A Unique Frustrated Lewis Pair Pathway to Remarkably Stable Borata-Alkene Systems

被引：38

作者：

Yu, Jiangang ^{[1
]}

Kehr, Gerald ^{[1
]}

Daniliuc, Constantin G. ^{[1
]}

Erker, Gerhard ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY | 2013年 / 19期

基金：

欧洲研究理事会;

关键词：

Borata-alkenes; Lewis acids; Lewis bases; Boron; Phosphorus; BORON-STABILIZED CARBANIONS; RAY CRYSTAL-STRUCTURE; GAS-PHASE; 1,1-CARBOBORATION; ANIONS; 1,1-ORGANOBORATION; ACTIVATION; LIGANDS; LITHIUM; BOND;

D O I：

10.1002/ejic.201300520

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The hydroboration of a conjugated diphenylphosphanylenyne with Piers' borane [HB(C6F5)2] gives three products. The major product is probably formed by generation of a geminal P/B frustrated Lewis pair that undergoes rapid and subsequent intramolecular conjugate addition of the phosphane to the dienyl borane unit to yield a unique phosphonium borata-diene. The minor products originate from alternative regioisomeric hydroboration reactions. Two examples of the new phosphonium borata-olefin products were characterized by X-ray diffraction.

引用

页码：3312 / 3315

页数：4

共 35 条

[1] The Pentaphenylborole-2,6-Lutidine Adduct: A System with Unusual Thermochromic and Photochromic Properties [J].

Ansorg, Kay ;

Braunschweig, Holger ;

Chiu, Ching-Wen ;

Engels, Bernd ;

Gamon, Daniela ;

Huegel, Markus ;

Kupfer, Thomas ;

Radacki, Krzysztof .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (12) :2833-2836

[2] 1-PHENYLBORABENZENE ANION [J].

ASHE, AJ ;

SHU, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (07) :1804-&

[3] X-RAY CRYSTAL-STRUCTURE OF THE BORON-STABILIZED CARBANION - [LI(12-CROWN-4)2][CH2C6H2(3,5-ME2)(4-B(2,4,6-ME3C6H2)2)].ET2O - EVIDENCE FOR BORON YLIDE CHARACTER [J].

BARTLETT, RA ;

POWER, PP .

ORGANOMETALLICS, 1986, 5 (09) :1916-1917

[4] 1,1-Carboboration of 1-Alkynes: A Conceptual Alternative to the Hydroboration Reaction [J].

Chen, Chao ;

Voss, Tanja ;

Froehlich, Roland ;

Kehr, Gerald ;

Erker, Gerhard .

ORGANIC LETTERS, 2011, 13 (01) :62-65

[5] Carbon-Carbon Bond Activation by 1,1-Carboboration of Internal Alkynes [J].

Chen, Chao ;

Kehr, Gerald ;

Froehlich, Roland ;

Erker, Gerhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (39) :13594-13595

[6] Structural changes accompanying the stepwise population of a B-C π bond [J].

Chiu, Ching-Wen ;

Gabbaie, Francois P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) :6878-6881

[7]

Cowley A. H., 1994, ANGEW CHEM, V106, P584

[8]

Eisch J.J., 1996, Adv. Organomet. Chem, V39, P355

[9] Phosphirenium-borate zwitterion: formation in the 1,1-carboboration reaction of phosphinylalkynes [J].

Ekkert, Olga ;

Kehr, Gerald ;

Froehlich, Roland ;

Erker, Gerhard .

CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10482-10484

[10] P-C Bond Activation Chemistry: Evidence for 1,1-Carboboration Reactions Proceeding with Phosphorus-Carbon Bond Cleavage [J].

Ekkert, Olga ;

Kehr, Gerald ;

Froehlich, Roland ;

Erker, Gerhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (12) :4610-4616

← 1 2 3 4 →