The nickel and palladium catalysed stereoselective cross coupling of cyclopropyl nucleophiles with aryl halides

被引：22

作者：

de Lang, RJ ^{[1
]}

Brandsma, L ^{[1
]}

机构：

[1] Univ Utrecht, Dept Preparat Organ Chem, NL-3584 CH Utrecht, Netherlands

来源：

SYNTHETIC COMMUNICATIONS | 1998年 / 28卷 / 02期

关键词：

D O I：

10.1080/00397919808005715

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with goad yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)(4). Other Ni- and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.

引用

页码：225 / 232

页数：8

共 14 条

[1] FACILE PALLADIUM-CATALYZED CROSS-COUPLING OF MONOORGANOZINC HALIDES WITH 3-IODOANTHRANILONITRILES [J].

CAMPBELL, JB ;

FIROR, JW ;

DAVENPORT, TW .

SYNTHETIC COMMUNICATIONS, 1989, 19 (13-14) :2265-2272

[2] SOLVOLYSIS OF CYCLOPROPYL HALIDES .2. 2-PHENYLCYCLOPROPYL BROMIDES [J].

HAUSSER, JW ;

GRUBBER, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (17) :2648-+

[3] DICHLORO[1,1'-BIS(DIPHENYLPHOSPHINO)FERROCENE]PALLADIUM-(II) - AN EFFECTIVE CATALYST FOR CROSS-COUPLING OF SECONDARY AND PRIMARY ALKYL GRIGNARD AND ALKYLZINC REAGENTS WITH ORGANIC HALIDES [J].

HAYASHI, T ;

KONISHI, M ;

KOBORI, Y ;

KUMADA, M ;

HIGUCHI, T ;

HIROTSU, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :158-163

[4]

HAYASHI T, 1979, TETRAHEDRON LETT, V21, P1871

[5] SYNTHESIS OF VINYLCYCLOPROPANES VIA PALLADIUM-CATALYZED COUPLING OF CYCLOPROPYLZINC HALIDES WITH VINYL IODIDES - TOTAL SYNTHESES OF (+/-)-PREZIZANOL AND (+/-)-PREZIZAENE [J].

PIERS, E ;

JEAN, M ;

MARRS, PS .

TETRAHEDRON LETTERS, 1987, 28 (43) :5075-5078

[6]

POWELL P, 1988, PRINCIPLES ORGANOMET, P51

[7] REACTIONS OF BIVALENT CARBON COMPOUNDS - REACTIVITIES IN OLEFIN-DIBROMOCARBENE REACTIONS [J].

SKELL, PS ;

GARNER, AY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (20) :5430-5433

[8] NEW CYCLOPROPYL BUILDING BLOCKS FOR ORGANIC SYNTHESIS .9. NUCLEOPHILIC SUBSTITUTIONS OF 1-ALKENYLCYCLOPROPYL ESTERS AND 1-ALKYNYLCYCLOPROPYL CHLORIDES CATALYZED BY PALLADIUM(O) [J].

STOLLE, A ;

OLLIVIER, J ;

PIRAS, PP ;

SALAUN, J ;

DEMEIJERE, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (11) :4051-4067

[9]

STOLLE A, 1991, SYNLETT, P327

[10] NICKEL-PHOSPHINE COMPLEX-CATALYZED GRIGNARD COUPLING .1. CROSS-COUPLING OF ALKYL, ARYL, AND ALKENYL GRIGNARD-REAGENTS WITH ARYL AND ALKENYL HALIDES - GENERAL SCOPE AND LIMITATIONS [J].

TAMAO, K ;

SUMITANI, K ;

KISO, Y ;

ZEMBAYASHI, M ;

FUJIOKA, A ;

KODAMA, S ;

NAKAJIMA, I ;

MINATO, A ;

KUMADA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (07) :1958-1969

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