Palladium-catalyzed amination of aryl triflates

被引：205

作者：

Wolfe, JP ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 05期

关键词：

D O I：

10.1021/jo961915s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of aryl triflates to the corresponding aniline derivatives was accomplished in moderate to good yield using a catalyst consisting of the combination of palladium acetate (2 mol %) and either BINAP or Tol-BINAP. In contrast to the corresponding palladium-catalyzed amination of aryl bromides and iodides, electronically neutral aryl triflates gave higher yields of arylamines than did electron deficient aryl triflates, presumably due to the increased rate of base-promoted triflate cleavage in electron deficient substrates.

引用

收藏

页码：1264 / 1267

页数：4

相关论文

共 28 条

[1] RATES AND MECHANISMS OF OXIDATIVE ADDITION TO ZEROVALENT PALLADIUM COMPLEXES GENERATED IN-SITU FROM MIXTURES OF PD0(DBA)2 AND TRIPHENYLPHOSPHINE [J].

AMATORE, C ;

JUTAND, A ;

KHALIL, F ;

MBARKI, MA ;

MOTTIER, L .

ORGANOMETALLICS, 1993, 12 (08) :3168-3178

[2] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS [J].

CABRI, W ;

CANDIANI, I ;

BEDESCHI, A ;

PENCO, S ;

SANTI, R .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) :1481-1486

[3] PALLADIUM-CATALYZED CARBONYLATION OF ARYL TRIFLATES - SYNTHESIS OF ARENECARBOXYLIC ACID-DERIVATIVES FROM PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (33) :3931-3934

[4] PALLADIUM-CATALYZED TRIETHYLAMMONIUM FORMATE REDUCTION OF ARYL TRIFLATES - A SELECTIVE METHOD FOR THE DEOXYGENATION OF PHENOLS [J].

CACCHI, S ;

CIATTINI, PG ;

MORERA, E ;

ORTAR, G .

TETRAHEDRON LETTERS, 1986, 27 (45) :5541-5544

[5]

CADOGAN JIG, 1996, DICT ORGANIC COMPOUN, P5279

[6] 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

[7] PALLADIUM-CATALYZED COUPLING OF ARYL TRIFLATES WITH ORGANOSTANNANES [J].

ECHAVARREN, AM ;

STILLE, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5478-5486

[8] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY [J].

FARINA, V ;

KRISHNAN, B ;

MARSHALL, DR ;

ROTH, GP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5434-5444

[9]

GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481

[10] RATE AND MECHANISM OF OXIDATIVE ADDITION OF ARYL TRIFLATES TO ZEROVALENT PALLADIUM COMPLEXES - EVIDENCE FOR THE FORMATION OF CATIONIC (SIGMA-ARYL)PALLADIUM COMPLEXES [J].

JUTAND, A ;

MOSLEH, A .

ORGANOMETALLICS, 1995, 14 (04) :1810-1817