1996
DOI: 10.1021/om9604031
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LiAl(OC(Ph)(CF3)2)4:  A Hydrocarbon-Soluble Catalyst for Carbon−Carbon Bond-Forming Reactions

Abstract: The compound LiAl(OC(Ph) (CF 3 ) 2 ) 4 (1), prepared from LiAlH 4 and HOC(Ph)(CF 3 ) 2 , is an active Lewis acid catalyst in toluene solution for the 1,4conjugate addition of silyl ketene acetals to R,β-unsaturated carbonyl compounds and for the direct substitution of allylic acetates by silyl ketene acetals. The structure of 1 contains a rare trigonal prismatic coordination sphere around the Li + cation, with two Li-O(C, Al) bonds and four Li-F(C) bonds.One of the most important uses of new weakly coordinati… Show more

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Cited by 103 publications
(54 citation statements)
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“…[12] The lithium salt of the Al{OCPh(CF 3 ) 2 } 4 À ion is an active Lewis acid catalyst in toluene for the 1,4-conjugate addition of silyl ketene acetals to a,b-unsaturated carbonyls and for the direct substitution of allylic acetates by silyl ketene acetals. [10] In addition, a solution of LiAl{OC(CF 3 ) 3 } 4 in 1,2-dimethoxyethane (DME; 0.01m) has a direct current (dc) conductivity that is nearly 100 times higher than a solution of LiCF 3 SO 3 in DME (0.01m). [13] We are investigating the relative Lewis basicities of Al(OR F ) 4 À superweak ions and the relative Lewis acidities of LiAl(OR F ) 4 compounds.…”
Section: Introductionmentioning
confidence: 99%
“…[12] The lithium salt of the Al{OCPh(CF 3 ) 2 } 4 À ion is an active Lewis acid catalyst in toluene for the 1,4-conjugate addition of silyl ketene acetals to a,b-unsaturated carbonyls and for the direct substitution of allylic acetates by silyl ketene acetals. [10] In addition, a solution of LiAl{OC(CF 3 ) 3 } 4 in 1,2-dimethoxyethane (DME; 0.01m) has a direct current (dc) conductivity that is nearly 100 times higher than a solution of LiCF 3 SO 3 in DME (0.01m). [13] We are investigating the relative Lewis basicities of Al(OR F ) 4 À superweak ions and the relative Lewis acidities of LiAl(OR F ) 4 compounds.…”
Section: Introductionmentioning
confidence: 99%
“…[5,7] Daher konnten WCA-Salze solch ungewöhnlicher Gasphasenkomplexe wie [Au(Xe) 4 ] 2+ , [8,9] oder [M(CO) n ] + (n = 1-4, M = Cu, [10] Ag [11][12][13] ) hergestellt werden. In dieser Weise ermöglichen auch [Al(OR F ) 4 ] À -WCAs (OR F = Fluoralkoxid) [14][15][16][17] die Stabilisierung und vollständige Charakterisierung von Salzen einiger Gasphasenkationen, die zuvor nur durch MS-Experimente bekannt waren. [7,[18][19][20][21] [22] unbekannten Stammverbindungen aller homolep-…”
unclassified
“…We attribute the unprecedented solubility to the aliphatic and therefore truly lipophilic molecular surface of the altebate anion. [7] The hydrogen atoms at the top layer of the molecular surface are positively polarized (Figure 2, top). In contrast to more fluorophilic WCAs such as the "Teflon ball" of the Krossing group (Figure 2, bottom), [8] the altebate can be considered as an anionic "wax ball".…”
Section: Resultsmentioning
confidence: 99%