Synthesis of Acrylic Acid Derivatives from CO2 and Ethylene

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Synthesis of Acrylic Acid Derivatives from CO2 and Ethylene Xiao Wang, Hui Wang, Yuhan Sun  Chem  Volume 3, Issue 2, Pages 211-228 (August 2017) DOI: 10.1016/j.chempr.2017.07.006 Copyright © 2017 Elsevier Inc. Terms and Conditions

Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Figure 1 Buntine's Calculated Free Energy of Intermediates in a Ni(mDBU)2-Facilitated Reaction Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Figure 2 Resulting Complexes in the Early Study of Mo- and W-Assisted CO2-Ethylene Coupling Reactions Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 1 Synthesis of Acrylate from CO2 and Ethylene Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 2 Hoberg's CO2-Norbornene Addition Reaction Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 3 Walther's CO2-Diene Addition Reaction Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 4 Hoberg's CO2-Ethylene Addition Reaction and the Formation of Nickelalactone Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 5 Synthesis of Cinnamic Acid from CO2 and Styrene Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 6 Formation of Walther's Binuclear Ni(I) Complex Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 7 Hypothetical Catalytic Cycle of Rieger's Methylation of Nickelalactone and Synthesis of Methyl Acrylate Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 8 Reaction Mechanism with the Ni-TMEDA Complex Proposed by Kühn Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 9 Proposed Reaction Pathways with the Ni-dtbpe Complex by Limbach and Hoffmann Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

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, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 11 Limbach's Catalytic System Consisting of Ni-dtbpe-tBuONa Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 12 Limbach's Reaction with (BenzP*)nickelalactone as Intermediate Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 13 Vogt's Reaction Facilitated by Lithium Salt Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 14 Stabilization Effect by Sodium Cation Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 15 Acceleration of β-hydride Elimination by an Electron-Deficient Borane Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 16 The Expected Catalytic Cycle of Bernskoetter's Mo catalysis Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 17 Formation of Carbonylation Products by Bernskoetter's Mo-tetrahydride Complex Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 18 Preparation of a W complex and the Formation-Isomerization of the Oxidative Addition Product Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 19 Release of Methyl Acrylate from the W complex Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 20 Fe-Mediated Transformations Leading to Multiple Products Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 21 Pd-Catalyzed Methylsuccinic Anhydride and Glutaric Anhydride Synthesis by Osakada and Yamamoto Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 22 Proposed Mechanism of Dibenedetto and Pápai's Ethyl Acrylate Synthesis Catalyzed by the (dppe)Pd–H Complex Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 23 Limbach's Pd(dcpe)-Phenoxide Catalytic System Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 24 Coupling of Dienes with CO2 Catalyzed by the Pd(dcpe) Complex Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions

Scheme 25 Aresta's Rhodialactone Formation Reaction Chem 2017 3, 211-228DOI: (10.1016/j.chempr.2017.07.006) Copyright © 2017 Elsevier Inc. Terms and Conditions