4.5 Article

Electrophilic Phosphonium Cations as Lewis Acid Catalysts in Diels-Alder Reactions and Nazarov Cyclizations

Journal

ORGANOMETALLICS
Volume 37, Issue 19, Pages 3303-3313

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.organomet.8b00496

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Funding

  1. Einstein Visiting Fellowship of the Einstein Foundation Berlin
  2. Einstein Foundation Berlin
  3. NSERC of Canada
  4. Canada Research Chair

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The highly electrophilic fluorophosphonium cation [(C6F5)(3)PF](+)[B(C6F5)(4)](-) is shown to catalyze Diels-Alder reactions of challenging dienophile/enophile combinations and Nazarov cyclizations of various precursors. Several other electrophilic phosphonium cations (EPCs) have been tested for comparison. This systematic study demonstrates the power of these Lewis acids to act as catalysts for synthetically useful pericyclic reactions.

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