Tuning Reactivity and Chemoselectivity in Electron Transfer Initiated Cyclization Reactions: Applications to Carbon−Carbon Bond Formation
- 6 February 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (9), 2406-2407
- https://doi.org/10.1021/ja029139v
Abstract
In this communication, we demonstrate that the scope of our electron transfer initiated cyclization reaction can be significantly broadened by exploiting the relationship between the oxidation potentials of homobenzylic ethers and the mesolytic benzylic carbon−carbon bond dissociation energies of their radical cations. By lowering the oxidation potential of the electrophore and the benzylic carbon−carbon bond dissociation energy, we can initiate reactions under mild, nonphotochemical conditions. The selectivity of the arene oxidation and the mild reaction conditions allow a variety of electron-rich olefins to serve as nucleophilic groups to form carbon−carbon bonds with excellent efficiency.Keywords
This publication has 15 references indexed in Scilit:
- Electron Transfer Initiated Cyclizations: Cyclic Acetal Synthesis through Carbon−Carbon σ-Bond ActivationJournal of the American Chemical Society, 2001
- Two-Electron Sensitization: A New Concept for Silver Halide PhotographyJournal of the American Chemical Society, 2000
- A Kinetic Evaluation of Carbon−Hydrogen, Carbon−Carbon, and Carbon−Silicon Bond Activation in Benzylic Radical CationsJournal of the American Chemical Society, 1998
- Understanding Reactivity Patterns of Radical CationsAngewandte Chemie-International Edition, 1997
- Nucleophile-Assisted Cleavage of Benzyltrialkylsilane Cation RadicalsJournal of the American Chemical Society, 1997
- Domino Reactions in Organic SynthesisChemical Reviews, 1996
- Atom Economy—A Challenge for Organic Synthesis: Homogeneous Catalysis Leads the WayAngewandte Chemie-International Edition, 1995
- Intramolecular carbon-carbon bond formation by the anodic oxidation of unsaturated .alpha.-stannyl heteroatom compounds. Synthesis of fluorine containing heterocyclic compoundsJournal of the American Chemical Society, 1992
- Application of lanthanide reagents in organic synthesisChemical Reviews, 1992
- Hydrocarbon Bond Dissociation EnergiesAnnual Review of Physical Chemistry, 1982