Palladium(0)-catalyzed cis-trans alkene isomerizations

被引：49

作者：

Canovese, Luciano ^{[1
]}

Santo, Claudio ^{[1
]}

Visentin, Fabiano ^{[1
]}

机构：

[1] Univ Ca Foscari, Dipartimento Chim, I-30123 Venice, Italy

来源：

ORGANOMETALLICS | 2008年 / 27卷 / 14期

关键词：

D O I：

10.1021/om800305h

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The cis-trans isomerization of some olefins bearing strong electron-withdrawing substituents (dmma and E-tse) is catalyzed by their mere coordination, to a suitable Pd(0) fragment without any external reagents. The choice of spectator ligand is fundamental to the efficiency of the process, and the phosphanyl-quinolines dppq and dppq-Me have proven to be particularly effective. The mechanism of the rearrangement is discussed, and the presence of electron-withdrawing and conjugated substituents on the olefins appears to be an essential prerequisite for the isomerization.

引用

页码：3577 / 3581

页数：5

共 39 条

[1]

BARTON D, 1979, COMPREHENSIVE ORGANI, V3, P1201

[2] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[3]

Benali O, 2002, EUR J ORG CHEM, V2002, P2317, DOI 10.1002/1099-0690(200207)2002:14<2317::AID-EJOC2317>3.0.CO

[4]

2-U

[5] STEREOCHEMICAL STUDY OF METATHESIS AND CIS-TRANS ISOMERIZATION OF 2-PENTENES [J].

BILHOU, JL ;

BASSET, JM ;

MUTIN, R ;

GRAYDON, WF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (12) :4083-4090

[6] MAGNESIUM IN METHANOL - SUBSTITUTE FOR SODIUM AMALGAM IN DESULFONYLATION REACTIONS [J].

BROWN, AC ;

CARPINO, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (10) :1749-1750

[7] INTERMEDIATES IN THE ASYMMETRIC HYDROGENATION OF UNSATURATED CARBOXYLIC-ACID DERIVATIVES [J].

BROWN, JM ;

PARKER, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (08) :342-344

[8] Insertion of substituted Alkynes into the Pd-C bond of methyl and vinyl palladium(II) complexes bearing pyridylthioethers as ancillary ligands. The influence of ligand substituents at pyridine and sulfur on the rate of insertion [J].

Canovese, L ;

Visentin, F ;

Chessa, G ;

Uguagliati, P ;

Santo, C ;

Dolmella, A .

ORGANOMETALLICS, 2005, 24 (13) :3297-3308

[9] Equilibria and rates of olefin substitution in zerovalent palladium complexes containing a 2-pyridylmethanimine ligand [J].

Canovese, L ;

Visentin, F ;

Uguagliati, P ;

Crociani, B .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1996, (09) :1921-1926

[10] The formation of a metallacycloheptadienyl intermediate in the reaction of palladacyclopentadienyl derivatives with tetracyanoethylene [J].

Canovese, Luciano ;

Visentin, Fabiano ;

Santo, Claudio .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (19) :4187-4192

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