Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes

Ghadwal R (2016)
DALTON TRANSACTIONS 45(41): 16081-16095.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
DOI
Autor*in
Ghadwal, RajendraUniBi
Einrichtung
Fakultät für Chemie > Anorganische Chemie und Strukturchemie
Abstract / Bemerkung
N-Heterocyclic carbenes (NHCs) are an important class of compounds that are indeed regarded as most versatile carbon-donor ligands in transition metal and organometallic catalysis. In addition, NHCs are also capable of stabilizing a variety of highly reactive main group compounds with intriguing properties. The enormous success of NHCs prompted the investigation of other carbon-based neutral ligands with additional structural and electronic features. Reactivity studies of NHCs and their complexes unveiled routes to new carbon donor ligands. Such NHC-derived ligands can be grouped into three categories: (i) N-heterocyclic olefins (the donor site is extended by an intervening carbon atom), (ii) ditopic carbanionic-NHCs (an additional coordination site is generated by the deprotonation of an NHC), and (iii) abnormal-NHCs (the carbene center of an NHC is moved to different positions). This article summarizes the recent advances in NHC chemistry of compounds featuring the aforementioned ligands, which are exclusively derived by the functionalization of NHCs, 1,3-bis(2,6-diisopropylphenyl) imidazol-2-ylidene (IPr) in particular.
Erscheinungsjahr
2016
Zeitschriftentitel
DALTON TRANSACTIONS
Band
45
Ausgabe
41
Seite(n)
16081-16095
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2907043

Zitieren

Ghadwal R. Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes. DALTON TRANSACTIONS. 2016;45(41):16081-16095.
Ghadwal, R. (2016). Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes. DALTON TRANSACTIONS, 45(41), 16081-16095. doi:10.1039/c6dt02158a
Ghadwal, Rajendra. 2016. “Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes”. DALTON TRANSACTIONS 45 (41): 16081-16095.
Ghadwal, R. (2016). Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes. DALTON TRANSACTIONS 45, 16081-16095.
Ghadwal, R., 2016. Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes. DALTON TRANSACTIONS, 45(41), p 16081-16095.
R. Ghadwal, “Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes”, DALTON TRANSACTIONS, vol. 45, 2016, pp. 16081-16095.
Ghadwal, R.: Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes. DALTON TRANSACTIONS. 45, 16081-16095 (2016).
Ghadwal, Rajendra. “Carbon-based two electron sigma-donor ligands beyond classical N-heterocyclic carbenes”. DALTON TRANSACTIONS 45.41 (2016): 16081-16095.

17 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

A vinyl silylsilylene and its activation of strong homo- and heteroatomic bonds.
Roy MMD, Ferguson MJ, McDonald R, Zhou Y, Rivard E., Chem Sci 10(26), 2019
PMID: 31341599
Silylene-Functionalized N-Heterocyclic Carbene (Si-NHC).
Rottschäfer D, Blomeyer S, Neumann B, Stammler HG, Ghadwal RS., Chemistry 24(2), 2018
PMID: 28833705
The Viability of C5-Protonated- and C4,C5-Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry.
Rottschäfer D, Ebeler F, Strothmann T, Neumann B, Stammler HG, Mix A, Ghadwal RS., Chemistry 24(15), 2018
PMID: 29363830
Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes.
Rottschäfer D, Neumann B, Stammler HG, van Gastel M, Andrada DM, Ghadwal RS., Angew Chem Int Ed Engl 57(17), 2018
PMID: 29465816
N-Heterocyclic Carbene Analogues of Thiele and Chichibabin Hydrocarbons.
Rottschäfer D, Ho NKT, Neumann B, Stammler HG, van Gastel M, Andrada DM, Ghadwal RS., Angew Chem Int Ed Engl 57(20), 2018
PMID: 29668119
Oxidative Coupling of Anionic Abnormal N-Heterocyclic Carbenes: Efficient Access to Janus-Type 4,4'-Bis(2H-imidazol-2-ylidene)s.
Grineva AA, Valyaev DA, César V, Filippov OA, Khrustalev VN, Nefedov SE, Lugan N., Angew Chem Int Ed Engl 57(27), 2018
PMID: 29528185
Synthesis of Azo Dyes from Mesoionic Carbenes and Nitrous Oxide.
Eymann LYM, Scopelliti R, Tirani FF, Severin K., Chemistry 24(31), 2018
PMID: 29756660
Purine-substituted imidazolium mesomeric betaines and their tautomeric N-heterocyclic carbenes. Formation of a cyclic borane adduct.
Zhang J, Hübner EG, Namyslo JC, Nieger M, Schmidt A., Org Biomol Chem 16(36), 2018
PMID: 30203828
Azido- and amido-substituted gallium hydrides supported by N-heterocyclic carbenes.
Swarnakar AK, Ferguson MJ, McDonald R, Rivard E., Dalton Trans 46(5), 2017
PMID: 28074197
Fixation of nitrous oxide by mesoionic and carbanionic N-heterocyclic carbenes.
Eymann LY, Scopelliti R, Fadaei FT, Cecot G, Solari E, Severin K., Chem Commun (Camb) 53(31), 2017
PMID: 28367569
C4-Ferrocenylsilyl-bridged and -substituted N-heterocyclic carbenes: complexation of germanium chloride.
Wang Y, Hickox HP, Wei P, Robinson GH., Dalton Trans 46(17), 2017
PMID: 28229146
Engaging dual donor sites within an N-heterocyclic olefin phosphine ligand.
Lui MW, Shynkaruk O, Oakley MS, Sinelnikov R, McDonald R, Ferguson MJ, Meldrum A, Klobukowski M, Rivard E., Dalton Trans 46(18), 2017
PMID: 28418418
Calcium Hydride Reactivity: Formation of an Anionic N-Heterocyclic Olefin Ligand.
Causero A, Elsen H, Pahl J, Harder S., Angew Chem Int Ed Engl 56(24), 2017
PMID: 28474850
Organocatalytic hydroborylation promoted by N-heterocyclic olefins.
Hering-Junghans C, Watson IC, Ferguson MJ, McDonald R, Rivard E., Dalton Trans 46(22), 2017
PMID: 28518206
Facile routes to abnormal-NHC-cobalt(ii) complexes.
Ghadwal RS, Lamm JH, Rottschäfer D, Schürmann CJ, Demeshko S., Dalton Trans 46(24), 2017
PMID: 28573296
Normal-to-abnormal rearrangement of an N-heterocyclic carbene with a silylene transition metal complex.
Ghadwal RS, Rottschäfer D, Andrada DM, Frenking G, Schürmann CJ, Stammler HG., Dalton Trans 46(24), 2017
PMID: 28590484
N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid.
Rottschäfer D, Neumann B, Stammler HG, Ghadwal RS., Chemistry 23(38), 2017
PMID: 28556982

165 References

Daten bereitgestellt von Europe PubMed Central.

Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.
Bruno NC, Tudge MT, Buchwald SL., Chem Sci 4(), 2013
PMID: 23667737
Deactivation in homogeneous transition metal catalysis: causes, avoidance, and cure.
Crabtree RH., Chem. Rev. 115(1), 2014
PMID: 25493420

Fourmy, Catal. Sci. Technol. 5(), 2015
Metal-ligand cooperation.
Khusnutdinova JR, Milstein D., Angew. Chem. Int. Ed. Engl. 54(42), 2015
PMID: 26436516
Cyclic (alkyl)(amino)carbenes (CAACs): stable carbenes on the rise.
Soleilhavoup M, Bertrand G., Acc. Chem. Res. 48(2), 2014
PMID: 25515548
Carbene-Stabilized Main Group Radicals and Radical Ions.
Martin CD, Soleilhavoup M, Bertrand G., Chem Sci 4(8), 2013
PMID: 23878717
A Brief Survey of our Contribution to Stable Carbene Chemistry.
Martin D, Melaimi M, Soleilhavoup M, Bertrand G., Organometallics 30(20), 2011
PMID: 22707843
Quantifying and understanding the electronic properties of N-heterocyclic carbenes.
Nelson DJ, Nolan SP., Chem Soc Rev 42(16), 2013
PMID: 23788114
N-heterocyclic carbenes in late transition metal catalysis.
Diez-Gonzalez S, Marion N, Nolan SP., Chem. Rev. 109(8), 2009
PMID: 19588961
An overview of N-heterocyclic carbenes.
Hopkinson MN, Richter C, Schedler M, Glorius F., Nature 510(7506), 2014
PMID: 24965649
The measure of all rings--N-heterocyclic carbenes.
Droge T, Glorius F., Angew. Chem. Int. Ed. Engl. 49(39), 2010
PMID: 20715233

Gaspar, 1985

Jones, 2005

Bertrand, 2005
Heterocyclic carbenes: synthesis and coordination chemistry.
Hahn FE, Jahnke MC., Angew. Chem. Int. Ed. Engl. 47(17), 2008
PMID: 18398856

Igau, Angew. Chem., Int. Ed. Engl. 28(), 1989

Wanzlick, Angew. Chem., Int. Ed. Engl. 7(), 1968

Öfele, J. Organomet. Chem. 12(), 1968

Arduengo, J. Am. Chem. Soc. 113(), 1991

Ranganath, Catal. Sci. Technol. 3(), 2013
N-Heterocyclic carbene chemistry of iron: fundamentals and applications.
Ingleson MJ, Layfield RA., Chem. Commun. (Camb.) 48(30), 2012
PMID: 22395151

AUTHOR UNKNOWN, 2011
N-heterocyclic carbenes in late transition metal catalysis.
Diez-Gonzalez S, Marion N, Nolan SP., Chem. Rev. 109(8), 2009
PMID: 19588961
N-heterocyclic carbenes: a new concept in organometallic catalysis.
Herrmann WA., Angew. Chem. Int. Ed. Engl. 41(8), 2002
PMID: 19750753
Dichlorosilylene: a high temperature transient species to an indispensable building block.
Ghadwal RS, Azhakar R, Roesky HW., Acc. Chem. Res. 46(2), 2012
PMID: 23181482
N-heterocyclic carbene-main-group chemistry: a rapidly evolving field.
Wang Y, Robinson GH., Inorg Chem 53(22), 2014
PMID: 25343222

Braunschweig, Organometallics 33(), 2014

Frenking, 2014
Donor-acceptor chemistry in the main group.
Rivard E., Dalton Trans 43(23), 2014
PMID: 24788390
Carbene-stabilized main group diatomic allotropes.
Wang Y, Robinson GH., Dalton Trans 41(2), 2011
PMID: 21904737
N-Heterocyclic carbene metal complexes: photoluminescence and applications.
Visbal R, Gimeno MC., Chem Soc Rev 43(10), 2014
PMID: 24604135
Covalent functionalization of graphene with reactive intermediates.
Park J, Yan M., Acc. Chem. Res. 46(1), 2012
PMID: 23116448

Norris, Macromolecules 43(), 2010

Bielawski, Prog. Polym. Sci. 32(), 2007
Towards electrically conductive, self-healing materials.
Williams KA, Boydston AJ, Bielawski CW., J R Soc Interface 4(13), 2007
PMID: 17251165

Chen, Chem. Mater. 18(), 2006
The use of the sterically demanding IPr* and related ligands in catalysis.
Izquierdo F, Manzini S, Nolan SP., Chem. Commun. (Camb.) 50(95), 2014
PMID: 25155373
Skeleton decoration of NHCs by amino groups and its sequential booster effect on the palladium-catalyzed Buchwald-Hartwig amination.
Zhang Y, Cesar V, Storch G, Lugan N, Lavigne G., Angew. Chem. Int. Ed. Engl. 53(25), 2014
PMID: 24801592

de, Coord. Chem. Rev. 253(), 2009

Diez-Gonzalez, Coord. Chem. Rev. 251(), 2007
A facile route to functionalized N-heterocyclic carbenes (NHCs) with NHC base-stabilized dichlorosilylene.
Ghadwal RS, Roesky HW, Granitzka M, Stalke D., J. Am. Chem. Soc. 132(29), 2010
PMID: 20608639
Synthesis of 4- and 4,5-functionalized imidazol-2-ylidenes from a single 4,5-unsubstituted imidazol-2-ylidene.
Mendoza-Espinosa D, Donnadieu B, Bertrand G., J. Am. Chem. Soc. 132(21), 2010
PMID: 20443633
Abnormal reactivity of an N-heterocyclic carbene (NHC) with a phosphaalkene: a route to a 4-phosphino-substituted NHC.
Bates JI, Kennepohl P, Gates DP., Angew. Chem. Int. Ed. Engl. 48(52), 2009
PMID: 19937891
Stability and electronic properties of imidazole-based mesoionic carbenes.
Ung G, Bertrand G., Chemistry 17(30), 2011
PMID: 21656597
Crystalline 1H-1,2,3-triazol-5-ylidenes: new stable mesoionic carbenes (MICs).
Guisado-Barrios G, Bouffard J, Donnadieu B, Bertrand G., Angew. Chem. Int. Ed. Engl. 49(28), 2010
PMID: 20509134
Palladium-catalyzed direct C2-arylation of an N-heterocyclic carbene: an atom-economic route to mesoionic carbene ligands.
Ghadwal RS, Reichmann SO, Herbst-Irmer R., Chemistry 21(11), 2015
PMID: 25639790

Arduengo, Angew. Chem., Int. Ed. 37(), 1998
Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex.
Grundemann S, Kovacevic A, Albrecht M, Faller JW, Crabtree RH., Chem. Commun. (Camb.) (21), 2001
PMID: 12240147
Percent buried volume for phosphine and N-heterocyclic carbene ligands: steric properties in organometallic chemistry.
Clavier H, Nolan SP., Chem. Commun. (Camb.) 46(6), 2010
PMID: 20107630

Crabtree, Coord. Chem. Rev. 257(), 2013
Beyond conventional N-heterocyclic carbenes: abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization.
Schuster O, Yang L, Raubenheimer HG, Albrecht M., Chem. Rev. 109(8), 2009
PMID: 19331408
Isolation of a C5-deprotonated imidazolium, a crystalline "abnormal" N-heterocyclic carbene.
Aldeco-Perez E, Rosenthal AJ, Donnadieu B, Parameswaran P, Frenking G, Bertrand G., Science 326(5952), 2009
PMID: 19900893

Uzelac, Chem. Sci. 6(), 2015
Normal-to-abnormal rearrangement and NHC activation in three-coordinate iron(II) carbene complexes.
Day BM, Pugh T, Hendriks D, Guerra CF, Evans DJ, Bickelhaupt FM, Layfield RA., J. Am. Chem. Soc. 135(36), 2013
PMID: 23978294

Lin, Coord. Chem. Rev. 251(), 2007

Kascatan-Nebioglu, Coord. Chem. Rev. 251(), 2007
Unexpected oxidative C-C cleavage in the metallation of 2-substituted imidazolium salts to give N-heterocyclic carbene complexes.
Chianese AR, Zeglis BM, Crabtree RH., Chem. Commun. (Camb.) (19), 2004
PMID: 15467859

Kuhn, J. Chem. Soc., Chem. Commun. (), 1993
A viable anionic N-heterocyclic dicarbene.
Wang Y, Xie Y, Abraham MY, Wei P, Schaefer HF 3rd, Schleyer Pv, Robinson GH., J. Am. Chem. Soc. 132(41), 2010
PMID: 20863065

Jana, Eur. J. Inorg. Chem. (), 2011

Rehbein, Chem. Sci. 6(), 2015
Recent advances in employing homoenolates generated by N-heterocyclic carbene (NHC) catalysis in carbon-carbon bond-forming reactions.
Menon RS, Biju AT, Nair V., Chem Soc Rev 44(15), 2015
PMID: 26014054
Umpolung by N-heterocyclic carbenes: generation and reactivity of the elusive 2,2-diamino enols (Breslow intermediates).
Berkessel A, Elfert S, Yatham VR, Neudorfl JM, Schlorer NE, Teles JH., Angew. Chem. Int. Ed. Engl. 51(49), 2012
PMID: 23081675
Organocatalytic umpolung: N-heterocyclic carbenes and beyond.
Bugaut X, Glorius F., Chem Soc Rev 41(9), 2012
PMID: 22377957

Breslow, J. Am. Chem. Soc. 80(), 1958
Coordination chemistry of ene-1,1-diamines and a prototype "carbodicarbene".
Furstner A, Alcarazo M, Goddard R, Lehmann CW., Angew. Chem. Int. Ed. Engl. 47(17), 2008
PMID: 18348113

Ghadwal, Eur. J. Inorg. Chem. 2014(), 2014

Powers, Polyhedron 108(), 2016
Synthesis and reactions of N-heterocyclic carbene boranes.
Curran DP, Solovyev A, Makhlouf Brahmi M, Fensterbank L, Malacria M, Lacote E., Angew. Chem. Int. Ed. Engl. 50(44), 2011
PMID: 21898724

Farrell, Chem. Sci. 6(), 2015
Hydrogenations at room temperature and atmospheric pressure with mesoionic carbene-stabilized borenium catalysts.
Eisenberger P, Bestvater BP, Keske EC, Crudden CM., Angew. Chem. Int. Ed. Engl. 54(8), 2015
PMID: 25586407

Matsumoto, Organometallics 28(), 2009
Mono- and di-cationic hydrido boron compounds.
Ghadwal RS, Schurmann CJ, Andrada DM, Frenking G., Dalton Trans 44(32), 2015
PMID: 26200103

Kronig, Eur. J. Inorg. Chem. 2013(), 2013
Donor-acceptor complexation and dehydrogenation chemistry of aminoboranes.
Malcolm AC, Sabourin KJ, McDonald R, Ferguson MJ, Rivard E., Inorg Chem 51(23), 2012
PMID: 23153209
Synthesis and luminescent properties of Lewis base-appended borafluorenes.
Berger CJ, He G, Merten C, McDonald R, Ferguson MJ, Rivard E., Inorg Chem 53(3), 2014
PMID: 24428809
Intercepting low oxidation state main group hydrides with a nucleophilic N-heterocyclic olefin.
Al-Rafia SM, Malcolm AC, Liew SK, Ferguson MJ, McDonald R, Rivard E., Chem. Commun. (Camb.) 47(24), 2011
PMID: 21562648

Ingleson, 2015
Cationic tricoordinate boron intermediates: borenium chemistry from the organic perspective.
De Vries TS, Prokofjevs A, Vedejs E., Chem. Rev. 112(7), 2012
PMID: 22519545
Borinium, borenium, and boronium ions: synthesis, reactivity, and applications.
Piers WE, Bourke SC, Conroy KD., Angew. Chem. Int. Ed. Engl. 44(32), 2005
PMID: 16086441
Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes.
Prokofjevs A, Boussonniere A, Li L, Bonin H, Lacote E, Curran DP, Vedejs E., J. Am. Chem. Soc. 134(29), 2012
PMID: 22713106
Pinacol boronates by direct arene borylation with borenium cations.
Del Grosso A, Singleton PJ, Muryn CA, Ingleson MJ., Angew. Chem. Int. Ed. Engl. 50(9), 2011
PMID: 21344561
Synthesis, structure, and reactivity of a dihydrido borenium cation.
Ines B, Patil M, Carreras J, Goddard R, Thiel W, Alcarazo M., Angew. Chem. Int. Ed. Engl. 50(36), 2011
PMID: 21761533
The elusive three-coordinate dicationic hydrido boron complex.
Chen WC, Lee CY, Lin BC, Hsu YC, Shen JS, Hsu CP, Yap GP, Ong TG., J. Am. Chem. Soc. 136(3), 2014
PMID: 24383448
A two-coordinate boron cation featuring C-B+-C bonding.
Shoji Y, Tanaka N, Mikami K, Uchiyama M, Fukushima T., Nat Chem 6(6), 2014
PMID: 24848235
Main-group chemistry: boron served straight up.
Reus C, Wagner M., Nat Chem 6(6), 2014
PMID: 24848230
A boron-boron coupling reaction between two ethyl cation analogues.
Litters S, Kaifer E, Enders M, Himmel HJ., Nat Chem 5(12), 2013
PMID: 24256867
Formation of N-heterocyclic, donor-stabilized borenium ions.
Someya CI, Inoue S, Prasang C, Irran E, Driess M., Chem. Commun. (Camb.) 47(23), 2011
PMID: 21519618
N-Directed aliphatic C-H borylation using borenium cation equivalents.
Prokofjevs A, Vedejs E., J. Am. Chem. Soc. 133(50), 2011
PMID: 22082151

Tsai, Organometallics 29(), 2010
Borenium cations derived from BODIPY dyes.
Bonnier C, Piers WE, Parvez M, Sorensen TS., Chem. Commun. (Camb.) (38), 2008
PMID: 18815694
Weakly stabilized primary borenium cations and their dicationic dimers.
Prokofjevs A, Kampf JW, Solovyev A, Curran DP, Vedejs E., J. Am. Chem. Soc. 135(42), 2013
PMID: 24087933
Synthesis and structure of a ferrocenylboron dication.
Braunschweig H, Kaupp M, Lambert C, Nowak D, Radacki K, Schinzel S, Uttinger K., Inorg Chem 47(17), 2008
PMID: 18671341
A beta-diketiminate-supported boron dication.
Vidovic D, Findlater M, Cowley AH., J. Am. Chem. Soc. 129(27), 2007
PMID: 17569541
Synthesis and structural characterization of a stable dimeric boron(II) dication.
Dinda R, Ciobanu O, Wadepohl H, Hubner O, Acharyya R, Himmel HJ., Angew. Chem. Int. Ed. Engl. 46(47), 2007
PMID: 17960743
Boron di- and tri-cations.
Vargas-Baca I, Findlater M, Powell A, Vasudevan KV, Cowley AH., Dalton Trans (45), 2008
PMID: 19002329

Reed, Chem. Rev. 88(), 1988

Reed, J. Chem. Phys. 83(), 1985
Dative bonds in main-group compounds: a case for more arrows!
Frenking G., Angew. Chem. Int. Ed. Engl. 53(24), 2014
PMID: 24849466

Wang, Organometallics 32(), 2013
A stable, neutral diborene containing a B=B double bond.
Wang Y, Quillian B, Wei P, Wannere CS, Xie Y, King RB, Schaefer HF 3rd, Schleyer PV, Robinson GH., J. Am. Chem. Soc. 129(41), 2007
PMID: 17887683
Planar, twisted, and trans-bent: conformational flexibility of neutral diborenes.
Wang Y, Quillian B, Wei P, Xie Y, Wannere CS, King RB, Schaefer HF 3rd, Schleyer PV, Robinson GH., J. Am. Chem. Soc. 130(11), 2008
PMID: 18288847

Solovyev, Organometallics 31(), 2012

Timms, Acc. Chem. Res. 6(), 1973

Pachaly, Angew. Chem., Int. Ed. Engl. 23(), 1984
Reactivity of borylenes toward ethyne, ethene, and methane.
Krasowska M, Bettinger HF., J. Am. Chem. Soc. 134(41), 2012
PMID: 23035732
The parent borylene: betwixt and between.
Curran DP, Boussonniere A, Geib SJ, Lacote E., Angew. Chem. Int. Ed. Engl. 51(7), 2012
PMID: 22311810
Trapping the elusive parent borylene.
Bissinger P, Braunschweig H, Kraft K, Kupfer T., Angew. Chem. Int. Ed. Engl. 50(20), 2011
PMID: 21495129
Generation of a carbene-stabilized bora-borylene and its insertion into a C-H bond.
Bissinger P, Braunschweig H, Damme A, Dewhurst RD, Kupfer T, Radacki K, Wagner K., J. Am. Chem. Soc. 133(47), 2011
PMID: 22032808

Bezier, Adv. Synth. Catal. 355(), 2013

Bezier, Adv. Synth. Catal. 354(), 2012
Copper, silver, and gold complexes in hydrosilylation reactions.
Diez-Gonzalez S, Nolan SP., Acc. Chem. Res. 41(2), 2008
PMID: 18281951

Fasulo, Chem. Sci. 4(), 2013
Silane-isocyanide coupling involving 1,1-insertion of XylNC into the Si-H bond of a σ-silane ligand.
Lipke MC, Tilley TD., J. Am. Chem. Soc. 135(28), 2013
PMID: 23834657
Group 14 hydrides with low valent elements for activation of small molecules.
Mandal SK, Roesky HW., Acc. Chem. Res. 45(2), 2011
PMID: 21882810
Group 14 inorganic hydrocarbon analogues.
Rivard E., Chem Soc Rev 45(4), 2015
PMID: 26219249

Jutzi, Chem. Ber. 109(), 1976
Stabilization of low valent silicon fluorides in the coordination sphere of transition metals.
Azhakar R, Ghadwal RS, Roesky HW, Wolf H, Stalke D., J. Am. Chem. Soc. 134(4), 2012
PMID: 22191508
Donor-acceptor stabilized silaformyl chloride.
Ghadwal RS, Azhakar R, Roesky HW, Propper K, Dittrich B, Goedecke C, Frenking G., Chem. Commun. (Camb.) 48(66), 2012
PMID: 22786582
Donor-acceptor-stabilized silicon analogue of an acid anhydride.
Ghadwal RS, Azhakar R, Roesky HW, Propper K, Dittrich B, Klein S, Frenking G., J. Am. Chem. Soc. 133(44), 2011
PMID: 21999232
Germacarboxylic acid: an organic-acid analogue based on a heavier group 14 element.
Pineda LW, Jancik V, Roesky HW, Herbst-Irmer R., Angew. Chem. Int. Ed. Engl. 43(41), 2004
PMID: 15484239
Lewis base stabilized dichlorosilylene.
Ghadwal RS, Roesky HW, Merkel S, Henn J, Stalke D., Angew. Chem. Int. Ed. Engl. 48(31), 2009
PMID: 19551793
Facile access to silyl-functionalized N-heterocyclic olefins with HSiCl3.
Ghadwal RS, Reichmann SO, Engelhardt F, Andrada DM, Frenking G., Chem. Commun. (Camb.) 49(82), 2013
PMID: 24005446

Sen, Chem. Sci. 3(), 2012
Nucleophilic reactivities of deoxy Breslow intermediates: how does aromaticity affect the catalytic activities of N-heterocyclic carbenes?
Maji B, Horn M, Mayr H., Angew. Chem. Int. Ed. Engl. 51(25), 2012
PMID: 22573542
Structures and reactivities of O-methylated Breslow intermediates.
Maji B, Mayr H., Angew. Chem. Int. Ed. Engl. 51(41), 2012
PMID: 22968992
Carbon dioxide in biomass processing: contributions to the green biorefinery concept.
Morais AR, da Costa Lopes AM, Bogel-Lukasik R., Chem. Rev. 115(1), 2014
PMID: 25411759
Materials chemistry: cooperative carbon capture.
Cooper AI., Nature 519(7543), 2015
PMID: 25762147
Trapping atmospheric CO2 with gold.
Collado A, Gomez-Suarez A, Webb PB, Kruger H, Buhl M, Cordes DB, Slawin AM, Nolan SP., Chem. Commun. (Camb.) 50(77), 2014
PMID: 25116899
CO2 fixation employing an iridium(I)-hydroxide complex.
Truscott BJ, Nelson DJ, Slawin AM, Nolan SP., Chem. Commun. (Camb.) 50(3), 2013
PMID: 24132036
Frustrated Lewis pairs: from concept to catalysis.
Stephan DW., Acc. Chem. Res. 48(2), 2014
PMID: 25535796
Metal-free dehydrogenation of formic acid to H2 and CO2 using boron-based catalysts.
Chauvier C, Tlili A, Das Neves Gomes C, Thuery P, Cantat T., Chem Sci 6(5), 2015
PMID: 29308170
Microfluidic studies of CO2 sequestration by frustrated Lewis pairs.
Voicu D, Abolhasani M, Choueiri R, Lestari G, Seiler C, Menard G, Greener J, Guenther A, Stephan DW, Kumacheva E., J. Am. Chem. Soc. 136(10), 2014
PMID: 24555752
Fast CO2 sequestration, activation, and catalytic transformation using N-heterocyclic olefins.
Wang YB, Wang YM, Zhang WZ, Lu XB., J. Am. Chem. Soc. 135(32), 2013
PMID: 23865980

Jia, Macromolecules 47(), 2014

Tolman, Chem. Rev. 77(), 1977
The Tolman electronic parameter (TEP) and the metal-metal electronic communication in ditopic NHC complexes.
Gusev DG, Peris E., Dalton Trans 42(20), 2013
PMID: 23361446
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

Verlinden, Eur. J. Inorg. Chem. 2015(), 2015

Liske, Organometallics 32(), 2013

Nasr, Coord. Chem. Rev. 316(), 2016

Waters, Coord. Chem. Rev. 293–294(), 2015
Anionic N-heterocyclic carbenes that contain a weakly coordinating borate moiety.
Kronig S, Theuergarten E, Daniliuc CG, Jones PG, Tamm M., Angew. Chem. Int. Ed. Engl. 51(13), 2012
PMID: 22337636
Alkali-Metal-Mediated Magnesiations of an N-Heterocyclic Carbene: Normal, Abnormal, and "Paranormal" Reactivity in a Single Tritopic Molecule.
Martinez-Martinez AJ, Fuentes MA, Hernan-Gomez A, Hevia E, Kennedy AR, Mulvey RE, O'Hara CT., Angew. Chem. Int. Ed. Engl. 54(47), 2015
PMID: 26417985

Armstrong, Chem. Sci. 4(), 2013
Alkali metal salts of ditopic carbanionic carbenes as reagents for the synthesis of novel complexes of group 12 and 14 metals.
Waters JB, Goicoechea JM., Dalton Trans 43(38), 2014
PMID: 24827736
Iron(II) complexes of ditopic carbanionic carbenes.
Musgrave RA, Turbervill RS, Irwin M, Herchel R, Goicoechea JM., Dalton Trans 43(11), 2014
PMID: 24185197

Turbervill, Aust. J. Chem. 66(), 2013
Transition metal complexes of anionic N-heterocyclic dicarbene ligands.
Musgrave RA, Turbervill RS, Irwin M, Goicoechea JM., Angew. Chem. Int. Ed. Engl. 51(43), 2012
PMID: 22961845
Avant-garde metalating agents: structural basis of alkali-metal-mediated metalation.
Mulvey RE., Acc. Chem. Res. 42(6), 2009
PMID: 19348412
NHC-stabilized triorganozincates: syntheses, structures, and transformation to abnormal carbene-zinc complexes.
Wang Y, Xie Y, Abraham MY, Gilliard RJ Jr, Wei P, Campana CF, Schaefer HF 3rd, Schleyer Pv, Robinson GH., Angew. Chem. Int. Ed. Engl. 51(40), 2012
PMID: 22962055

Wang, Organometallics 31(), 2012

Wang, Organometallics 30(), 2011
Iridium(I) complexes with anionic N-heterocyclic carbene ligands as catalysts for the hydrogenation of alkenes in nonpolar media.
Kolychev EL, Kronig S, Brandhorst K, Freytag M, Jones PG, Tamm M., J. Am. Chem. Soc. 135(33), 2013
PMID: 23883399
Site specific carboxylation of abnormal anionic N-heterocyclic dicarbenes with CO2.
Vogt M, Wu C, Oliver AG, Meyer CJ, Schneider WF, Ashfeld BL., Chem. Commun. (Camb.) 49(98), 2013
PMID: 24177269
Synthesis and structural investigation of R2Si (R = Me, Ph) bridged di-N-heterocyclic carbenes.
Ghadwal RS, Reichmann SO, Carl E, Herbst-Irmer R., Dalton Trans 43(36), 2014
PMID: 25101953
Abnormal carbene-silicon halide complexes.
Wang Y, Xie Y, Wei P, Schaefer HF 3rd, Robinson GH., Dalton Trans 45(14), 2015
PMID: 26605692
Stabilization of heterodiatomic SiC through ligand donation: theoretical investigation of SiC(L)2 (L=NHC(Me) , CAAC(Me) , PMe3 ).
Andrada DM, Frenking G., Angew. Chem. Int. Ed. Engl. 54(42), 2015
PMID: 26193457

Cahiez, Adv. Synth. Catal. 357(), 2015
Negishi cross-coupling of secondary alkylzinc halides with aryl/heteroaryl halides using Pd-PEPPSI-IPent.
Calimsiz S, Organ MG., Chem. Commun. (Camb.) 47(18), 2011
PMID: 21286604
Pd-PEPPSI-IPent(Cl): a highly effective catalyst for the selective cross-coupling of secondary organozinc reagents.
Pompeo M, Froese RD, Hadei N, Organ MG., Angew. Chem. Int. Ed. Engl. 51(45), 2012
PMID: 23038603
New in situ trapping metalations of functionalized arenes and heteroarenes with TMPLi in the presence of ZnCl2 and other metal salts.
Frischmuth A, Fernandez M, Barl NM, Achrainer F, Zipse H, Berionni G, Mayr H, Karaghiosoff K, Knochel P., Angew. Chem. Int. Ed. Engl. 53(30), 2014
PMID: 24923789
Continuous flow magnesiation of functionalized heterocycles and acrylates with TMPMgCl⋅LiCl.
Petersen TP, Becker MR, Knochel P., Angew. Chem. Int. Ed. Engl. 53(30), 2014
PMID: 24962240

Winkler, Organometallics 35(), 2016

Igarashi, Organometallics 35(), 2016
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 27427200
PubMed | Europe PMC

Suchen in

Google Scholar