Electrophilic activation of alkenes by platinum(II):: So much more than a slow version of palladium(II)

被引:246
作者
Chianese, Anthony R.
Lee, Stephen J.
Gagne, Michel R.
机构
[1] Colgate Univ, Dept Chem, Hamilton, NY 13346 USA
[2] USA, Res Off, Res Triangle Pk, NC 27709 USA
[3] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA
关键词
alkene ligands; cyclization; electrophilic addition; homogeneous catalysis; platinum;
D O I
10.1002/anie.200603954
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The electrophilic activation of alkenes by transition-metal catalysts is a fundamental step in a rapidly growing number of catalytic processes. Although palladium is the best known metal for this purpose, the special properties of its third-row cousin platinum (strong metal-ligand bonds and slow substitution kinetics) have enabled the development of transformations that are initiated by addition to the C=C bonds by protic carbon, nitrogen, oxygen, and phosphorus nucleophiles, as well as alkene or arene nucleophiles. Additionally, reactivity profiles, which are often unique to platinum, provide wholly new reaction products. This Review concerns platinum-catalyzed electrophilic alkene activation reactions, with a special emphasis on the mechanistic properties of known systems, on the differences between platinum and palladium catalysts, and on the prospects for the development of new systems. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4042 / 4059
页数:18
相关论文
共 133 条
[61]   Addition of arenes to ethylene and propene catalyzed by ruthenium [J].
Lail, M ;
Arrowood, BN ;
Gunnoe, TB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (25) :7506-7507
[62]   Mechanistic aspects of C-H activation by Pt complexes [J].
Lersch, M ;
Tilset, M .
CHEMICAL REVIEWS, 2005, 105 (06) :2471-2526
[63]   Bronsted acid catalyzed addition of phenols, carboxylic acids, and tosylamides to simple olefins [J].
Li, Zigang ;
Zhang, Junliang ;
Brouwer, Chad ;
Yang, Cai-Guang ;
Reich, Nicholas W. ;
He, Chuan .
ORGANIC LETTERS, 2006, 8 (19) :4175-4178
[64]   Scope and mechanism of the PdII-catalyzed arylation/carboalkoxylation of unactivated olefins with indoles [J].
Liu, C ;
Widenhoefer, RA .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (08) :2371-2382
[65]   Platinum(II)/europium(III)-catalyzed intramolecular hydroalkylation of 4-pentenyl β-dicarbonyl compounds [J].
Liu, C ;
Widenhoefer, RA .
TETRAHEDRON LETTERS, 2005, 46 (02) :285-287
[66]   Platinum-catalyzed intramolecular alkylation of indoles with unactivated olefins [J].
Liu, C ;
Han, XQ ;
Wang, X ;
Widenhoefer, RA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3700-3701
[67]   Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and SN2 C-O bond formation [J].
Liu, Guosheng ;
Stahl, Shannon S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (22) :7179-7181
[68]   EPOXIDATION OF OLEFINS BY WATER OXYGEN CATALYZED BY PLATINUM BLUE COMPLEXES [J].
MATSUMOTO, K ;
MIZUNO, K ;
ABE, T ;
KINOSHITA, J ;
SHIMURA, H .
CHEMISTRY LETTERS, 1994, (07) :1325-1328
[69]   A synthetic route to alkyl-PtIII dinuclear complexes from olefins and its implication on the olefin oxidation catalyzed by amidate-bridged PtIII dinuclear complexes [J].
Matsumoto, K ;
Nagai, Y ;
Matsunami, J ;
Mizuno, K ;
Abe, T ;
Somazawa, R ;
Kinoshita, J ;
Shimura, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (12) :2900-2907
[70]   Metal-initiated amination of alkenes and alkynes [J].
Muller, TE ;
Beller, M .
CHEMICAL REVIEWS, 1998, 98 (02) :675-703