Heck coupling with nonactivated alkenyl tosylates and phosphates: Examples of effective 1,2-migrations of the alkenyl palladium(II) intermediates

被引：166

作者：

Hansen, Anders L.

Ebran, Jean-Philippe

Ahlquist, Marten

Norrby, Per-Ola

Skrydstrup, Troels

机构：

[1] Kemitorvet Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

[2] Univ Aarhus, inSPIN, Ctr Insoluble Prot Struct, Dept Chem, DK-8000 Aarhus, Denmark

[3] Univ Aarhus, Nanosci Ctr, DK-8000 Aarhus, Denmark

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 20期

关键词：

1,2-migration; alkenes; Heck reaction; phosphates; tosylates;

D O I：

10.1002/anie.200600442

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) What the Heck! A catalytic system composed of a Pd complex with a basic, hindered alkyl phosphine ligand is capable of promoting Heck coupling of nonactivated vinyl tosylates and phosphates with electron-deficient olefins. An unexpected 1,2-migration of the alkenyl Pd II intermediates (see Scheme) leads to the isomerized Heck coupling product. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3349 / 3353

页数：5

共 6 条

[1] Studies on the heck reaction with alkenyl phosphates: Can the 1,2-migration be controlled? Scope and limitations
Ebran, Jean-Philippe
Hansen, Anders L.
Gogsig, Thomas M.
Skrydstrup, Troels
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) : 6931 - 6942
[2] Convenient synthesis of alkenyl-, alkynyl-, and allenyl-substituted imidazo[1,2-a]pyridines via palladium-catalyzed cross-coupling reactions
Enguehard-Gueiffier, Cecile
Croix, Cecile
Hervet, Maud
Kazock, Jean-Yves
Gueiffier, Alain
Abarbri, Mohammed
HELVETICA CHIMICA ACTA, 2007, 90 (12) : 2349 - 2367
[3] A CONVENIENT SYNTHESIS OF 4-ALKENYL-2-CYCLOPENTEN-1-ONES BY PALLADIUM(II)-CATALYZED CROSS-COUPLING OF 4-BROMO-2-CYCLOPENTEN-1-ONE WITH 1-VINYLSTANNANES
TOLSTIKOV, GA
MIFTAKHOV, MS
DANILOVA, NA
VELDER, YL
SPIRIKHIN, LV
SYNTHESIS-STUTTGART, 1989, (08): : 625 - 627
[4] A synthesis of (E)-(1-organo-1-alkenyl)boronates by the palladium-catalyzed cross-coupling reaction of (E)-1,2-bis(boryl)-1-alkenes with organic halides: A formal carboboration of alkynes via the diboration-coupling sequence
Ishiyama, T
Yamamoto, M
Miyaura, N
CHEMISTRY LETTERS, 1996, (12) : 1117 - 1118
[5] NEW CATALYST PRECURSORS CONSTITUTED OF ASPH3 AND PALLADIUM ON CARBON OR PALLADIUM(II) ACETATE AS EFFICIENT PROMOTERS OF SELECTIVE CROSS-COUPLING REACTIONS BETWEEN FUNCTIONALIZED ALKENYL HALIDES AND ARYLZINC OR 1-ALKYNYLZINC CHLORIDES
ROSSI, R
BELLINA, F
CARPITA, A
GORI, R
SYNLETT, 1995, (04) : 344 - 346
[6] η5-Cyclopentadienyl-η3-1-phenylallylpalladium, an Unusually Effective Catalyst Precursor for Copper-Free and Copper-Assisted Sonogashira Cross-Coupling Reactions Catalyzed by Bis-phosphine Palladium(0) Compounds: The Role of Bis-acetylide Intermediates in the Reduction of a Palladium(II) Catalyst Precursor to a Palladium(0) Catalyst
Jaksic, Bryan E.
Jiang, Jingsi
Fraser, Andrew W.
Baird, Michael C.
ORGANOMETALLICS, 2013, 32 (15) : 4192 - 4198

← 1 →