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

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Presentation transcript:

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 581-591 (October 2016) DOI: 10.1016/j.chempr.2016.09.005 Copyright © 2016 Elsevier Inc. Terms and Conditions

Chem 2016 1, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

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, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

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, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

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, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

Scheme 2 Preliminary Discovery Chem 2016 1, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

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, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

Scheme 4 Marco Lactone Formation via Vicinal Regioselective Functionalization of Arene Chem 2016 1, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions

Scheme 5 The Scope of the Reaction HCTU, O-(6-chlorobenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate. Chem 2016 1, 581-591DOI: (10.1016/j.chempr.2016.09.005) Copyright © 2016 Elsevier Inc. Terms and Conditions