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Titolo:
Highly active and selective catalysts for the formation of alpha-aryl ketones
Autore:
Fox, JM; Huang, XH; Chieffi, A; Buchwald, SL;
Indirizzi:
MIT, Dept Chem, Cambridge, MA 02139 USA MIT Cambridge MA USA 02139MIT, Dept Chem, Cambridge, MA 02139 USA
Titolo Testata:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
fascicolo: 7, volume: 122, anno: 2000,
pagine: 1360 - 1370
SICI:
0002-7863(20000223)122:7<1360:HAASCF>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
HETEROAROMATIC NUCLEOPHILIC-SUBSTITUTION; COUPLING REACTIONS; PHOTOSTIMULATED REACTIONS; REGIOSELECTIVE ARYLATION; REDUCTIVE ELIMINATION; PALLADIUM CATALYSIS; FORMING REACTION; SRN1 MECHANISM; COMPLEXES; HALIDES;
Tipo documento:
Review
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
68
Recensione:
Indirizzi per estratti:
Indirizzo: Buchwald, SL MIT, Dept Chem, 77 Massachusetts Ave, Cambridge, MA 02139 USAMIT 77 Massachusetts Ave Cambridge MA USA 02139 MA 02139 USA
Citazione:
J.M. Fox et al., "Highly active and selective catalysts for the formation of alpha-aryl ketones", J AM CHEM S, 122(7), 2000, pp. 1360-1370

Abstract

Bulky, electron-rich phosphine ligands with a biphenyl backbone, when combined with Pd(OAc)(2), give highly active catalysts for the alpha-arylation of ketones. The ligand 2-methyl-2'-dicyclohexylphosphinobiphenyl is particularly effective, and with 0.1-1.0 mol % Pd, a large variety of aryl halidesand ketones react efficiently and with high selectivity. For two types of substrates, the ligands BINAP and Xantphos are more effective than the biphenyl-based ligands. It is also shown that K3PO4 can be used as the base in these reactions, and that base-sensitive functional groups are better tolerated if this is used instead of NaO'Bu or NnHMDS. In some cases, alpha-arylketones can be produced without adding a ligand to the reaction. Although the substrate scope of the ligandless conditions is limited, some combinations react in high yield, and in one case, 100 000 turnovers were obtained. The results of experiments on the Pd-catalyzed arylation of diethyl malonate, cyclic 1,3-diketones, and nitroalkanes are also reported.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/12/20 alle ore 21:24:02