Citation: WU Qiang, KANG Chuanqing, GAO Lianxun. Advances in Olefin Isomerization Reactions Catalyzed by the First-row Transition Metals[J]. Chinese Journal of Applied Chemistry, ;2017, 34(1): 25-39. doi: 10.11944/j.issn.1000-0518.2017.01.160258 shu

Advances in Olefin Isomerization Reactions Catalyzed by the First-row Transition Metals

WU Qiang ^a,b ,
KANG Chuanqing ^a,*,, ,
GAO Lianxun ^a

a.
State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: KANG Chuanqing, kangcq@ciac.ac.cn
Received Date: 21 June 2016
Revised Date: 4 August 2016
Accepted Date: 29 August 2016

Fund Project: Supported by Jilin Technology R&D Program No. 20140203003GX

Figures(26)

Transition-metal-catalyzed olefin isomerization has played a crucial role in the synthesis of organic compounds, commodity chemicals, natural products, and petroleum feedstocks. Although noble metals such as Ru, Rh and Ir as catalysts for the conversions have made dramatic achievements, the disadvantages of the rare resource, high cost, and poisoning products have limited its wide application in the synthesis. Due to the abundant supply, low cost and easy removal from the final products, the first-row transition metals have attracted much attention from the chemists and have proven to be very promising with respect to the development of more sustainable catalytic system in olefin isomerizaton. This review summaried the advances in olefin isomerization catalyzed by iron, cobalt, nickel in the past years and illustrates the differences among different catalytic systems in catalytic activity, regio- and stereo-selectivity, and substrate scope. Recent developments in the olefin isomerization catalyzed by the first-row metals have proven to be very promising and effective. The reaction mechanism was discussed to have deep insight into the isomerization. The mechanism of olefin isomerization was illustrated clearly in the reported articles through intermolecular or intramolecular hydrogen shift, and the stereoselectivity and regioselectivity in different catalytic system was still worthy of further investigations. Further studies in the field to solve the challenges in high catalytic activity, stereoselectivity, and wide substrate scopes would bring the isomerization into better prospect.
- olefin isomerization,
- transition metals,
- regioselectivity,
- stereoselectivity,
- catalysis
1. [1]
  Sakthivel A, Mahato N R, Baskaran T. Molybdenum Carbonyl Grafted onto Silicate Intercalated Cobalt Aluminum Hydrotalcite:A New Potential Catalyst for the Hydroformylation of Octene[J]. Catal Commun, 2015,65:55-61. doi: 10.1016/j.catcom.2015.02.024
2. [2]
  Zhang L, Zuo Z, Leng X. A Cobalt-catalyzed Alkene Hydroboration with Pinacolborane[J]. Angew Chem Int Ed, 2014,53(10):2696-2700. doi: 10.1002/anie.201310096
3. [3]
  Palmer W N, Diao T, Pappas I. High-activity Cobalt Catalysts for Alkene Hydroboration with Electronically Responsive Terpyridine and α-Diimine Ligands[J]. ACS Catal, 2014,5(2):622-626.
4. [4]
  Ruddy A J, Sydora O L, Small B L. (N-Phosphinoamidinate) Cobalt-catalyzed Hydroboration:Alkene Isomerization Affords Terminal Selectivity[J]. Chem Eur J, 2014,20(43):13918-13922. doi: 10.1002/chem.v20.43
5. [5]
  Xue M, Li J, Peng J. Effect of Triarylphosphane Ligands on the Rhodium-catalyzed Hydrosilylation of Alkene[J]. Appl Organomet Chem, 2014,28(2):120-126. doi: 10.1002/aoc.3092
6. [6]
  Komine N, Abe M, Suda R. Markovnikov-selective Hydrosilylation of Electron-deficient Alkenes with Arylsilanes Catalyzed by Mono(phosphine)palladium(0)[J]. Organometallics, 2015,34(2):432-437. doi: 10.1021/om500964g
7. [7]
  Schmidt A, Nodling A R, Hilt G. An Alternative Mechanism for the Cobalt-catalyzed Isomerization of Terminal Alkenes to (Z)-2-Alkenes[J]. Angew Chem Int Ed, 2015,54(3):801-804. doi: 10.1002/anie.201409902
8. [8]
  Lee W C, Wang C H, Lin Y H. Tandem Isomerization and C-H Activation:Regioselective Hydroheteroarylation of Allylarenes[J]. Org Lett, 2013,15(20):5358-5361. doi: 10.1021/ol402644y
9. [9]
  Donohoe T J, O'Riordan T J, Rosa C P. Ruthenium-catalyzed Isomerization of Terminal Olefins:Applications to Synthesis[J]. Angew Chem Int Ed, 2009,48(6):1014-1017. doi: 10.1002/anie.v48:6
10. [10]
  Seayad A, Ahmed M, Klein H. Internal Olefins to Linear Amines[J]. Science, 2002,297(5587):1676-1678. doi: 10.1126/science.1074801
11. [11]
  Huang Y H, Dass R I, Xing Z L. Double Perovskites as Anode Materials for Solid-oxide Fuel Cells[J]. Science, 2006,312(5771):254-257. doi: 10.1126/science.1125877
12. [12]
  Biswas S, Huang Z, Choliy Y. Olefin Isomerization by Iridium Pincer Catalysts. Experimental Evidence for an η³-Allyl Pathway and an Unconventional Mechanism Predicted by DFT Calculations[J]. J Am Chem Soc, 2012,134(32):13276-13295. doi: 10.1021/ja301464c
13. [13]
  Wu Q, Jin R, Kang C. Ni-catalyzed Cross Coupling of Aryl Grignard Reagents with Aryl Halides in a Nonpolar Solvent and an Efficient Synthesis of Biaryls Under Neat Conditions[J]. Chem Res Chinese Univ, 2016,32(1):55-61. doi: 10.1007/s40242-016-5261-0
14. [14]
  Han F S. Transition-metal-catalyzed Suzuki-Miyaura Cross-coupling Reactions:A Remarkable Advance from Palladium to Nickel Catalysts[J]. Chem Soc Rev, 2013,42(12):5270-5298. doi: 10.1039/c3cs35521g
15. [15]
  Lim H J, Smith C R, RajanBabu T. Facile Pd(Ⅱ)- and Ni(Ⅱ)-Catalyzed Isomerization of Terminal Alkenes into 2-Alkenes[J]. J Org Chem, 2009,74(12):4565-4572. doi: 10.1021/jo900180p
16. [16]
  Gauthier D, Lindhardt A T, Olsen E P. In Situ Generated Bulky Palladium Hydride Complexes as Catalysts for the Efficient Isomerization of Olefins. Selective Transformation of Terminal Alkenes to 2-Alkenes[J]. J Am Chem Soc, 2010,132(23):7998-8009. doi: 10.1021/ja9108424
17. [17]
  Alphonse F A, Yudin A K. Rhodium-catalyzed Stereoselective Formation of Z-Enamines from Allylaziridines[J]. J Am Chem Soc, 2006,128(36):11754-11755. doi: 10.1021/ja0632557
18. [18]
  Tsang D S, Yang S, Alphonse F A. Stereoselective Isomerisation of N-Allyl Aziridines into Geometrically Stable Z Enamines by Using Rhodium Hydride Catalysis[J]. Chem Eur J, 2008,14(3):886-894. doi: 10.1002/(ISSN)1521-3765
19. [19]
  Zhuo L G, Yao Z K, Yu Z X. Synthesis of Z-Alkenes from Rh(Ⅰ)-Catalyzed Olefin Isomerization of β,γ-Unsaturated Ketones[J]. Org Lett, 2013,15(18):4634-4637. doi: 10.1021/ol401607c
20. [20]
  Arisawa M, Terada Y, Takahashi K. Development of Isomerization and Cycloisomerization with Use of a Ruthenium Hydride with N-Heterocyclic Carbene and Its Application to the Synthesis of Heterocycles[J]. J Org Chem, 2006,71(11):4255-4261. doi: 10.1021/jo060308u
21. [21]
  Hanessian S, Giroux S, Larsson A. Efficient Allyl to Propenyl Isomerization in Functionally Diverse Compounds with a Thermally Modified Grubbs Second-generation Catalyst[J]. Org Lett, 2006,8(24):5481-5484. doi: 10.1021/ol062167o
22. [22]
  Sharma S K, Srivastava V K, Jasra R V. Selective Double Bond Isomerization of Allyl Phenyl Ethers Catalyzed by Ruthenium Metal Complexes[J]. J Mol Catal A:Chem, 2006,245(1):200-209.
23. [23]
  Grotjahn D B, Larsen C R, Gustafson J L. Extensive Isomerization of Alkenes Using a Bifunctional Catalyst:An Alkene Zipper[J]. J Am Chem Soc, 2007,129(31):9592-9593. doi: 10.1021/ja073457i
24. [24]
  Larsen C R, Grotjahn D B. Stereoselective Alkene Isomerization over One Position[J]. J Am Chem Soc, 2012,134(25):10357-10360. doi: 10.1021/ja3036477
25. [25]
  Larsen C R, Erdogan G, Grotjahn D B. General Catalyst Control of the Monoisomerization of 1-Alkenes to Trans-2-alkenes[J]. J Am Chem Soc, 2014,136(4):1226-1229. doi: 10.1021/ja411438d
26. [26]
  Chianese A R, Shaner S E, Tendler J A. Iridium Complexes of Bulky CCC-pincer N-Heterocyclic Carbene Ligands:Steric Control of Coordination Number and Catalytic Alkene Isomerization[J]. Organometallics, 2012,31(21):7359-7367. doi: 10.1021/om300468d
27. [27]
  Knapp S M M, Shaner S E, Kim D. Mechanistic Studies of Alkene Isomerization Catalyzed by CCC-pincer Complexes of Iridium[J]. Organometallics, 2014,33(2):473-484. doi: 10.1021/om400786r
28. [28]
  Yamamoto Y, Miyairi T, Ohmura T. Synthesis of Chiral Esters of (E)-3-(Silyloxy)-2-propenylboronic Acid via the Iridium-catalyzed Isomerization of the Double Bond[J]. J Org Chem, 1999,64(1):296-298. doi: 10.1021/jo9814288
29. [29]
  Sivaramakrishna A, Mushonga P, Rogers I L. Selective Isomerization of 1-Alkenes by Binary Metal Carbonyl Compounds[J]. Polyhedron, 2008,27(7):1911-1916. doi: 10.1016/j.poly.2008.02.026
30. [30]
  Göttker-Schnetmann I, White P, Brookhart M. Iridium Bis(phosphinite) p-XPCP Pincer Complexes:Highly Active Catalysts for the Transfer Dehydrogenation of Alkanes[J]. J Am Chem Soc, 2004,126(6):1804-1811. doi: 10.1021/ja0385235
31. [31]
  Chen C, Dugan T R, Brennessel W W. Z-Selective Alkene Isomerization by High-spin Cobalt(Ⅱ) Complexes[J]. J Am Chem Soc, 2014,136(3):945-955. doi: 10.1021/ja408238n
32. [32]
  Courchay F C, Sworen J C, Ghiviriga I. Understanding Structural Isomerization During Ruthenium-catalyzed Olefin Metathesis:A Deuterium Labeling Study[J]. Organometallics, 2006,25(26):6074-6086. doi: 10.1021/om0509894
33. [33]
  Morrill T C, D'Souza C A. Efficient Hydride-assisted Isomerization of Alkenes via Rhodium Catalysis[J]. Organometallics, 2003,22(8):1626-1629. doi: 10.1021/om0207358
34. [34]
  Larionov E, Lin L, Guénée L. Scope and Mechanism in Palladium-catalyzed Isomerizations of Highly Substituted Allylic, Homoallylic, and Alkenyl Alcohols[J]. J Am Chem Soc, 2014,136(48):16882-16894. doi: 10.1021/ja508736u
35. [35]
  Correa A, Garcia Mancheno O, Bolm C. Iron-catalysed Carbon-heteroatom and Heteroatom-eteroatom Bond Forming Processes[J]. Chem Soc Rev, 2008,37(6):1108-1117. doi: 10.1039/b801794h
36. [36]
  Bauer E B. Recent Advances in Iron Catalysis in Organic Synthesis[J]. Curr Org Chem, 2008,12(16):1341-1369. doi: 10.2174/138527208786241556
37. [37]
  Czaplik W M, Mayer M, Cvengro J. Coming of Age:Sustainable Iron-catalyzed Cross-coupling Reactions[J]. ChemSusChem, 2009,2(5):396-417. doi: 10.1002/cssc.v2:5
38. [38]
  Frankel E N, Emken E A, Davison V L. Isomerization of Unsaturated Fatty Esters by Iron Pentacarbonyl. Preparation of Iron Tricarbonyl Complexes of Polyunsaturated Fats[J]. J Am Oil Chem Soc, 1966,43(5):307-311. doi: 10.1007/BF02609679
39. [39]
  Casey C P, Cyr C R. Iron Carbonyl Catalyzed Isomerization of 3-Ethyl-1-pentene. Multiple Olefin Isomerizations via a π-Allyl Metal Hydride Intermediate[J]. J Am Chem Soc, 1973,95(7):2248-2253. doi: 10.1021/ja00788a025
40. [40]
  De Pasquale R J. Isomerization of Estragole to Anethole[J]. Synth Commun, 2006,10(3):225-231.
41. [41]
  Tooley P A, Arndt L W, Darensbourg M Y. Olefin Isomerization Catalysis by Heterobimetallic Hydrides, HFeM(CO)₈L^-(M=Cr,Mo,W; L=Co,Pr₃)[J]. J Am Chem Soc, 1985,107(8):2422-2427. doi: 10.1021/ja00294a037
42. [42]
  Reddy M R, Periasamy M. Isomerization of 1-Alkenes Using the Na₂Fe(Co)₄/CuCl and Na₂Fe(Co)₄/BrCH₂CH₂Br Reagent Systems[J]. J Organomet Chem, 1995,491(1/2):263-266.
43. [43]
  Crivello J V, Kong S Q. Efficient Isomerization of Allyl Ethers and Related Compounds Using Pentacarbonyliron[J]. J Org Chem, 1998,63(19):6745-6748. doi: 10.1021/jo980581z
44. [44]
  Jennerjahn R, Jackstell R, Piras I. Benign Catalysis with Iron:Unique Selectivity in Catalytic Isomerization Reactions of Olefins[J]. Chem Sus Chem, 2012,5(4):734-739. doi: 10.1002/cssc.v5.4
45. [45]
  Mayer M, Welther A, Jacobi von Wangelin A. Iron-catalyzed Isomerizations of Olefins[J]. Chem Cat Chem, 2011,3(10):1567-1571.
46. [46]
  Karapinka G L, Orchin M. The Stoichiometric Hydroformylation of 1-Pentene at Room Conditions1[J]. J Org Chem, 1961,26(11):4187-4190. doi: 10.1021/jo01069a001
47. [47]
  Roos L, Orchin M. Allylbenzene Isomerization Catalyzed by Deuteriocobalt Tetracarbonyl[J]. J Am Chem Soc, 1965,87(23):5502-5504.
48. [48]
  McCormack W E, Orchin M. The Cobalt Hydrocarbonyl-catalyzed Isomerization of Allylbenzene[J]. J Organomet Chem, 1977,129(1):127-137. doi: 10.1016/S0022-328X(00)93234-0
49. [49]
  Onishi M, Oishi S, Sakaguchi M. Chemical Reactivities of Coordinatively Unsaturated Hydridotris(Phosphonite) Cobalt(Ⅰ) Species Photogenerated Towards Allylic and Related Compounds[J]. Bull Chem Soc Jpn, 1986,59(12):3925-3930. doi: 10.1246/bcsj.59.3925
50. [50]
  Onishi M, Hiraki K, Ishida Y. Facile Electrogeneration of a 17-Electron Species from an Inert Hydridophosphonitecobalt(Ⅰ) for Catalytic Double-Bond Migration of 3-Phenylpropene[J]. Chem Lett, 1986,15(3):333-336. doi: 10.1246/cl.1986.333
51. [51]
  Satyanarayana N, Periasamy M. Isomerization of Olefins Catalysed by a CoCl₂/Ph₃P/NaBH₄ System[J]. J Organomet Chem, 1987,319(1):113-117. doi: 10.1016/0022-328X(87)80353-4
52. [52]
  Kobayashi T, Ohmiya H, Yorimitsu H. Cobalt-catalyzed Regioselective Dehydrohalogenation of Alkyl Halides with Dimethylphenylsilylmethylmagnesium Chloride[J]. J Am Chem Soc, 2008,130(34):11276-11277. doi: 10.1021/ja804277x
53. [53]
  Kobayashi T, Yorimitsu H, Oshima K. Cobalt-catalyzed Isomerization of 1-Alkenes to (E)-2-Alkenes with Dimethylphenylsilylmethylmagnesium Chloride and Its Application to the Stereoselective Synthesis of (E)-Alkenylsilanes[J]. Chem Asian J, 2009,4(7):1078-1083. doi: 10.1002/asia.v4:7
54. [54]
  Bohn M A, Schmidt A, Hilt G. Cobalt-catalyzed 1,4-Hydrobutadienylation of 1-Aryl-1,3-dienes with 2,3-Dimethyl-1,3-butadiene[J]. Angew Chem Int Ed, 2011,50(41):9689-9693. doi: 10.1002/anie.201103613
55. [55]
  Punner F, Schmidt A, Hilt G. Up the Hill:Selective Double-bond Isomerization of Terminal 1,3-Dienes Towards Z-1,3-Dienes or 2Z,4E-Dienes[J]. Angew Chem Int Ed, 2012,51(5):1270-1273. doi: 10.1002/anie.201107512
56. [56]
  Schmidt A, Hilt G. Unprecedented Cobalt-catalyzed Isomerization Reactions to Single Skipped 2,4,7-Trienes Applied in the Synthesis of Urushiol[J]. Chem Asian J, 2014,9(9):2407-2410. doi: 10.1002/asia.201402323
57. [57]
  Crossley S W, Barabe F, Shenvi R A. Simple, Chemoselective, Catalytic Olefin Isomerization[J]. J Am Chem Soc, 2014,136(48):16788-16791. doi: 10.1021/ja5105602
58. [58]
  Cramer R, Lindsey Jr R. The Mechanism of Isomerization of Olefins with Transition Metal Catalysts[J]. J Am Chem Soc, 1966,88(15):3534-3544. doi: 10.1021/ja00967a013
59. [59]
  Tolman C A. Chemistry of Tetrakis(triethyl phosphite)nickel Hydride, HNi[P(OEt)₃]⁴⁺.IV.Mechanism of Olefin Isomerization[J]. J Am Chem Soc, 1972,94(9):2994-2999. doi: 10.1021/ja00764a016
60. [60]
  Bontempelli G, Daniele S, Schiavon G. An Electroanalytical Investigation of the Olefin Isomerization Reaction Promoted by Electrogenerated Cationic Nickel(Ⅰ) Complexes[J]. Trans Met Chem, 1987,12(4):292-295. doi: 10.1007/BF01024015
61. [61]
  Bontempelli G, Fiorani M, Daniele S. An Electroanalytical Investigation on the Olefin Isomerization Reaction Promoted by Electrogenerated Cationic Nickel Hydrides[J]. J Mol Catal, 1987,40(1):9-21. doi: 10.1016/0304-5102(87)80002-0
62. [62]
  Bricout H, Mortreux A, Monflier E. Isomerization of Olefins in a Two-phase System by Homogeneous Water-soluble Nickel Complexes[J]. J Organomet Chem, 1998,553(1):469-471.
63. [63]
  Kuntz E G, Godard G, Basset J M. Nickel(0)-TPPTS-Cyanide Complex in Water. An Efficient and Flexible Catalyst for the Isomerisation of Olefinic Compounds at Room Temperature[J]. Oil Gas Sci Technol-Revue de l'IFP, 2007,62(6):781-785. doi: 10.2516/ogst:2007036
64. [64]
  Wille A, Tomm S, Frauenrath H. A Highly Z-Selective Isomerization(double-bond migration) Procedure for Allyl Acetals and Allyl Ethers Mediated by Nickel Complexes[J]. Synthesis, 1998,1998(3):305-308. doi: 10.1055/s-1998-2028
65. [65]
  Wang L, Liu C, Bai R. Easy Access to Enamides:A Mild Nickel-catalysed Alkene Isomerization of Allylamides[J]. Chem Commun, 2013,49(72):7923-7925. doi: 10.1039/c3cc43875a
66. [66]
  Weber F, Schmidt A, Rose P. Double-bond Isomerization:Highly Reactive Nickel Catalyst Applied in the Synthesis of the Pheromone (9z,12z)-Tetradeca-9,12-dienyl Acetate[J]. Org Lett, 2015,17(12):2952-2955. doi: 10.1021/acs.orglett.5b01230
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