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

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/intramolecula...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2010-05, Vol.132 (18), p.6412-6418
Main Authors: Kinoshita, Hidenori, Ingham, Oscar J, Ong, Winnie W, Beeler, Aaron B, Porco, John A
Format: Article
Language:English
Subjects:
Acetic Anhydrides
Catalysis
Fluoroacetates
Imines - chemistry
Lanthanum - chemistry
Models, Molecular
Molecular Conformation
Phosphines - chemistry
Quantum Theory
Trifluoroacetic Acid - chemistry
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja100346w