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Titolo:
COPPER CYANIDE-CATALYZED PALLADIUM COUPLING OF N-TERT-BUTOXYCARBONYL-PROTECTED ALPHA-LITHIO AMINES WITH ARYL IODIDES OR VINYL IODIDES
Autore:
DIETER RK; LI SJ;
Indirizzi:
CLEMSON UNIV,HOWARD L HUNTER CHEM LAB CLEMSON SC 29634
Titolo Testata:
Journal of organic chemistry
fascicolo: 22, volume: 62, anno: 1997,
pagine: 7726 - 7735
SICI:
0022-3263(1997)62:22<7726:CCPCON>2.0.ZU;2-S
Fonte:
ISI
Lingua:
ENG
Soggetto:
DIPOLE-STABILIZED CARBANIONS; CONJUGATE ADDITION-REACTIONS; BIDENTATE NITROGEN LIGANDS; CARBON BOND FORMATION; SYNTHETIC EQUIVALENTS; STEREOSELECTIVE SYNTHESIS; ORGANOCOPPER REAGENTS; ZEROVALENT PALLADIUM; OXIDATIVE ADDITION; GRIGNARD-REAGENTS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
82
Recensione:
Indirizzi per estratti:
Citazione:
R.K. Dieter e S.J. Li, "COPPER CYANIDE-CATALYZED PALLADIUM COUPLING OF N-TERT-BUTOXYCARBONYL-PROTECTED ALPHA-LITHIO AMINES WITH ARYL IODIDES OR VINYL IODIDES", Journal of organic chemistry, 62(22), 1997, pp. 7726-7735

Abstract

Treatment of (alpha-aminoalkyl)lithium reagents with aryl iodides in the presence of catalytic amounts of CuCN and PdCl2(PPh3)(2) or [(p-MeOC6H4)(3)P](4)Pd affords 2-aryl substituted amines in modest to good yields. The yields can be improved by use of softer ligands such as AsPh3 and SbPh3 or by use of bis(diphenylphosphino)ferrocene (dppf). Coupled products are obtained with electron-rich aryl iodides (XArI, X = Me, OMe), and the reaction fails with electron-poor aryl iodides (XArI,X = NO2, CO2Li). Treatment of the (alpha-aminoalkyl)lithium reagents with vinyl iodides and Pd(0)/dppf/CuCN afforded the coupling products in low to modest yields.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 30/03/20 alle ore 00:37:40