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2010•Journal of the American Chemical SocietyOpen access

Tandem Processes Identified from Reaction Screening: Nucleophilic Addition to Aryl N-Phosphinylimines Employing La(III)-TFAA Activation

Hidenori Kinoshita, O.J. Ingham, W.W. Ong, Aaron B. Beeler, John A. Porco

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Abstract

Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.

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Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.

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Available abstract

Reaction screening of nucleophilic reaction partners for addition to N-diphenylphosphinylimines employing lanthanum(III) triflate as a catalyst and trifluoroacetic anhydride (TFAA) as an activator is reported. A number of tandem processes leading to novel chemotypes including aza-Prins/intramolecular Friedel-Crafts annulations have been identified, and both reaction scope and mechanism further investigated.

Key concepts: Chemistry, Trifluoromethanesulfonate, Intramolecular force, Trifluoroacetic anhydride, Nucleophile, Aryl, Catalysis, Nucleophilic addition

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