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

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

The highly electrophilic fluorophosphonium cation [(C6F5)3PF]+[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...

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Veröffentlicht in:Organometallics 2018-10, Vol.37 (19), p.3303-3313
Hauptverfasser: Vogler, Maria, Süsse, Lars, LaFortune, James H. W, Stephan, Douglas W, Oestreich, Martin
Format: Artikel
Sprache:eng
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Zusammenfassung:The highly electrophilic fluorophosphonium cation [(C6F5)3PF]+[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.
ISSN:0276-7333
1520-6041
DOI:10.1021/acs.organomet.8b00496