Asymmetric Arylation of 2,2,2-Trifluoroacetophenones Catalyzed by Chiral Electrostatically-Enhanced Phosphoric Acids

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Abstract

A series of highly reactive metal-free chiral phosphoric acids possessing positively charged phosphonium ion substituents are reported and have been applied to Friedel-Crafts alkylations of indoles and 2,2,2-trifluoromethyl aryl ketones. These catalysts are orders-of-magnitude more active and have similar or better enantioselectivities than their noncharged analogues. High tolerance to a range of substrates with electron-withdrawing and electron-donating substituents was also observed.

Original languageEnglish (US)
Pages (from-to)2689-2692
Number of pages4
JournalOrganic Letters
Volume20
Issue number9
DOIs
StatePublished - May 4 2018

Bibliographical note

Funding Information:
Generous support from the National Science Foundation (CHE-1665392) and the Petroleum Research Fund (55631-ND4) as administered by the American Chemical Society is gratefully acknowledged.

Publisher Copyright:
© 2018 American Chemical Society.

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