C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling

被引：186

作者：

Bermejo, Antonio ^{[1
]}

Ros, Abel ^{[1
,2
]}

Fernandez, Rosario ^{[1
]}

Lassaletta, Jose M. ^{[2
]}

机构：

[1] Univ Seville, Dept Quim Organ, Seville 41071, Spain

[2] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 47期

关键词：

D O I：

10.1021/Ja8074693

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Glyoxal bis-hydrazone derived from (S,S)-1-amino-2,5-diphenytpyrrolidine behaves as an excellent ligand for phosphine-free, asymmetric Suzuki-Miyaura cross couplings, thereby affording a variety of enantiomerically enriched biaryls with different substitution patterns. The high catalytic activity of the [PdCl2(bis-hydrazone)] complex allows reactions to be performed at room temperature, affording products with excellent enantioselectivities in all cases.

引用

页码：15798 / +

页数：3

共 19 条

[1]

Baudoin O., 2003, Stud. Nat. Prod. Chem., V29, P355, DOI DOI 10.1016/S1572-5995(03)80011-X

[2] Aminophosphine-oxazoline and phosphoramidite-oxazoline ligands and their application in asymmetric catalysis [J].

Bronger, Raymond P. J. ;

Guiry, Patrick J. .

TETRAHEDRON-ASYMMETRY, 2007, 18 (09) :1094-1102

[3] The first asymmetric Suzuki cross-coupling reaction [J].

Cammidge, AN ;

Crépy, KVL .

CHEMICAL COMMUNICATIONS, 2000, (18) :1723-1724

[4] Asymmetric Suzuki cross-coupling reaction: chirality reversal depending on the palladium-chiral phosphine ratio [J].

Castanet, AS ;

Colobert, F ;

Broutin, PE ;

Obringer, M .

TETRAHEDRON-ASYMMETRY, 2002, 13 (06) :659-665

[5] Efficient synthesis of chiral 1,1′-binaphthalenes by the asymmetric Suzuki-Miyaura reaction:: Dramatic synthetic improvement by simple purification of naphthylboronic acids [J].

Genov, Miroslav ;

Almorin, Antonio ;

Espinet, Pablo .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (36) :9346-9352

[6] Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system [J].

Grasa, GA ;

Hillier, AC ;

Nolan, SP .

ORGANIC LETTERS, 2001, 3 (07) :1077-1080

[7] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .6. PRACTICAL ASYMMETRIC-SYNTHESIS OF 1,1'-BINAPHTHYLS VIA ASYMMETRIC CROSS-COUPLING WITH A CHIRAL [(ALKOXYALKYL)FERROCENYL]MONOPHOSPHINE NICKEL-CATALYST [J].

HAYASHI, T ;

HAYASHIZAKI, K ;

KIYOI, T ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) :8153-8156

[8] Asymmetric synthesis of an axially chiral antimitotic biaryl via an atropo-enantioselective Suzuki cross-coupling [J].

Herrbach, A ;

Marinetti, A ;

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4897-4905

[9] Density functional studies on palladium-catalyzed Suzuki-Miyaura cross-coupling reactions assisted by N- or P-chelating ligands [J].

Huang, Yi-Luen ;

Weng, Chia-Ming ;

Hong, Fung-E. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (14) :4426-4434

[10] New air-stable planar chiral ferrocenyl monophosphine ligands: Suzuki cross-coupling of aryl chlorides and bromides [J].

Jensen, JF ;

Johannsen, M .

ORGANIC LETTERS, 2003, 5 (17) :3025-3028

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