienski, P. & Dixon, N. J. Stereoselective synthesis of homoallylic alcohols by migratory insertion reactions of higher-order cyanocuprates and nickel-catalysed coupling reactions involving enol carbamates. Synlett 1989, 52–54 (1989)

    Google Scholar 

  22. Sengupta, S., Leite, M., Raslan, D. S., Quesnelle, C. & Snieckus, V. Nickel(0)-catalyzed cross coupling of aryl O-carbamates and aryl triflates with Grignard reagents. Directed ortho metalation-aligned synthetic methods for polysubstituted aromatics via a 1,2-dipole equivalent. J. Org. Chem. 57, 4066–4068 (1992)

    Article  CAS  Google Scholar 

  23. Milburn, R. R. & Snieckus, V. The tertiary sulfonamide as a latent directed-metalation group: Ni0-catalyzed reductive cleavage and cross-coupling reactions of aryl sulfonamides with Grignard reagents. Angew. Chem. Int. Edn 43, 888–891 (2004)

    Article  CAS  Google Scholar 

  24. Dankwardt, J. W. Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: an efficient synthesis of unsymmetrical biaryls. Angew. Chem. Int. Edn 43, 2428–2432 (2004)

    Article  CAS  Google Scholar 

  25. Tobisu, M., Shimasaki, T. & Chatani, N. Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters. Angew. Chem. Int. Edn 47, 4866–4869 (2008)

    Article  CAS  Google Scholar 

  26. Guan, B.-T., Wang, Y., Li, B.-J., Yu, D.-G. & Shi, Z.-J. Biaryl construction via Ni-catalyzed C–O activation of phenolic carboxylates. J. Am. Chem. Soc. 130, 14468–14470 (2008)

    Article  CAS  PubMed  Google Scholar 

  27. Quasdorf, K. W., Tian, X. & Garg, N. K. Cross-coupling reactions of aryl pivalates with boronic acids. J. Am. Chem. Soc. 130, 14422–14423 (2008)

    Article  CAS  PubMed  Google Scholar 

  28. Li, B.-J. et al. Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C–O bond activation under mild reaction conditions. Angew. Chem. Int. Edn 47, 10124–10127 (2008)

    Article  Google Scholar 

  29. Yu, D.-G. et al. Direct application of phenolic salts to nickel-catalyzed cross-coupling reactions with aryl Grignard reagents. Angew. Chem. Int. Edn 49, 4566–4570 (2010)

    Article  CAS  Google Scholar 

  30. Yu, D.-G. & Shi, Z.-J. Mutual activation: Suzuki–Miyaura coupling through direct cleavage of the sp2 C–O bond of naphtholate. Angew. Chem. Int. Edn 50, 7097–7100 (2011)

    Article  CAS  Google Scholar 

  31. Quasdorf, K. W. et al. Suzuki–Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies. J. Am. Chem. Soc. 133, 6352–6363 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Antoft-Finch, A., Blackburn, T. & Snieckus, V. N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki–Miyaura cross-coupling partner. J. Am. Chem. Soc. 131, 17750–17752 (2009)

    Article  CAS  PubMed  Google Scholar 

  33. Ehle, A. R., Zhou, Q. & Watson, M. P. Nickel(0)-catalyzed Heck cross-coupling via activation of aryl C–OPiv bonds. Org. Lett. 14, 1202–1205 (2012)

    Article  CAS  PubMed  Google Scholar 

  34. Tobisu, M., Yasutome, A., Yamakawa, K., Shimasaki, T. & Chatani, N. Ni(0)/NHC-catalyzed amination of N-heteroaryl methyl ethers through the cleavage of carbon–oxygen bonds. Tetrahedron 68, 5157–5161 (2012)

    Article  CAS  Google Scholar 

  35. Hie, L., Ramgren, S. D., Mesganaw, T. & Garg, N. K. Nickel-catalyzed amination of aryl sulfamates and carbamates using an air-stable precatalyst. Org. Lett. 14, 4182–4185 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Álvarez-Bercedo, P. & Martin, R. Ni-catalyzed reduction of inert C−O bonds: a new strategy for using aryl ethers as easily removable directing groups. J. Am. Chem. Soc. 132, 17352–17353 (2010)

    Article  CAS  PubMed  Google Scholar 

  37. Guan, B.-T. et al. Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C–O activation. J. Am. Chem. Soc. 130, 3268–3269 (2008)

    Article  CAS  PubMed  Google Scholar 

  38. Taylor, B. L. H., Swift, E. C., Waetzig, J. D. & Jarvo, E. R. Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: enantioselective synthesis of diarylethanes. J. Am. Chem. Soc. 133, 389–391 (2011)

    Article  CAS  PubMed  Google Scholar 

  39. Greene, M. A., Yonova, I. M., Williams, F. J. & Jarvo, E. R. Traceless directing group for stereospecific nickel-catalyzed alkyl−alkyl cross-coupling reactions. Org. Lett. 14, 4293–4296 (2012)

    Article  CAS  PubMed  Google Scholar 

  40. Harris, M. R., Hanna, L. E., Green, M. A., Moore, C. E. & Jarvo, E. R. Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst. J. Am. Chem. Soc. 135, 3303–3306 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Zhou, Q., Srinivas, H. D., Dasgupta, S. & Watson, M. P. Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes. J. Am. Chem. Soc. 135, 3307–3310 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Yu, D.-G. et al. Direct arylation/alkylation/magnesiation of benzyl alcohols in the presence of Grignard reagents via Ni-, Fe-, or Co-catalyzed sp3 C–O bond activation. J. Am. Chem. Soc. 134, 14638–14641 (2012)

    Article  CAS  PubMed  Google Scholar 

  43. León, T., Correa, A. & Martin, R. Ni-catalyzed direct carboxylation of benzyl halides with CO2 . J. Am. Chem. Soc. 135, 1221–1224 (2013)

    Article  CAS  PubMed  Google Scholar 

  44. Correa, A., León, T. & Martin, R. Ni-catalyzed carboxylation of C(sp2)– and C(sp3)–O bonds with CO2 . J. Am. Chem. Soc. 136, 1062–1069 (2014)

    Article  CAS  PubMed  Google Scholar 

  45. Maity, P., Shacklady-McAtee, D. M., Yap, G. P. A., Sirianni, E. R. & Watson, M. P. Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: stereospecific formation of diarylethanes via C−N bond activation. J. Am. Chem. Soc. 135, 280–285 (2013)

    Article  CAS  PubMed  Google Scholar 

  46. Lin, B. L., Clough, C. R. & Hillhouse, G. L. Interactions of aziridines with nickel complexes: oxidative-addition and reductive-elimination reactions that break and make C−N bonds. J. Am. Chem. Soc. 124, 2890–2891 (2002)

    Article  CAS  PubMed  Google Scholar 

  47. Huang, C.-Y. & Doyle, A. G. Nickel-catalyzed Negishi alkylations of styrenyl aziridines. J. Am. Chem. Soc. 134, 9541–9544 (2012)

    Article  CAS  PubMed  Google Scholar 

  48. Nielsen, D. K., Huang, C.-Y. & Doyle, A. G. Directed nickel-catalyzed Negishi cross coupling of alkyl aziridines. J. Am. Chem. Soc. 135, 13605–13609 (2013)

    Article  CAS  PubMed  Google Scholar 

  49. Frisch, A. C. & Beller, M. Catalysts for cross-coupling reactions with non-activated alkyl halides. Angew. Chem. Int. Edn 44, 674–688 (2005)

    Article  CAS  Google Scholar 

  50. Hu, X. Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective. Chem. Sci. 2, 1867–1886 (2011)

    Article  CAS  Google Scholar 

  51. Hills, I. D., Netherton, M. R. & Fu, G. C. Toward an improved understanding of the unusual reactivity of Pd0/trialkylphosphane catalysts in cross-couplings of alkyl electrophiles: quantifying the factors that determine the rate of oxidative addition. Angew. Chem. Int. Edn 42, 5749–5752 (2003)

    Article  CAS  Google Scholar 

  52. Netherton, M. R. & Fu, G. C. Nickel-catalyzed cross-couplings of unactivated alkyl halides and pseudohalides with organometallic compounds. Adv. Synth. Catal. 346, 1525–1532 (2004)

    Article  CAS  Google Scholar 

  53. Ishiyama, T., Abe, S., Miyaura, N. & Suzuki, A. Palladium-catalyzed alkyl-alkyl cross-coupling reaction of 9-alkyl-9-BBN derivatives with iodoalkanes possessing β-hydrogens. Chem. Lett. 21, 691–694 (1992)

    Article  Google Scholar 

  54. Devasagayaraj, A., Stüdemann, T. & Knochel, P. A new nickel-catalyzed cross-coupling reaction between sp3 carbon centers. Angew. Chem. Int. Edn Engl. 34, 2723–2725 (1996)

    Article  Google Scholar 

  55. Giovannini, R. & Knochel, P. Ni(II)-catalyzed cross-coupling between polyfunctionalized arylzinc derivatives and primary alkyl iodides. J. Am. Chem. Soc. 120, 11186–11187 (1998)

    Article  CAS  Google Scholar 

  56. Terao, J., Watanabe, H., Ikumi, A., Kuniyasu, H. & Kambe, N. Nickel-catalyzed cross-coupling reaction of Grignard reagents with alkyl halides and tosylates: remarkable effect of 1,3-butadienes. J. Am. Chem. Soc. 124, 4222–4223 (2002)

    Article  CAS  PubMed  Google Scholar 

  57. Zhou, J. & Fu, G. C. Cross-couplings of unactivated secondary alkyl halides: room-temperature nickel-catalyzed Negishi reactions of alkyl bromides and iodides. J. Am. Chem. Soc. 125, 14726–14727 (2003)Reports the first secondary C( sp3)–C( sp3) cross-coupling.

    Article  CAS  PubMed  Google Scholar 

  58. Zhou, J. & Fu, G. C. Suzuki cross-couplings of unactivated secondary alkyl bromides and iodides. J. Am. Chem. Soc. 126, 1340–1341 (2004)

    Article  CAS  PubMed  Google Scholar 

  59. Powell, D. A. & Fu, G. C. Nickel-catalyzed cross-couplings of organosilicon reagents with unactivated secondary alkyl bromides. J. Am. Chem. Soc. 126, 7788–7789 (2004)

    Article  CAS  PubMed  Google Scholar 

  60. Powell, D. A., Maki, T. & Fu, G. C. Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents. J. Am. Chem. Soc. 127, 510–511 (2005)

    Article  CAS  PubMed  Google Scholar 

  61. Saito, B. & Fu, G. C. Alkyl–alkyl Suzuki cross-couplings of unactivated secondary alkyl halides at room temperature. J. Am. Chem. Soc. 129, 9602–9603 (2007)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. Dudnik, A. S. & Fu, G. C. Nickel-catalyzed coupling reactions of alkyl electrophiles, including unactivated tertiary halides, to generate carbon–boron bonds. J. Am. Chem. Soc. 134, 10693–10697 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  63. Zultanski, S. L. & Fu, G. C. Nickel-catalyzed carbon–carbon bond-forming reactions of unactivated tertiary alkyl halides: Suzuki arylations. J. Am. Chem. Soc. 135, 624–627 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  64. Rudolph, A. & Lautens, M. Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions. Angew. Chem. Int. Edn 48, 2656–2670 (2009)

    Article  CAS  Google Scholar 

  65. Jones, G. D. et al. Ligand redox effects in the synthesis, electronic structure, and reactivity of an alkyl–alkyl cross-coupling catalyst. J. Am. Chem. Soc. 128, 13175–13183 (2006)

    Article  CAS  PubMed  Google Scholar 

  66. Lipschutz, M. I., Yang, X., Chatterjee, R. & Tilley, T. D. A structurally rigid bis(amido) ligand framework in low-coordinate Ni(I), Ni(II), and Ni(III) analogues provides access to a Ni(III) methyl complex via oxidative addition. J. Am. Chem. Soc. 135, 15298–15301 (2013)

    Article  CAS  PubMed  Google Scholar 

  67. Csok, Z., Vechorkin, O., Harkins, S. B., Scopelliti, R. & Hu, X. Nickel complexes of a pincer NN2 ligand: multiple carbon–chloride activation of CH2Cl2 and CHCl3 leads to selective carbon–carbon bond formation. J. Am. Chem. Soc. 130, 8156–8157 (2008)

    Article  CAS  PubMed  Google Scholar 

  68. Vechorkin, O. & Hu, X. Nickel-catalyzed cross-coupling of non-activated and functionalized alkyl halides with alkyl Grignard reagents. Angew. Chem. Int. Edn 48, 2937–2940 (2009)

    Article  CAS  Google Scholar 

  69. Vechorkin, O., Barmaz, D., Proust, V. & Hu, X. Ni-catalyzed Sonogashira coupling of nonactivated alkyl halides: orthogonal functionalization of alkyl iodides, bromides, and chlorides. J. Am. Chem. Soc. 131, 12078–12079 (2009)

    Article  CAS  PubMed  Google Scholar 

  70. Breitenfeld, J., Ruiz, J., Wodrich, M. D. & Hu, X. Bimetallic oxidative addition involving radical intermediates in nickel-catalyzed alkyl–alkyl Kumada coupling reactions. J. Am. Chem. Soc. 135, 12004–12012 (2013)

    Article  CAS  PubMed  Google Scholar 

  71. Fischer, C. & Fu, G. C. Asymmetric nickel-catalyzed Negishi cross-couplings of secondary α-bromo amides with organozinc reagents. J. Am. Chem. Soc. 127, 4594–4595 (2005)

    Article  CAS  PubMed  Google Scholar 

  72. Zultanski, S. L. & Fu, G. C. Catalytic asymmetric γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings. J. Am. Chem. Soc. 133, 15362–15364 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  73. Gong, H. & Gagné, M. R. Diastereoselective Ni-catalyzed Negishi cross-coupling approach to saturated, fully oxygenated C-alkyl and C-aryl glycosides. J. Am. Chem. Soc. 130, 12177–12183 (2008)

    Article  CAS  PubMed  Google Scholar 

  74. Son, S. & Fu, G. C. Nickel-catalyzed asymmetric Negishi cross-couplings of secondary allylic chlorides with alkylzincs. J. Am. Chem. Soc. 130, 2756–2757 (2008)

    Article  CAS  PubMed  Google Scholar 

  75. Everson, D. A., Shrestha, R. & Weix, D. J. Nickel-catalyzed reductive cross-coupling of aryl halides with alkyl halides. J. Am. Chem. Soc. 132, 920–921 (2010)

    Article  CAS  PubMed  Google Scholar 

  76. Everson, D. A., Jones, B. A. & Weix, D. J. Replacing conventional carbon nucleophiles with electrophiles: nickel-catalyzed reductive alkylation of aryl bromides and chlorides. J. Am. Chem. Soc. 134, 6146–6159 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  77. Biswas, S. & Weix, D. J. Mechanism and selectivity in nickel-catalyzed cross-electrophile coupling of aryl halides with alkyl halides. J. Am. Chem. Soc. 135, 16192–16197 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  78. Cherney, A. H., Kadunce, N. T. & Reisman, S. E. Catalytic asymmetric reductive acyl cross-coupling: synthesis of enantioenriched acyclic α,α-disubstituted ketones. J. Am. Chem. Soc. 135, 7442–7445 (2013)

    Article  CAS  PubMed  Google Scholar 

  79. Kleiman, J. P. & Dubeck, M. The preparation of cyclopentadienyl [o-(phenylazo)phenyl]nickel. J. Am. Chem. Soc. 85, 1544–1545 (1963)

    Article  CAS  Google Scholar 

  80. Muto, K., Yamaguchi, J. & Itami, K. Nickel-catalyzed C–H/C–O coupling of azoles with phenol derivatives. J. Am. Chem. Soc. 134, 169–172 (2012)

    Article  CAS  PubMed  Google Scholar 

  81. Amaike, K., Muto, K., Yamaguchi, J. & Itami, K. Decarbonylative C–H coupling of azoles and aryl esters: unprecedented nickel catalysis and application to the synthesis of muscoride A. J. Am. Chem. Soc. 134, 13573–13576 (2012)

    Article  CAS  PubMed  Google Scholar 

  82. Muto, K., Yamaguchi, J., Lei, A. & Itami, K. Isolation, structure, and reactivity of an arylnickel(II) pivalate complex in catalytic C–H/C–O biaryl coupling. J. Am. Chem. Soc. 135, 16384–16387 (2013)

    Article  CAS  PubMed  Google Scholar 

  83. Shiota, H., Ano, Y., Aihara, Y., Fukumoto, Y. & Chatani, N. Nickel-catalyzed chelation-assisted transformations involving ortho C–H bond activation: regioselective oxidative cycloaddition of aromatic amides to alkynes. J. Am. Chem. Soc. 133, 14952–14955 (2011)

    Article  CAS  PubMed  Google Scholar 

  84. Aihara, Y. & Chatani, N. Nickel-catalyzed direct alkylation of C–H bonds in benzamides and acrylamides with functionalized alkyl halides via bidentate-chelation assistance. J. Am. Chem. Soc. 135, 5308–5311 (2013)

    Article  CAS  PubMed  Google Scholar 

  85. Aihara, Y. & Chatani, N. Nickel-catalyzed direct arylation of C(sp3)–H bonds in aliphatic amides via bidentate-chelation assistance. J. Am. Chem. Soc. 136, 898–901 (2014)

    Article  CAS  PubMed  Google Scholar 

  86. Oestreich M., ed. The Mizoroki–Heck Reaction (Wiley, 2009)

  87. Cabri, W. & Candiani, I. Recent developments and new perspectives in the Heck reaction. Acc. Chem. Res. 28, 2–7 (1995)

    Article  CAS  Google Scholar 

  88. Gøgsig, T. M. et al. Mild and efficient nickel-catalyzed Heck reactions with electron-rich olefins. J. Am. Chem. Soc. 134, 443–452 (2012)

    Article  CAS  PubMed  Google Scholar 

  89. Matsubara, R., Gutierrez, A. C. & Jamison, T. F. Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins. J. Am. Chem. Soc. 133, 19020–19023 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  90. Standley, E. A. & Jamison, T. F. Simplifying nickel(0) catalysis: an air-stable nickel precatalyst for the internally selective benzylation of terminal alkenes. J. Am. Chem. Soc. 135, 1585–1592 (2013)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  91. Tasker, S. Z., Gutierrez, A. C. & Jamison, T. F. Nickel-catalyzed Mizoroki–Heck reaction of aryl sulfonates and chlorides with electronically unbiased terminal olefins: high selectivity for branched products. Angew. Chem. Int. Edn 53, 1858–1861 (2014)

    Article  CAS  Google Scholar 

  92. Ng, S.-Z., Ho, C.-Y., Schleicher, K. D. & Jamison, T. F. Nickel-catalyzed coupling reactions of alkenes. Pure Appl. Chem. 80, 929–939 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  93. Moslin, R. M., Miller-Moslin, K. & Jamison, T. F. Regioselectivity and enantioselectivity in nickel-catalysed reductive coupling reactions of alkynes. Chem. Commun. 4441–4449 (2007)

  94. Herath, A., Li, W. & Montgomery, J. Fully intermolecular nickel-catalyzed three-component couplings via internal redox. J. Am. Chem. Soc. 130, 469–471 (2008)

    Article  CAS  PubMed  Google Scholar 

  95. Beaver, M. G. & Jamison, T. F. Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes. Org. Lett. 13, 4140–4143 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  96. Miller, K. M. & Jamison, T. F. Ligand-switchable directing effects of tethered alkenes in nickel-catalyzed additions to alkynes. J. Am. Chem. Soc. 126, 15342–15343 (2004)

    Article  CAS  PubMed  Google Scholar 

  97. Moslin, R. M. & Jamison, T. F. Mechanistic implications of nickel-catalyzed reductive coupling of aldehydes and chiral 1,6-enynes. Org. Lett. 8, 455–458 (2006)

    Article  CAS  PubMed  Google Scholar 

  98. Malik, H. A., Sormunen, G. J. & Montgomery, J. A general strategy for regiocontrol in nickel-catalyzed reductive couplings of aldehydes and alkynes. J. Am. Chem. Soc. 132, 6304–6305 (2010)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  99. Liu, P., Montgomery, J. & Houk, K. N. Ligand steric contours to understand the effects of N-heterocyclic carbene ligands on the reversal of regioselectivity in Ni-catalyzed reductive couplings of alkynes and aldehydes. J. Am. Chem. Soc. 133, 6956–6959 (2011)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  100. Firmansjah, L. & Fu, G. C. Intramolecular Heck reactions of unactivated alkyl halides. J. Am. Chem. Soc. 129, 11340–11341 (2007)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the NIGMS (GM62755) and the NSF (Graduate Research Fellowship to S.Z.T. and E.A.S.).

Author information

Authors and Affiliations

Authors

Contributions

S.Z.T. and E.A.S. worked together to outline and write the content, and T.F.J. helped edit the manuscript, references and figures.

Corresponding author

Correspondence to Timothy F. Jamison.

Ethics declarations

Competing interests

The authors declare no competing financial interests.

PowerPoint slides

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tasker, S., Standley, E. & Jamison, T. Recent advances in homogeneous nickel catalysis. Nature 509, 299–309 (2014). https://doi.org/10.1038/nature13274

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/nature13274

This article is cited by

Comments

By submitting a comment you agree to abide by our Terms and Community Guidelines. If you find something abusive or that does not comply with our terms or guidelines please flag it as inappropriate.

Search

Quick links

Nature Briefing

Sign up for the Nature Briefing newsletter — what matters in science, free to your inbox daily.

Get the most important science stories of the day, free in your inbox. Sign up for Nature Briefing