Solvent free amination reactions of aryl bromides at room temperature catalyzed by a (π-allyl)palladium complex bearing a diphosphinidenecyclobutene ligand

被引：48

作者：

Gajare, AS

Toyota, K

Yoshifuji, M ^{[1
]}

Ozawa, F

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

[2] Kyoto Univ, Chem Res Inst, Uji, Kyoto 6110011, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 19期

关键词：

D O I：

10.1021/jo049087n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An air- and moisture-stable ( T-allyl)palladium complex bearing a unique diphosphinidenecyclobutene ligand effectively catalyzes amination reactions of aryl bromides with amines, where the reactions proceed under mild conditions without solvent, with 2 mol % of catalyst and I equiv of t-BuOK at room temperature. Under these conditions the amination. products were obtained in good to excellent isolated yields.

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页码：6504 / 6506

页数：3

相关论文

共 48 条

[1] Mechanism of aryl chloride amination: Base-induced oxidative addition [J].

Alcazar-Roman, LM ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12905-12906

[2] LOW COORDINATED PHOSPHORUS-COMPOUNDS .56. VALENCE ISOMERIZATION OF A 3,4-DIPHOSPHA-1,5-HEXADIYNE WITH FORMATION OF A 3,4-BIS(PHOSPHAMETHYLENE)-1-CYCLOBUTENE [J].

APPEL, R ;

WINKHAUS, V ;

KNOCH, F .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (02) :243-245

[3] First palladium-catalyzed aminations of aryl chlorides [J].

Beller, M ;

Riermeier, TH ;

Reisinger, CP ;

Herrmann, WA .

TETRAHEDRON LETTERS, 1997, 38 (12) :2073-2074

[4] A RARE, LOW-VALENT ALKYLAMIDO COMPLEX, A DIPHENYLAMIDO COMPLEX, AND THEIR REDUCTIVE ELIMINATION OF AMINES BY 3-COORDINATE INTERMEDIATES [J].

DRIVER, MS ;

HARTWIG, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (16) :4708-4709

[5]

Guari Y, 2001, CHEM-EUR J, V7, P475, DOI 10.1002/1521-3765(20010119)7:2<475::AID-CHEM475>3.0.CO

[6]

2-6

[7]

Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO

[8]

2-L

[9] OXIDATIVE ADDITION OF ARYL BROMIDE AFTER DISSOCIATION OF PHOSPHINE FROM A 2-COORDINATE PALLADIUM(0) COMPLEX, BIS(TRI-O-TOLYLPHOSPHINE)PALLADIUM(0) [J].

HARTWIG, JF ;

PAUL, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (19) :5373-5374

[10] Room-temperature palladium-catalyzed amination of aryl bromides and chlorides and extended scope of aromatic C-N bond formation with a commercial ligand [J].

Hartwig, JF ;

Kawatsura, M ;

Hauck, SI ;

Shaughnessy, KH ;

Alcazar-Roman, LM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5575-5580

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