NICKEL-CATALYZED OR PALLADIUM-CATALYZED CROSS COUPLING .31. PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTIONS OF ALKENYLMETALS WITH UNSATURATED ORGANIC HALIDES AS A SELECTIVE ROUTE TO ARYLATED ALKENES AND CONJUGATED DIENES - SCOPE, LIMITATIONS, AND MECHANISM

被引:285
作者
NEGISHI, E [1 ]
TAKAHASHI, T [1 ]
BABA, S [1 ]
VANHORN, DE [1 ]
OKUKADO, N [1 ]
机构
[1] SYRACUSE UNIV,DEPT CHEM,SYRACUSE,NY 13210
关键词
D O I
10.1021/ja00242a024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:2393 / 2401
页数:9
相关论文
共 52 条
[21]   PALLADIUM-CATALYZED COUPLING OF TETRAORGANOTIN COMPOUNDS WITH ARYL AND BENZYL HALIDES - SYNTHETIC UTILITY AND MECHANISM [J].
MILSTEIN, D ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4992-4998
[22]   MECHANISM OF REDUCTIVE ELIMINATION - REACTION OF ALKYLPALLADIUM(II) COMPLEXES WITH TETRAORGANOTIN, ORGANOLITHIUM, AND GRIGNARD-REAGENTS - EVIDENCE FOR PALLADIUM(IV) INTERMEDIACY [J].
MILSTEIN, D ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4981-4991
[23]   A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-ALKADIENES AND (Z,Z)-ALKADIENES BY A PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL BROMIDES [J].
MIYAURA, N ;
SUGINOME, H ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1981, 22 (02) :127-130
[24]   NOVEL AND CONVENIENT METHOD FOR THE STEROSPECIFIC AND REGIOSPECIFIC SYNTHESIS OF CONJUGATED ALKADIENES AND ALKENYNES VIA THE PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH BROMOALKENES AND BROMOALKYNES [J].
MIYAURA, N ;
YAMADA, K ;
SUGINOME, H ;
SUZUKI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (04) :972-980
[25]   MECHANISMS OF 1,1-REDUCTIVE ELIMINATION FROM PALLADIUM - ELIMINATION OF ETHANE FROM DIMETHYLPALLADIUM(II) AND TRIMETHYLPALLADIUM(IV) [J].
MORAVSKIY, A ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (14) :4182-4186
[26]   MECHANISTIC STUDIES OF NICKEL CATALYSIS IN CROSS COUPLING OF ARYL HALIDES WITH ALKYLMETALS - ROLE OF ARYLALKYLNICKEL(II) SPECIES AS INTERMEDIATES [J].
MORRELL, DG ;
KOCHI, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (25) :7262-7270
[27]   STEREOSELECTIVE SYNTHESIS OF ALKENES AND ALKENYL SULFIDES FROM ALKENYL HALIDES USING PALLADIUM AND RUTHENIUM CATALYSTS [J].
MURAHASHI, SI ;
YAMAMURA, M ;
YANAGISAWA, K ;
MITA, N ;
KONDO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2408-2417
[28]   SELECTIVE CARBON-CARBON BOND FORMATION VIA TRANSITION-METAL CATALYSIS .4. NOVEL-APPROACH TO CROSS-COUPLING EXEMPLIFIED BY NICKEL-CATALYZED REACTION OF ALKENYLZIRCONIUM DERIVATIVES WITH ARYL HALIDES [J].
NEGISHI, E ;
VANHORN, DE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (09) :3168-3170
[29]   NOVEL STEREOSELECTIVE ALKENYL-ARYL COUPLING VIA NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ARYL HALIDES [J].
NEGISHI, E ;
BABA, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (15) :596-597
[30]   BIS(TRIPHENYLPHOSPHINE)PALLADIUM - ITS GENERATION, CHARACTERIZATION, AND REACTIONS [J].
NEGISHI, E ;
TAKAHASHI, T ;
AKIYOSHI, K .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (17) :1338-1339