Reactivity of "Frustrated Lewis pairs": Three-component reactions of phosphines, a borane, and olefins

被引：413

作者：

McCahill, Jenny S. J. ^{[1
]}

Welch, Gregory C. ^{[1
]}

Stephan, Douglas W. ^{[1
]}

机构：

[1] Univ Windsor, Dept Chem & Biochem, Windsor, ON N9B 3P4, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 26期

关键词：

addition; alkenes; Lewis acids; Lewis bases; phosphanes;

D O I：

10.1002/anie.200701215

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

All or nothing: Sterically frustrated Lewis pairs of phosphines and the borane B(C6F5)3 exhibit unprecedented reactivity with olefins to afford both inter- and intramolecular alkanediyl-linked phosphonium borates (see picture; black C, pink F, green B, orange P). These reactions are all the more remarkable given that any pair of these reagents do not react while the combination of all three reagents results in product formation. (Chemical Equation Presented) © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：4968 / 4971

页数：4

共 16 条

[1]

[Anonymous], 2001, ADV ORGANIC CHEM REA

[2] Pyridine and phosphine reactions with [CPh3][B(C6F5)4] [J].

Cabrera, Lourdes ;

Welch, Gregory C. ;

Masuda, Jason D. ;

Wei, Pingrong ;

Stephan, Douglas W. .

INORGANICA CHIMICA ACTA, 2006, 359 (09) :3066-3071

[3]

Cotton F. A., 1999, Advanced Inorganic Chemistry

[4] Reaction of the Lewis acid tris(pentafluorophenyl)borane with a phosphorus ylide: Competition between adduct formation and electrophilic and nucleophilic aromatic substitution pathways [J].

Doring, S ;

Erker, G ;

Frohlich, R ;

Meyer, O ;

Bergander, K .

ORGANOMETALLICS, 1998, 17 (11) :2183-2187

[5] Widening the roof: Synthesis and characterization of new chiral C1-symmetric octahydrofluorenyl organolanthanide catalysts and their implementation in the stereoselective cyclizations of aminoalkenes and phosphinoalkenes [J].

Douglass, Michael R. ;

Ogasawara, Masamichi ;

Hong, Sukwon ;

Metz, Matthew V. ;

Marks, Tobin J. .

Organometallics, 2002, 21 (02) :283-292

[6] Organolanthanide-catalyzed intramolecular hydrophosphination/cyclization of phosphinoalkenes and phosphinoalkynes [J].

Douglass, MR ;

Marks, TJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (08) :1824-1825

[7] Van der Waals complexes between unsaturated hydrocarbons and boron trifluoride: An infrared and ab initio study of ethene center dot BF3 and propene center dot BF3 [J].

Herrebout, WA ;

vanderVeken, BJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) :10446-10454

[8]

Lewis G.N., 1923, Thermodynamics and the Free Energy of Chemical Substances

[9] A theoretical investigation of benzene-AlX3 and ethene-AlX3 (X = H, F, Cl) interactions [J].

Tarakeshwar, P ;

Kim, KS .

JOURNAL OF PHYSICAL CHEMISTRY A, 1999, 103 (45) :9116-9124

[10] Ab initio study of benzene-BX3 (X = H, F, Cl) interactions [J].

Tarakeshwar, P ;

Lee, SJ ;

Lee, JY ;

Kim, KS .

JOURNAL OF PHYSICAL CHEMISTRY B, 1999, 103 (01) :184-191

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