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

被引：746

作者：

Hartwig, JF ^{[1
]}

Kawatsura, M ^{[1
]}

Hauck, SI ^{[1
]}

Shaughnessy, KH ^{[1
]}

Alcazar-Roman, LM ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 15期

关键词：

D O I：

10.1021/jo990408i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of aryl bromides with amines occurs at room temperature when using Pd(0) and P(t-Bu)(3) in a 1:1 ratio, and the reactions of aryl chlorides occur at room temperature or 70 degrees C. The arylation of indoles and the new arylation of carbamates also occur when using P(t-Bu)(3) as ligand.

引用

收藏

页码：5575 / 5580

页数：6

相关论文

共 68 条

[1] CARBON-HETEROATOM BOND-FORMING REDUCTIVE ELIMINATION - MECHANISM, IMPORTANCE OF TRAPPING REAGENTS, AND UNUSUAL ELECTRONIC EFFECTS DURING FORMATION OF ARYL SULFIDES [J].

BARANANO, D ;

HARTWIG, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) :2937-2938

[2] Formal [4+3], [4+2], [4+1] and [2+1] cycloadditions and acid-base reaction of 2-methyl-1,3-dimorpholino-1,3-butadiene with Fischer carbene complexes [J].

Barluenga, J ;

Aznar, F ;

Fernandez, M .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) :1629-1637

[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] New triarylamine-containing polymers as hole transport materials in organic light-emitting diodes: Effect of polymer structure and cross-linking on device characteristics [J].

Bellmann, E ;

Shaheen, SE ;

Thayumanavan, S ;

Barlow, S ;

Grubbs, RH ;

Marder, SR ;

Kippelen, B ;

Peyghambarian, N .

CHEMISTRY OF MATERIALS, 1998, 10 (06) :1668-1676

[5] PALLADIUM-CATALYZED VINYLATION OF ARYL CHLORIDES - CHELATE EFFECT IN CATALYSIS [J].

BENDAVID, Y ;

PORTNOY, M ;

GOZIN, M ;

MILSTEIN, D .

ORGANOMETALLICS, 1992, 11 (06) :1995-1996

[6] CHELATE-ASSISTED, PD-CATALYZED EFFICIENT CARBONYLATION OF ARYL CHLORIDES [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (23) :8742-8744

[7] FORMYLATION OF ARYL CHLORIDES CATALYZED BY A PALLADIUM COMPLEX [J].

BENDAVID, Y ;

PORTNOY, M ;

MILSTEIN, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (23) :1816-1817

[8] New efficient nickey(0) catalysed amination of aryl chlorides [J].

Brenner, E ;

Fort, Y .

TETRAHEDRON LETTERS, 1998, 39 (30) :5359-5362

[9] Carbon-nitrogen-bond-forming reductive elimination of arylamines from palladium(II) phosphine complexes [J].

Driver, MS ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (35) :8232-8245

[10] A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].

Driver, MS ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218

← 1 2 3 4 5 6 7 →