On the acidity and reactivity of highly effective chiral Brønsted acid catalysts: Establishment of an acidity scale

Karl Kaupmees; Nikita Tolstoluzhsky; Sadiya Raja; Magnus Rueping; Ivo Leito

doi:10.1002/anie.201303605

On the acidity and reactivity of highly effective chiral Brønsted acid catalysts: Establishment of an acidity scale

Karl Kaupmees, Nikita Tolstoluzhsky, Sadiya Raja, Magnus Rueping^*, Ivo Leito

^*Corresponding author for this work

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

150 Scopus citations

Abstract

Stronger acid, higher speed: The pK_a values of a range of binol-derived Brønsted acids of three different types were measured and found to correlate directly with the catalytic properties of the acids: higher rate constants k_I were observed for more acidic Brønsted acid catalysts (see plot; binol=1,1′-bi-2-naphthol).

Original language	English (US)
Pages (from-to)	11569-11572
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	44
DOIs	https://doi.org/10.1002/anie.201303605
State	Published - Oct 25 2013
Externally published	Yes

Keywords

N-triflylphosphoramides
Nazarov cyclization
acidity
organocatalysis
phosphoric acids

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201303605

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abstract = "Stronger acid, higher speed: The pKa values of a range of binol-derived Br{\o}nsted acids of three different types were measured and found to correlate directly with the catalytic properties of the acids: higher rate constants kI were observed for more acidic Br{\o}nsted acid catalysts (see plot; binol=1,1′-bi-2-naphthol).",

keywords = "N-triflylphosphoramides, Nazarov cyclization, acidity, organocatalysis, phosphoric acids",

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AU - Raja, Sadiya

AU - Rueping, Magnus

AU - Leito, Ivo

PY - 2013/10/25

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KW - N-triflylphosphoramides

KW - Nazarov cyclization

KW - acidity

KW - organocatalysis

KW - phosphoric acids

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IS - 44

ER -

On the acidity and reactivity of highly effective chiral Brønsted acid catalysts: Establishment of an acidity scale

Abstract

Keywords

ASJC Scopus subject areas

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