| Autor: |
Mansour, Tarek S., Bardhan, Sujata, Wan, Zhao-Kui |
| Předmět: |
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| Zdroj: |
Synlett; 2010, Issue 8, p1143-1169, 27p |
| Abstrakt: |
Phosphonium and benzotriazolyloxy (and related) intermediates are easily prepared by the reactions of cyclic amides and ureas with (1H-benzotriazol-1-yloxy)triaminophosphonium hexafluorophosphate related reagents. The former intermediates could also be made available using analogous phosphonium reagents prepared in situ or from commercial sources. These intermediates efficiently lead to carbon-nitrogen, carbon-oxygen, carbon-sulfur, and carbon-carbon bond formations through nucleophilic aromatic substitution reactions with various nucleophiles. A new �reaction involving the generation of phenols in situ from arylboronic acids and oxygen under palladium(0) catalysis or with boronic acids and hydrogen peroxide is reviewed. 1 Introduction 2 Phosphonium-Mediated Nucleophilic Aromatic Substitution Reactions of Heterocyclic Systems 2.1 Phosphonium-Mediated Carbon-Nitrogen Bond Forming Reactions via Modified Appel Conditions 2.2 Phosphonium-Mediated Carbon-Nitrogen Bond Forming Reactions via Commercially Available Phosphonium Reagents 2.2.1(1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate as an Activating Agent 2.2.2(1H-Benzotriazol-1-yloxy)tripyrrolidinylphosphonium Hexafluorophosphate and Bromotripyrrolidinylphosphonium Hexafluorophosphate as Activating Agents 2.2.3 Solvent and Base Effects 2.3 Reactivity of Various Phosphonium Reagents 2.4 Phosphonium-Mediated Carbon-Oxygen, Carbon-Sulfur, and Carbon-Carbon Bond Forming Reactions 3 Benzotriazolyloxy-Mediated and Related Bond-Forming Reactions of Heterocyclic Systems 4 Phosphonium-Mediated Reaction Mechanisms 4.1 Stepwise Pathways via Phosphonium and 1H-Benzotriazol-1-ol (or Pyridotriazol-1-ol) Adducts 4.2 1H-Benzotriazol-1-ol (or Pyridotriazol-1-ol) Adduct Independent Pathway 5 Palladium-Catalyzed Heteroaryl Ether Formation from Benzotriazolyloxy- or Pyridotriazolyloxy-Substituted Heterocycles with Arylboronic Acids 6 Unusual 1H-Benzotriazol-1-ol Adduct Rearrangement 7 A Tentative Protection and Amination Strategy Involving a 1H-Benzotriazol-1-ol Adduct 8 Conclusion and Outlook [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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