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Jianchun Wang, Lei Zhang, Zhe Dong, Guangbin Dong  Chem 

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Presentation on theme: "Jianchun Wang, Lei Zhang, Zhe Dong, Guangbin Dong  Chem "— Presentation transcript:

1 Reagent-Enabled ortho-Alkoxycarbonylation of Aryl Iodides via Palladium/Norbornene Catalysis 
Jianchun Wang, Lei Zhang, Zhe Dong, Guangbin Dong  Chem  Volume 1, Issue 4, Pages (October 2016) DOI: /j.chempr Copyright © 2016 Elsevier Inc. Terms and Conditions

2 Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

3 Figure 1 Scope of Substrates of Unsymmetrical Carbonate Anhydrides
All yields are isolated yields. 8f was run with 1.0 equiv of 7f. Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

4 Figure 2 Scope of Substrates of Aryl Iodides and Olefins
All yields are isolated yields. 8l and 8m were run in tetrahydrofuran with 0.5 equiv of additional ethyl chloroformate. 8z was run with 2.5 equiv of 7a. Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

5 Scheme 1 Palladium/Norbornene Catalysis (A) Summary of prior art.6–11
(B) Our previous work. (C) Mixed anhydride reagents. (D) This work. (E) Selected examples of natural products.12–17 Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

6 Scheme 2 Preliminary Discovery
Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

7 Scheme 3 Selected Controlled Experiment and Optimization
All yields were determined by 1H-NMR using 1,3,5-trimethoxybenzene as the internal standard. Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

8 Scheme 4 Marco Lactone Formation via Vicinal Regioselective Functionalization of Arene Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions

9 Scheme 5 The Scope of the Reaction
HCTU, O-(6-chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate. Chem 2016 1, DOI: ( /j.chempr ) Copyright © 2016 Elsevier Inc. Terms and Conditions


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