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Titolo:
Dramatic enhancement of reactivity of organosilicon compounds induced by complexation of bis(allyl)silanes with fluoride ion
Autore:
Shibato, A; Itagaki, Y; Tayama, E; Hokke, Y; Asao, N; Maruoka, K;
Indirizzi:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ Kyoto Japan 6068502 Sch Sci, Dept Chem, Kyoto 6068502, Japan Hokkaido Univ, Grad Sch Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan Hokkaido Univ Sapporo Hokkaido Japan 0600810 oro, Hokkaido 0600810, Japan
Titolo Testata:
TETRAHEDRON
fascicolo: 30, volume: 56, anno: 2000,
pagine: 5373 - 5382
SICI:
0040-4020(20000721)56:30<5373:DEOROO>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
ORGANO-SILICON COMPOUNDS; HIGHLY STEREOSELECTIVE ALLYLATION; CATALYZED ALDOL REACTION; ENOL SILYL ETHERS; CARBONYL-COMPOUNDS; ALDEHYDES; CHEMISTRY; SILYLACETYLENES; ALKYLATION; KETONES;
Keywords:
fluoride ion; organosilicon compounds; bis(allyl)silanes;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
39
Recensione:
Indirizzi per estratti:
Indirizzo: Maruoka, K Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan KyotoUniv Kyoto Japan 6068502 ept Chem, Kyoto 6068502, Japan
Citazione:
A. Shibato et al., "Dramatic enhancement of reactivity of organosilicon compounds induced by complexation of bis(allyl)silanes with fluoride ion", TETRAHEDRON, 56(30), 2000, pp. 5373-5382

Abstract

New type of fluoride ion catalyzed allylation agent (1a, 1b), allenylationagent (9, 10), and alkynylation agent (17) can be successfully utilized for various carbonyl substrates. The rate acceleration is ascribable to the shift of equilibrium to the chelate complexes with Bu4NF by the favorable chelation of bis(silyl) compounds toward the fluoride ion. The F-19 NMR spectrum (ethyl trifluoroacetate as external standard) of a mixture of 1a and Bu4NF in CDCl3 showed two peaks at delta -81.75 and -77.67 (integration ratiosimilar to 9:1). The large signal corresponds to the original peak of Bu4NF and the small one might be ascribed to the chelate complex [B] between laand Bu4NF. The fluoride ion mediated reaction of bis(crotyldimethylsilyl)methane (7) with benzaldehyde was examined and the only gamma-adduct 8 was obtained regioselectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

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Documento generato il 23/09/20 alle ore 13:08:34