A computational perspective of olefins metathesis catalyzed by N-heterocyclic carbene ruthenium (pre) catalysts

被引：60

作者：

Credendino, Raffaele ^{[1
]}

Poater, Albert ^{[2
]}

Ragone, Francesco ^{[1
]}

Cavallo, Luigi ^{[1
]}

机构：

[1] Univ Salerno, Dept Biol & Chem, I-84084 Fisciano, Italy

[2] Univ Girona, Catalan Inst Water Res ICRA, E-17003 Girona, Spain

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2011年 / 1卷 / 08期

关键词：

RING-CLOSING METATHESIS; OPENING CROSS-METATHESIS; COMPLEXES RELEVANT; ENYNE METATHESIS; THEORETICAL PERSPECTIVE; INTERMEDIATES RELEVANT; COUPLING REACTIONS; GRUBBS RUTHENIUM; ARYL SUBSTITUENT; LIGANDS;

D O I：

10.1039/c1cy00052g

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

In recent years olefin metathesis catalyzed by N-heterocyclic carbene ruthenium complexes has attracted remarkable attention as a versatile tool to form new C=C bonds. The last developed (pre)catalysts show excellent performances, and this achievement has been possible because of continuous experimental and computational efforts to understand the laws controlling the behavior of these systems. This perspective rapidly traces the ideas and discoveries that computational chemistry contributed to the development of these catalysts, with particular emphasis on catalysts presenting a N-heterocyclic carbene ligand.

引用

页码：1287 / 1297

页数：11

共 99 条

[1] Ruthenium-catalyzed olefin metathesis: A quantum molecular dynamics study [J].

Aagaard, OM ;

Meier, RJ ;

Buda, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7174-7182

[2] Mechanism and activity of ruthenium olefin metathesis catalysts: The role of ligands and substrates from a theoretical perspective [J].

Adlhart, C ;

Chen, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3496-3510

[3] Mechanistic studies of olefin metathesis by ruthenium carbene complexes using electrospray ionization tandem mass spectrometry [J].

Adlhart, C ;

Hinderling, C ;

Baumann, H ;

Chen, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (34) :8204-8214

[4] Model compounds of ruthenium-alkene intermediates in olefin metathesis reactions [J].

Anderson, Donde R. ;

Hickstein, Daniel D. ;

O'Leary, Daniel J. ;

Grubbs, Robert H. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (26) :8386-8387

[5] Kinetic selectivity of olefin metathesis catalysts bearing cyclic (alkyl)(amino)carbenes [J].

Anderson, Donde R. ;

Ung, Thay ;

Mkrtumyan, Garik ;

Bertrand, Guy ;

Grubbs, Robert H. ;

Schrodi, Yann .

ORGANOMETALLICS, 2008, 27 (04) :563-566

[6] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[7] The intriguing modeling of cis-trans selectivity in ruthenium-catalyzed olefin metathesis [J].

Bahri-Laleh, Naeimeh ;

Credendino, Raffaele ;

Cavallo, Luigi .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 :40-45

[8] Mixed N-heterocyclic carbene/phosphite ruthenium complexes: towards a new generation of olefin metathesis catalysts [J].

Bantreil, Xavier ;

Schmid, Thibault E. ;

Randall, Rebecca A. M. ;

Slawin, Alexandra M. Z. ;

Cazin, Catherine S. J. .

CHEMICAL COMMUNICATIONS, 2010, 46 (38) :7115-7117

[9] Is the Hoveyda-Grubbs Complex a Vinylogous Fischer-Type Carbene? Aromaticity-Controlled Activity of Ruthenium Metathesis Catalysts [J].

Barbasiewicz, Michal ;

Szadkowska, Anna ;

Makal, Anna ;

Jarzembska, Katarzyna ;

Wozniak, Krzysztof ;

Grela, Karol .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (30) :9330-9337

[10] Structure and activity peculiarities of ruthenium quinoline and quinoxaline complexes: Novel metathesis catalysts [J].

Barbasiewicz, Michal ;

Szadkowska, Anna ;

Bujok, Robert ;

Grela, Karol .

ORGANOMETALLICS, 2006, 25 (15) :3599-3604

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