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Synthesis of Acrylic Acid Derivatives from CO2 and Ethylene

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Presentation on theme: "Synthesis of Acrylic Acid Derivatives from CO2 and Ethylene"— Presentation transcript:

1 Synthesis of Acrylic Acid Derivatives from CO2 and Ethylene
Xiao Wang, Hui Wang, Yuhan Sun  Chem  Volume 3, Issue 2, Pages (August 2017) DOI: /j.chempr Copyright © 2017 Elsevier Inc. Terms and Conditions

2 Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

3 Figure 1 Buntine's Calculated Free Energy of Intermediates in a Ni(mDBU)2-Facilitated Reaction Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

4 Figure 2 Resulting Complexes in the Early Study of Mo- and W-Assisted CO2-Ethylene Coupling Reactions Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

5 Scheme 1 Synthesis of Acrylate from CO2 and Ethylene
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

6 Scheme 2 Hoberg's CO2-Norbornene Addition Reaction
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

7 Scheme 3 Walther's CO2-Diene Addition Reaction
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

8 Scheme 4 Hoberg's CO2-Ethylene Addition Reaction and the Formation of Nickelalactone Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

9 Scheme 5 Synthesis of Cinnamic Acid from CO2 and Styrene
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

10 Scheme 6 Formation of Walther's Binuclear Ni(I) Complex
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

11 Scheme 7 Hypothetical Catalytic Cycle of Rieger's Methylation of Nickelalactone and Synthesis of Methyl Acrylate Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

12 Scheme 8 Reaction Mechanism with the Ni-TMEDA Complex Proposed by Kühn
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

13 Scheme 9 Proposed Reaction Pathways with the Ni-dtbpe Complex by Limbach and Hoffmann Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

14 Scheme 10 Obtaining the Crystal Structure for the Methylated Nickelalactone Reprinted with permission from Lee et al.38 Copyright 2013 American Chemical Society. Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

15 Scheme 11 Limbach's Catalytic System Consisting of Ni-dtbpe-tBuONa
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

16 Scheme 12 Limbach's Reaction with (BenzP*)nickelalactone as Intermediate Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

17 Scheme 13 Vogt's Reaction Facilitated by Lithium Salt
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

18 Scheme 14 Stabilization Effect by Sodium Cation
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

19 Scheme 15 Acceleration of β-hydride Elimination by an Electron-Deficient Borane Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

20 Scheme 16 The Expected Catalytic Cycle of Bernskoetter's Mo catalysis
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

21 Scheme 17 Formation of Carbonylation Products by Bernskoetter's Mo-tetrahydride Complex Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

22 Scheme 18 Preparation of a W complex and the Formation-Isomerization of the Oxidative Addition Product Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

23 Scheme 19 Release of Methyl Acrylate from the W complex
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

24 Scheme 20 Fe-Mediated Transformations Leading to Multiple Products
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

25 Scheme 21 Pd-Catalyzed Methylsuccinic Anhydride and Glutaric Anhydride Synthesis by Osakada and Yamamoto Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

26 Scheme 22 Proposed Mechanism of Dibenedetto and Pápai's Ethyl Acrylate Synthesis Catalyzed by the (dppe)Pd–H Complex Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

27 Scheme 23 Limbach's Pd(dcpe)-Phenoxide Catalytic System
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

28 Scheme 24 Coupling of Dienes with CO2 Catalyzed by the Pd(dcpe) Complex Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions

29 Scheme 25 Aresta's Rhodialactone Formation Reaction
Chem 2017 3, DOI: ( /j.chempr ) Copyright © 2017 Elsevier Inc. Terms and Conditions


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