CF(3)‐Containing para‐Quinone Methides for Organic Synthesis

A new family of CF(3)‐containing para‐quinone methides (CF(3)‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF(3)‐containing stereogenic center straightforwardly. The electrophilicity...

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Detalles Bibliográficos
Autores principales: Winter, Michael, Schütz, Roman, Eitzinger, Andreas, Ofial, Armin R., Waser, Mario
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7335660/
https://www.ncbi.nlm.nih.gov/pubmed/32624681
http://dx.doi.org/10.1002/ejoc.202000295
Descripción
Sumario:A new family of CF(3)‐containing para‐quinone methides (CF(3)‐QMs) was systematically investigated for its suitability in organic synthesis. Addition of different nucleophiles gives access to target molecules with a benzylic CF(3)‐containing stereogenic center straightforwardly. The electrophilicity parameter E of the prototypical CF(3)‐QM 2,6‐di‐tert‐butyl‐4‐(2,2,2‐trifluoroethylidene)cyclohexa‐2,5‐dien‐1‐one was determined to be –11.68 according to the Mayr scale, making it one of the most reactive quinone methides known so far.

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