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

Jie Ma; Steven R. Kass

doi:10.1021/acs.orglett.8b00900

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

Jie Ma, Steven R. Kass

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

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 language	English (US)
Pages (from-to)	2689-2692
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.8b00900
State	Published - 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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title = "Asymmetric Arylation of 2,2,2-Trifluoroacetophenones Catalyzed by Chiral Electrostatically-Enhanced Phosphoric Acids",

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.",

author = "Jie Ma and Kass, {Steven R.}",

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: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = may,

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doi = "10.1021/acs.orglett.8b00900",

language = "English (US)",

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T1 - Asymmetric Arylation of 2,2,2-Trifluoroacetophenones Catalyzed by Chiral Electrostatically-Enhanced Phosphoric Acids

AU - Ma, Jie

AU - Kass, Steven R.

N1 - 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.

PY - 2018/5/4

Y1 - 2018/5/4

N2 - 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.

AB - 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.

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ER -

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

Abstract

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