Advances in Nickel-Catalyzed Cycloaddition Reactions To Construct Carbocycles and Heterocycles

Accounts of Chemical Research

Volumn 48, Issue 8, 2015, Pages 2354-2365

  Thakur, Ashish ^a   Louie, Janis ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; CARBENE; CARBON DIOXIDE; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOCYANIC ACID DERIVATIVE; KETONE; METHANE; NICKEL; NITRILE; PYRIDONE DERIVATIVE; PYRONE DERIVATIVE; TROPOLONE; TROPONE;

ANALOGS AND DERIVATIVES; CATALYSIS; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

CARBON DIOXIDE; CATALYSIS; CYCLOADDITION REACTION; CYCLOPROPANES; DIYNES; HETEROCYCLIC COMPOUNDS; ISOCYANATES; KETONES; METHANE; NICKEL; NITRILES; PYRIDONES; PYRONES; TROPOLONE;

EID: 84939498301     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/acs.accounts.5b00054     Document Type: Article

References (39)

1. Hoberg, H.; Oster, B. W. Nickelaverbindungen als zwischenkomplexe der [2 + 2+2′]-cycloaddition von alkinen mit isocyanaten zu 2-pyridonen J. Organomet. Chem. 1983, 252, 359-364 and references therein 10.1016/S0022-328X(00)99836-X
2. Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. Nickel(0)-catalyzed cycloaddition of diynes and carbon dioxide to give bicyclic.alpha.-pyrones J. Org. Chem. 1988, 53, 3140-3145 10.1021/jo00249a003
3. Saito, S.; Nakagawa, S.; Koizumi, T.; Hirayama, K.; Yamamoto, Y. Nickel-Mediated Regio- and Chemoselective Carboxylation of Alkynes in the Presence of Carbon Dioxide J. Org. Chem. 1999, 64, 3975-3978 and references therein 10.1021/jo982443f
4. Hartwig, J. F. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, pp 1097-1106.
5. Leitner, W. Carbon Dioxide as a Raw Material: The Synthesis of Formic Acid and Its Derivatives from CO2 Angew. Chem., Int. Ed. Engl. 1995, 34, 2207-2221 10.1002/anie.199522071
6. Chopade, P. R.; Louie, J. [2 + 2+2] Cycloaddition Reactions Catalyzed by Transition Metal Complexes Adv. Synth. Catal. 2006, 348, 2307-2327 10.1002/adsc.200600325
7. Louie, J. Transition Metal Catalyzed Reactions of Carbon Dioxide and Other Heterocumulenes Curr. Org. Chem. 2005, 9, 605-623 10.2174/1385272053765033
8. Yeung, C. S.; Dong, V. M. Catalytic Making C-C Bonds from Carbon Dioxide via Transition-Metal Catalysis Top. Catal. 2014, 57, 1342-1350 10.1007/s11244-014-0301-9
9. Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO2 and Diynes J. Am. Chem. Soc. 2002, 124, 15188-15189 10.1021/ja027438e
10. Tekavec, T. N.; Arif, A. M.; Louie, J. Regioselectivity in nickel(0) catalyzed cycloadditions of carbon dioxide with diynes Tetrahedron 2004, 60, 7431-7437 10.1016/j.tet.2004.06.025
11. Kumar, P.; Louie, J. Nickel-Mediated [2 + 2 + 2] Cycloaddition. Transition-Metal-Mediated Aromatic Ring Construction; Wiley, Inc.: Hoboken, NJ, 2013; Chapter 2, pp 37-69 and references therein.
12. Earl, R. A.; Vollhardt, K. P. C. The preparation of 2(1H)-pyridinones and 2,3-dihydro-5(1H)-indolizinones via transition metal mediated cocyclization of alkynes and isocyanates. A novel construction of the antitumor agent camptothecin J. Org. Chem. 1984, 49, 4786-4800 10.1021/jo00199a009
13. Yamamoto, Y.; Takagishi, H.; Itoh, K. Ruthenium(II)-Catalyzed Cycloaddition of 1,6-Diynes with Isocyanates Leading to Bicyclic Pyridones Org. Lett. 2001, 3, 2117-2119 10.1021/ol016082t
14. Duong, H. A.; Cross, M. J.; Louie, J. Nickel-Catalyzed Cycloaddition of Alkynes and Isocyanates J. Am. Chem. Soc. 2004, 126, 11438-11439 10.1021/ja046477i
15. Duong, H. A.; Louie, J. Regioselectivity in nickel(0)/phosphine catalyzed cycloadditions of alkynes and isocyanates J. Organomet. Chem. 2005, 690, 5098-5104 10.1016/j.jorganchem.2005.03.027
16. Duong, H. A.; Louie, J. A nickel(0) catalyzed cycloaddition of alkynes and isocyanates that affords pyrimidine-diones Tetrahedron 2006, 62, 7552-7559 10.1016/j.tet.2006.03.119
17. D'Souza, B. R.; Louie, J. Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates Org. Lett. 2009, 11, 4168-4171 10.1021/ol901703t
18. Takahashi, T.; Tsai, F. Y.; Kotora, M. Selective Formation of Substituted Pyridines from Two Different Alkynes and a Nitrile: Novel Coupling Reaction of Azazirconacyclopentadienes with Alkynes J. Am. Chem. Soc. 2000, 122, 4994-4995 10.1021/ja000474y
19. Eisch, J. J.; Ma, X.; Han, K. I.; Gitua, J. N.; Kruger, C. Mechanistic Comparison of the Nickel(0)-Catalyzed Homo-Oligomerization and Co-Oligomerization of Alkynes and Nitriles Eur. J. Inorg. Chem. 2001, 2001, 77-88 10.1002/1099-0682(20011)2001:1<77::AID-EJIC77>3.0.CO;2-G
20. McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. A Nickel-Catalyzed Route to Pyridines J. Am. Chem. Soc. 2005, 127, 5030-5031 10.1021/ja0508931
21. Stolley, R. M.; Maczka, M. T.; Louie, J. Nickel-Catalyzed [2 + 2+2] Cycloaddition of Diynes and Cyanamides Eur. J. Org. Chem. 2011, 2011, 3815-3824 10.1002/ejoc.201100428
22. Kumar, P.; Prescher, S.; Louie, J. A Serendipitous Discovery: Nickel Catalyst for the Cycloaddition of Diynes with Unactivated Nitriles Angew. Chem., Int. Ed. 2011, 50, 10694-10698 10.1002/anie.201104475
23. Stolley, R. M.; Duong, H. A.; Thomas, D. R.; Louie, J. The Discovery of [Ni(NHC)RCN]2 Species and Their Role as Cycloaddition Catalysts for the Formation of Pyridines J. Am. Chem. Soc. 2012, 134, 15154-15162 10.1021/ja3075924
24. Stolley, R. M.; Duong, H. A.; Louie, J. Mechanistic Evaluation of the Ni(IPr)2-Catalyzed Cycloaddition of Alkynes and Nitriles To Afford Pyridines: Evidence for the Formation of a Key η1-Ni(IPr)2(RCN) Intermediate Organometallics 2013, 32, 4952-4960 10.1021/om400666k
25. Zhong, Y.; Spahn, N. A.; Stolley, R. M.; Nguyen, M. H.; Louie, J. 3,5-Disubstituted 2-Aminopyridines via Nickel-Catalyzed Cycloaddition of Terminal Alkynes and Cyanamides Synlett 2015, 26, 307-312 10.1055/s-0034-1379500
26. Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. Nickel(0)-catalyzed reaction of diynes with aldehydes J. Am. Chem. Soc. 1988, 110, 8570-8572 10.1021/ja00233a057
27. Yamamoto, Y.; Takagishi, H.; Itoh, K. Ruthenium(II)-Catalyzed [2 + 2 + 2] Cycloaddition of 1,6-Diynes with Tricarbonyl Compounds J. Am. Chem. Soc. 2002, 124, 6844-6845 10.1021/ja0264100
28. Tekevac, T. N.; Louie, J. Nickel-Catalyzed Cycloaddition of Unsaturated Hydrocarbons and Carbonyl Compounds Org. Lett. 2005, 7, 4037-4039 10.1021/ol0515558
29. Tekavec, T. N.; Louie, J. Nickel-Catalyzed Cycloadditions of Unsaturated Hydrocarbons, Aldehydes, and Ketones J. Org. Chem. 2008, 73, 2641-2648 10.1021/jo702508w
30. Tidwell, T. T. Ketenes; Wiley-Interscience: New York, 1995.
31. Kumar, P.; Troast, D. M.; Cella, R.; Louie, J. Ni-Catalyzed Ketene Cycloaddition: A System That Resists the Formation of Decarbonylation Side Products J. Am. Chem. Soc. 2011, 133, 7719-7721 10.1021/ja2007627
32. Liu, H.; Wu, Y.; Zhao, Y.; Li, Z.; Zhang, l.; Yang, W.; Jiang, H.; Jing, C.; Yu, H.; Wang, B.; Xiao, Y.; Guo, H. Metal-Catalyzed [6 + 3] Cycloaddition of Tropone with Azomethine Ylides: A Practical Access to Piperidine-Fused Bicyclic Heterocycles J. Am. Chem. Soc. 2014, 136, 2625-2629 and references therein 10.1021/ja4122268
33. Kumar, P.; Thakur, A.; Hong, X.; Houk, K. N.; Louie, J. Ni(NHC)]-Catalyzed Cycloaddition of Diynes and Tropone: Apparent Enone Cycloaddition Involving an 8π Insertion J. Am. Chem. Soc. 2014, 136, 17844-17851 10.1021/ja5105206
34. Jun, C.-H.; Park, J.-W. Directed C-C Bond Activation by Transition Metal Complexes Top. Organomet. Chem. 2007, 24, 117-143 10.1007/3418-2007-065
35. Murakami, M.; Matsuda, T. Metal-catalysed cleavage of carbon-carbon bonds Chem. Commun. 2011, 47, 1100-1105 10.1039/C0CC02566F
36. Kumar, P.; Louie, J. A Single Step Approach to Piperidines via Ni-Catalyzed β-Carbon Elimination Org. Lett. 2012, 14, 2026-2029 10.1021/ol300534j
37. Ho, K. Y. T.; Aïssa, C. Regioselective Cycloaddition of 3-Azetidinones and 3-Oxetanones with Alkynes through Nickel-Catalysed Carbon-Carbon Bond Activation Chem.-Eur. J. 2012, 18, 3486-3489 10.1002/chem.201200167
38. Kumar, P.; Zhang, K.; Louie, J. An Expeditious Route to Eight-Membered Heterocycles By Nickel-Catalyzed Cycloaddition: Low-Temperature Csp2-Csp3 Bond Cleavage Angew. Chem., Int. Ed. 2012, 51, 8602-8606 10.1002/anie.201203521
39. Thakur, A.; Facer, M. E.; Louie, J. Nickel-Catalyzed Cycloaddition of 1,3-Dienes with 3-Azetidinones and 3-Oxetanones Angew. Chem., Int. Ed. 2013, 52, 12161-12165 10.1002/anie.201306869