Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

V. Fasano; J. H.W. LaFortune; J. M. Bayne; M. J. Ingleson; D. W. Stephan

doi:10.1039/c7cc09128a

Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

V. Fasano, J. H.W. LaFortune, J. M. Bayne, M. J. Ingleson^*, D. W. Stephan

^*Corresponding author for this work

University of Toronto

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

Abstract

A new class of electrophilic phosphonium cations (EPCs) containing a -CF₃ group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Brønsted acid, even at raised temperatures. Thus, P-CF₃ EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.

Original language	English
Pages (from-to)	662-665
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	6
Early online date	21 Dec 2017
DOIs	https://doi.org/10.1039/c7cc09128a
Publication status	Published - 2018

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10.1039/c7cc09128a

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title = "Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations",

abstract = "A new class of electrophilic phosphonium cations (EPCs) containing a -CF3 group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Br{\o}nsted acid, even at raised temperatures. Thus, P-CF3 EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.",

author = "V. Fasano and LaFortune, {J. H.W.} and Bayne, {J. M.} and Ingleson, {M. J.} and Stephan, {D. W.}",

year = "2018",

doi = "10.1039/c7cc09128a",

language = "English",

volume = "54",

pages = "662--665",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

number = "6",

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T1 - Air- and water-stable Lewis acids

T2 - Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

AU - Fasano, V.

AU - LaFortune, J. H.W.

AU - Bayne, J. M.

AU - Ingleson, M. J.

AU - Stephan, D. W.

PY - 2018

Y1 - 2018

N2 - A new class of electrophilic phosphonium cations (EPCs) containing a -CF3 group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Brønsted acid, even at raised temperatures. Thus, P-CF3 EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.

AB - A new class of electrophilic phosphonium cations (EPCs) containing a -CF3 group attached to the phosphorus(v) center is readily accessible in high yields, via a scalable process. These species are stable to air, water, alcohol and strong Brønsted acid, even at raised temperatures. Thus, P-CF3 EPCs are more robust than previously reported EPCs containing P-X moieties (X = F, Cl, OR), and despite their reduced Lewis acidity they function as Lewis acid catalysts without requiring anhydrous reaction conditions.

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U2 - 10.1039/c7cc09128a

DO - 10.1039/c7cc09128a

M3 - Article

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VL - 54

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EP - 665

JO - Chemical Communications

JF - Chemical Communications

IS - 6

ER -

Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

Abstract

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CCDC 1586281: Experimental Crystal Structure Determination

CCDC 1586279: Experimental Crystal Structure Determination

CCDC 1586280: Experimental Crystal Structure Determination

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Air- and water-stable Lewis acids: Synthesis and reactivity of P-trifluoromethyl electrophilic phosphonium cations

Abstract

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Datasets

CCDC 1586281: Experimental Crystal Structure Determination

CCDC 1586279: Experimental Crystal Structure Determination

CCDC 1586280: Experimental Crystal Structure Determination

Cite this