CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap

Lavallo, Vincent; Canac, Yves; Donnadieu, Bruno; Schoeller, Wolfgang; Bertrand, Guy

CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap

Lavallo V, Canac Y, Donnadieu B, Schoeller W, Bertrand G (2006)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45(21): 3488-3491.

Zeitschriftenaufsatz | Veröffentlicht | Englisch

Download

Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!

DOI

https://doi.org/10.1002/anie.200600987

Autor*in

Lavallo, Vincent; Canac, Yves; Donnadieu, Bruno; Schoeller, Wolfgang^UniBi; Bertrand, Guy

Einrichtung

Fakultät für Chemie > Theoretische Chemie

Stichworte

carbon monoxide fixation; carbenes; ketenes; optical properties; radicals

Erscheinungsjahr

2006

Zeitschriftentitel

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Band

45

Ausgabe

21

Seite(n)

3488-3491

ISSN

1433-7851

eISSN

1521-3773

Page URI

https://pub.uni-bielefeld.de/record/1599117

Zitieren

Lavallo V, Canac Y, Donnadieu B, Schoeller W, Bertrand G. CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2006;45(21):3488-3491.

Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., & Bertrand, G. (2006). CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 45(21), 3488-3491. https://doi.org/10.1002/anie.200600987

Lavallo, Vincent, Canac, Yves, Donnadieu, Bruno, Schoeller, Wolfgang, and Bertrand, Guy. 2006. “CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45 (21): 3488-3491.

Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., and Bertrand, G. (2006). CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45, 3488-3491.

Lavallo, V., et al., 2006. CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 45(21), p 3488-3491.

V. Lavallo, et al., “CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 45, 2006, pp. 3488-3491.

Lavallo, V., Canac, Y., Donnadieu, B., Schoeller, W., Bertrand, G.: CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 45, 3488-3491 (2006).

Lavallo, Vincent, Canac, Yves, Donnadieu, Bruno, Schoeller, Wolfgang, and Bertrand, Guy. “CO fixation to stable acyclic and cyclic alkyl amino carbenes: Stable amino ketenes with a small HOMO-LUMO gap”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45.21 (2006): 3488-3491.

Daten bereitgestellt von European Bioinformatics Institute (EBI)

66 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Functional Disilenes in Synthesis.
Rammo A, Scheschkewitz D., Chemistry 24(27), 2018
PMID: 29193341

Reaction of B2 (o-tol)4 with CO and Isocyanides: Cleavage of the C≡O Triple Bond and Direct C-H Borylations.
Katsuma Y, Tsukahara N, Wu L, Lin Z, Yamashita M., Angew Chem Int Ed Engl 57(21), 2018
PMID: 29573087

Electrophilic Formylation of Arenes by Silylium Ion Mediated Activation of Carbon Monoxide.
Omann L, Qu ZW, Irran E, Klare HFT, Grimme S, Oestreich M., Angew Chem Int Ed Engl 57(27), 2018
PMID: 29741219

Coumaraz-2-on-4-ylidene: Ambiphilic N-Heterocyclic Carbenes with a Tunable Electronic Structure.
Song H, Kim H, Lee E., Angew Chem Int Ed Engl 57(28), 2018
PMID: 29767421

The Transition-Metal-Like Behavior of B2 (NHC)2 in the Activation of CO: HOMO-LUMO Swap Without Photoinduction.
Zhang H, Cao Z, Wu W, Mo Y., Angew Chem Int Ed Engl 57(40), 2018
PMID: 30084124

Cyclic (Alkyl)(amino)carbenes (CAACs): Recent Developments.
Melaimi M, Jazzar R, Soleilhavoup M, Bertrand G., Angew Chem Int Ed Engl 56(34), 2017
PMID: 28376253

Electronic and Ligand Properties of Skeletally Substituted Cyclic (Alkyl)(Amino)Carbenes (CAACs) and Their Reactivity towards Small Molecule Activation: A Theoretical Study.
Bharadwaz P, Chetia P, Phukan AK., Chemistry 23(41), 2017
PMID: 28504835

Borylenes: An Emerging Class of Compounds.
Soleilhavoup M, Bertrand G., Angew Chem Int Ed Engl 56(35), 2017
PMID: 28577325

Reactivity of a Dihydrodiborene with CO: Coordination, Insertion, Cleavage, and Spontaneous Formation of a Cyclic Alkyne.
Arrowsmith M, Böhnke J, Braunschweig H, Celik MA., Angew Chem Int Ed Engl 56(45), 2017
PMID: 28892234

Synthesis of P2C2O2 and P2CO via NHC-mediated coupling of the phosphaethynolate anion.
Gilliard RJ, Suter R, Schrader E, Benkő Z, Rheingold AL, Grützmacher H, Protasiewicz JD., Chem Commun (Camb) 53(91), 2017
PMID: 29095454

Isolation, structure and reactivity of a scandium boryl oxycarbene complex.
Wang B, Kang X, Nishiura M, Luo Y, Hou Z., Chem Sci 7(1), 2016
PMID: 28966773

Silicon based radicals, radical ions, diradicals and diradicaloids.
Chandra Mondal K, Roy S, Roesky HW., Chem Soc Rev 45(4), 2016
PMID: 26585359

Exploring the reducing role of boron: added insights from theory.
Dangat Y, Vanka K., Dalton Trans 45(14), 2016
PMID: 26619156

25 years of N-heterocyclic carbenes: activation of both main-group element-element bonds and NHCs themselves.
Würtemberger-Pietsch S, Radius U, Marder TB., Dalton Trans 45(14), 2016
PMID: 26675582

Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO.
Batsanov AS, Cabeza JA, Crestani MG, Fructos MR, García-Álvarez P, Gille M, Lin Z, Marder TB., Angew Chem Int Ed Engl 55(15), 2016
PMID: 26953905

A cyclic (alkyl)(amido)carbene: synthesis, study and utility as a desulfurization reagent.
McCarty ZR, Lastovickova DN, Bielawski CW., Chem Commun (Camb) 52(31), 2016
PMID: 27010415

Alkali Metal Carbenoids: A Case of Higher Stability of the Heavier Congeners.
Molitor S, Gessner VH., Angew Chem Int Ed Engl 55(27), 2016
PMID: 27100278

Cyclic (Alkyl)(Amino)Carbene Complexes of Rhodium and Nickel and Their Steric and Electronic Parameters.
Paul US, Sieck C, Haehnel M, Hammond K, Marder TB, Radius U., Chemistry 22(31), 2016
PMID: 27362629

Chemically Non-Innocent Cyclic (Alkyl)(Amino)Carbenes: Ligand Rearrangement, C-H and C-F Bond Activation.
Turner ZR., Chemistry 22(32), 2016
PMID: 27363588

Basic Reactivity Pattern of a Cyclic Disilylated Germylene.
Walewska M, Hlina J, Baumgartner J, Müller T, Marschner C., Organometallics 35(16), 2016
PMID: 27570360

Activation of C-F bonds in fluoroarenes by N-heterocyclic carbenes as an effective route to synthesize abnormal NHC complexes.
Kim Y, Lee E., Chem Commun (Camb) 52(72), 2016
PMID: 27533338

An air-persistent oxyallyl radical cation with simple di(methyl)amino substituents.
Regnier V, Molton F, Philouze C, Martin D., Chem Commun (Camb) 52(76), 2016
PMID: 27722255

Carbon dioxide cleavage across a tungsten-alkylidyne bearing a trianionic pincer-type ligand.
Gonsales SA, Ghiviriga I, Abboud KA, Veige AS., Dalton Trans 45(40), 2016
PMID: 27251426

Reactivity of a stable phosphinonitrene towards small molecules.
Dielmann F, Bertrand G., Chemistry 21(1), 2015
PMID: 25395098

Addition of ethylene or hydrogen to a main-group metal cluster under mild conditions.
Vasko P, Wang S, Tuononen HM, Power PP., Angew Chem Int Ed Engl 54(12), 2015
PMID: 25631067

Crystalline Cyclic (Alkyl)(amino)carbene-tetrafluoropyridyl Radical.
Styra S, Melaimi M, Moore CE, Rheingold AL, Augenstein T, Breher F, Bertrand G., Chemistry 21(23), 2015
PMID: 25925367

Synthesis, Characterization, and Theoretical Investigation of Two-Coordinate Palladium(0) and Platinum(0) Complexes Utilizing π-Accepting Carbenes.
Roy S, Mondal KC, Meyer J, Niepötter B, Köhler C, Herbst-Irmer R, Stalke D, Dittrich B, Andrada DM, Frenking G, Roesky HW., Chemistry 21(26), 2015
PMID: 25940809

Multiple complexation of CO and related ligands to a main-group element.
Braunschweig H, Dewhurst RD, Hupp F, Nutz M, Radacki K, Tate CW, Vargas A, Ye Q., Nature 522(7556), 2015
PMID: 26085273

Reductive Cleavage of Carbon Monoxide by a Disilenide.
Majumdar M, Omlor I, Yildiz CB, Azizoglu A, Huch V, Scheschkewitz D., Angew Chem Int Ed Engl 54(30), 2015
PMID: 26088688

Group 1 and 2 cyclic (alkyl)(amino)carbene complexes.
Turner ZR, Buffet JC., Dalton Trans 44(29), 2015
PMID: 26133112

Annulated boron substituted N-heterocyclic carbenes: theoretical prediction of highly electrophilic carbenes.
Bharadwaz P, Borthakur B, Phukan AK., Dalton Trans 44(42), 2015
PMID: 26455836

Cyclic (Amino)(aryl)carbenes (CAArCs) as Strong σ-Donating and π-Accepting Ligands for Transition Metals.
Rao B, Tang H, Zeng X, Liu L, Melaimi M, Bertrand G., Angew Chem Int Ed Engl 54(49), 2015
PMID: 26457345

Silver-Catalyzed Amidiniumation of Alkynes: Isolation of a Silver Intermediate, Synthesis of Enamine Amido Carbene Precursors, and an Unprecedented Umpolung of Propiolamide.
Lv S, Wang J, Zhang C, Xu S, Shi M, Zhang J., Angew Chem Int Ed Engl 54(49), 2015
PMID: 26473976

In pursuit of negative Fukui functions: molecules with very small band gaps.
Echegaray E, Rabi S, Cárdenas C, Zadeh FH, Rabi N, Lee S, Anderson JS, Toro-Labbe A, Ayers PW., J Mol Model 20(3), 2014
PMID: 24573501

C4 cumulene and the corresponding air-stable radical cation and dication.
Li Y, Mondal KC, Samuel PP, Zhu H, Orben CM, Panneerselvam S, Dittrich B, Schwederski B, Kaim W, Mondal T, Koley D, Roesky HW., Angew Chem Int Ed Engl 53(16), 2014
PMID: 24623450

Recent advances in carbon dioxide capture, fixation, and activation by using N-heterocyclic carbenes.
Yang L, Wang H., ChemSusChem 7(4), 2014
PMID: 24644039

Synthesis and characterization of a triphenyl-substituted radical and an unprecedented formation of a carbene-functionalized quinodimethane.
Mondal KC, Samuel PP, Roesky HW, Niepötter B, Herbst-Irmer R, Stalke D, Ehret F, Kaim W, Maity B, Koley D., Chemistry 20(30), 2014
PMID: 24664879

Diborabutatriene: an electron-deficient cumulene.
Böhnke J, Braunschweig H, Ewing WC, Hörl C, Kramer T, Krummenacher I, Mies J, Vargas A., Angew Chem Int Ed Engl 53(34), 2014
PMID: 24864006

One-, two-, and three-electron reduction of a cyclic alkyl(amino)carbene-SbCl₃ adduct.
Kretschmer R, Ruiz DA, Moore CE, Rheingold AL, Bertrand G., Angew Chem Int Ed Engl 53(31), 2014
PMID: 24961494

Isolation of a bis(oxazol-2-ylidene)-phenylborylene adduct and its reactivity as a boron-centered nucleophile.
Kong L, Li Y, Ganguly R, Vidovic D, Kinjo R., Angew Chem Int Ed Engl 53(35), 2014
PMID: 24980138

Azavinylidenephosphoranes: a class of cyclic push-pull carbenes.
Lavigne F, El Kazzi A, Escudié Y, Maerten E, Kato T, Saffon-Merceron N, Branchadell V, Cossío FP, Baceiredo A., Chemistry 20(39), 2014
PMID: 25123091

Synthesis and reactivity of a CAAC-aminoborylene adduct: a hetero-allene or an organoboron isoelectronic with singlet carbenes.
Dahcheh F, Martin D, Stephan DW, Bertrand G., Angew Chem Int Ed Engl 53(48), 2014
PMID: 25267591

Sydnone anions and abnormal N-heterocyclic carbenes of O-ethylsydnones. Characterizations, calculations and catalyses.
Wiechmann S, Freese T, Drafz MH, Hübner EG, Namyslo JC, Nieger M, Schmidt A., Chem Commun (Camb) 50(80), 2014
PMID: 25156208

31P NMR chemical shifts of carbene-phosphinidene adducts as an indicator of the π-accepting properties of carbenes.
Back O, Henry-Ellinger M, Martin CD, Martin D, Bertrand G., Angew Chem Int Ed Engl 52(10), 2013
PMID: 23364832

An air-stable oxyallyl radical cation.
Martin D, Moore CE, Rheingold AL, Bertrand G., Angew Chem Int Ed Engl 52(27), 2013
PMID: 23720417

Isolation of neutral mono- and dinuclear gold complexes of cyclic (alkyl)(amino)carbenes.
Weinberger DS, Melaimi M, Moore CE, Rheingold AL, Frenking G, Jerabek P, Bertrand G., Angew Chem Int Ed Engl 52(34), 2013
PMID: 23861304

Carbene-Stabilized Main Group Radicals and Radical Ions.
Martin CD, Soleilhavoup M, Bertrand G., Chem Sci 4(8), 2013
PMID: 23878717

Formation of trichlorosilyl-substituted carbon-centered stable radicals through the use of π-accepting carbenes.
Mondal KC, Roesky HW, Stückl AC, Ehret F, Kaim W, Dittrich B, Maity B, Koley D., Angew Chem Int Ed Engl 52(45), 2013
PMID: 24038666

1,2,4-Triazol-3-ylidenes with an N-2,4-dinitrophenyl substituent as strongly π-accepting N-heterocyclic carbenes.
Sato T, Hirose Y, Yoshioka D, Shimojo T, Oi S., Chemistry 19(46), 2013
PMID: 24591248

Metal-free binding and coupling of carbon monoxide at a boron-boron triple bond.
Braunschweig H, Dellermann T, Dewhurst RD, Ewing WC, Hammond K, Jimenez-Halla JO, Kramer T, Krummenacher I, Mies J, Phukan AK, Vargas A., Nat Chem 5(12), 2013
PMID: 24256866

The ambivalent chemistry of a free anionic N-heterocyclic carbene decorated with a malonate backbone: the plus of a negative charge.
César V, Labat S, Miqueu K, Sotiropoulos JM, Brousses R, Lugan N, Lavigne G., Chemistry 19(50), 2013
PMID: 24307368

Carbonylation of cyclotrisilenes.
Cowley MJ, Ohmori Y, Huch V, Ichinohe M, Sekiguchi A, Scheschkewitz D., Angew Chem Int Ed Engl 52(50), 2013
PMID: 24307015

Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes.
Queval P, Jahier C, Rouen M, Artur I, Legeay JC, Falivene L, Toupet L, Crévisy C, Cavallo L, Baslé O, Mauduit M., Angew Chem Int Ed Engl 52(52), 2013
PMID: 24307237

Expanding the chemistry of cationic N-heterocyclic carbenes: alternative synthesis, reactivity, and coordination chemistry.
Hildebrandt B, Raub S, Frank W, Ganter C., Chemistry 18(21), 2012
PMID: 22473860

Synthesis, structure, and reactivity of a monomeric iminoalane.
Li J, Li X, Huang W, Hu H, Zhang J, Cui C., Chemistry 18(48), 2012
PMID: 23129126

Insights into the carbene-initiated aggregation of [Fe(cot)(2)].
Lavallo V, El-Batta A, Bertrand G, Grubbs RH., Angew Chem Int Ed Engl 50(1), 2011
PMID: 21110365

Stable singlet carbenes as mimics for transition metal centers.
Martin D, Soleilhavoup M, Bertrand G., Chem Sci 2(3), 2011
PMID: 21743834

Synthesis and characterization of a neutral tricoordinate organoboron isoelectronic with amines.
Kinjo R, Donnadieu B, Celik MA, Frenking G, Bertrand G., Science 333(6042), 2011
PMID: 21798945

Grubbs and Hoveyda-Type Ruthenium Complexes Bearing a Cyclic Bent-Allene.
Dehope A, Donnadieu B, Bertrand G., J Organomet Chem 696(17), 2011
PMID: 21765542

Isolation of crystalline carbene-stabilized P(2)-radical cations and P(2)-dications.
Back O, Donnadieu B, Parameswaran P, Frenking G, Bertrand G., Nat Chem 2(5), 2010
PMID: 20414236

Isolation of a carbene-stabilized phosphorus mononitride and its radical cation (PN+*).
Kinjo R, Donnadieu B, Bertrand G., Angew Chem Int Ed Engl 49(34), 2010
PMID: 20632430

Activation of Si-H, B-H, and P-H bonds at a single nonmetal center.
Frey GD, Masuda JD, Donnadieu B, Bertrand G., Angew Chem Int Ed Engl 49(49), 2010
PMID: 21031393

Synthesis of a simplified version of stable bulky and rigid cyclic (alkyl)(amino)carbenes, and catalytic activity of the ensuing gold(I) complex in the three-component preparation of 1,2-dihydroquinoline derivatives.
Zeng X, Frey GD, Kinjo R, Donnadieu B, Bertrand G., J Am Chem Soc 131(24), 2009
PMID: 19456108

Chemical bonding: Rethinking carbon.
Dyker CA, Bertrand G., Nat Chem 1(4), 2009
PMID: 21378867

Stable Bis(diisopropylamino)cyclopropenylidene (BAC) as Ligand for Transition Metal Complexes.
Kuchenbeiser G, Donnadieu B, Bertrand G., J Organomet Chem 693(5), 2008
PMID: 19255609

Cyclic (Alkyl)(amino)carbene Gold(I) complexes: A Synthetic and Structural Investigation.
Frey GD, Dewhurst RD, Kousar S, Donnadieu B, Bertrand G., J Organomet Chem 693(8-9), 2008
PMID: 19343084

26 References

Daten bereitgestellt von Europe PubMed Central.

AUTHOR UNKNOWN, 2004

Gomberg M., 1900

AUTHOR UNKNOWN, 0

Staudinger H., 1905

McAllister MA, Tidwell TT., 1994

AUTHOR UNKNOWN, 0

Sander W, Hubert R, Kraka E, Grafenstein J, Cremer D., 2000

Ammann JR, Subramanian R, Sheridan RS., 1992

Lyashchuk SN, Skrypnik YG., 1994

Dixon DA, Arduengo AJ, Dobbs KD, Khasnis DV., 1995

Synthesis, reactivity, and ligand properties of a stable alkyl carbene.
Lavallo V, Mafhouz J, Canac Y, Donnadieu B, Schoeller WW, Bertrand G., J. Am. Chem. Soc. 126(28), 2004
PMID: 15250717

Lavallo V, Canac Y, Prasang C, Donnadieu B, Bertrand G., 2005

AUTHOR UNKNOWN, 0

Martin D, Baceiredo A, Gornitzka H, Schoeller WW, Bertrand G., 2005

AUTHOR UNKNOWN, 0

Seikaly HR, Tidwell TT., 1986

Arendale WF, Fletcher WH., 1956

Nadzhimutdinov S, Slovokhotova NA, Kargin VA, Cherneva EP, Cherbukov YA., 1957

Perepichka DE, Bryce MR., 2005

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB