Palladium/tetraphosphine catalysed heck reaction with ortho-substituted aryl bromides

被引：48

作者：

Feuerstein, M ^{[1
]}

Doucet, H ^{[1
]}

Santelli, M ^{[1
]}

机构：

[1] Fac Sci & Tech St Jerome, Lab Synth Organ Associe, CNRS, F-13397 Marseille 20, France

来源：

SYNLETT | 2001年 / 12期

关键词：

catalysis; palladium; tetraphosphine; Heck reaction; aryl bromides;

D O I：

10.1055/s-2001-18752

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tetraphosphine cis,cis,cis-1,2,3,4- tetrakis(diphenlylphosphinomethyl)cyclopentane associated to [PdCl(C3H5)](2) catalyses the Heck reaction of butyl acrylate with a wide range of sterically demanding aryl bromides, furnishing the addition product in high yields. Turnover numbers as high as 30-89000 have been obtained using ortho-substituted aryl bromides and 43-2600 with di-ortho-substituted aryl bromides in the presence of this catalyst.

引用

页码：1980 / 1982

页数：3

共 37 条

[1] Orthopalladated triarylphosphite complexes as highly efficient catalysts in the Heck reaction
Albisson, DA
Bedford, RB
Scully, PN
[J]. TETRAHEDRON LETTERS, 1998, 39 (52) : 9793 - 9796
[2] THE FORMATION OF 3-METHYL-1A,7B-DIHYDRO-1H-CYCLOPROP[C]ISOQUINOLINE FROM TRANS-N-[2-(2-ACETYLPHENYL)CYCLOPROPYL]-2-(TRIMETHYLSILYL)ETHYLCARBAMATE
APPELBERG, U
VALLGARDA, J
HACKSELL, U
[J]. TETRAHEDRON LETTERS, 1994, 35 (20) : 3417 - 3420
[3] The heck reaction as a sharpening stone of palladium catalysis
Beletskaya, IP
Cheprakov, AV
[J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
[4] Beller M, 1998, SYNLETT, P792
[5] New highly active chiral phosphapalladacycle catalysts. First isolation and characterization of a Pd(IV) intermediate
Brunel, JM
Hirlemann, MH
Heumann, A
Buono, G
[J]. CHEMICAL COMMUNICATIONS, 2000, (19) : 1869 - 1870
[6] Brunel JM, 2000, ANGEW CHEM INT EDIT, V39, P1946, DOI 10.1002/1521-3773(20000602)39:11<1946::AID-ANIE1946>3.3.CO
[7] 2-9
[8] Heck reactions under microwave irradiation in solvent-free conditions
DiazOrtiz, A
Prieto, P
Vazquez, E
[J]. SYNLETT, 1997, (03) : 269 - &
[9] Efficient Heck vinylation of aryl halides catalyzed by a new air-stable palladium-tetraphosphine complex
Feuerstein, M
Doucet, H
Santelli, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (17) : 5923 - 5925
[10] Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids
Feuerstein, M
Doucet, H
Santelli, M
[J]. TETRAHEDRON LETTERS, 2001, 42 (38) : 6667 - 6670

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