The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity

Jutzi P (2014)
Chemistry - A European Journal 20(30): 9192-9207.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
In the flourishing chemistry of divalent silicon, pi-complex formation between silicon and the pentamethylcyclopentadienyl (Cp*) group is one of the successful strategies for thermodynamic and/or kinetic stabilization. Here, the diverse reactivity of the [Cp*Si](+) ion is described. Its chemistry is characterized by the addition of anionic and neutral nucleophiles and by the easy hapticity change and the leaving-group character of the Cp* group. Several novel sandwich and half-sandwich pi-complexes of divalent silicon were synthesized, and a novel access to the class of cyclotrisilenes was found. A reversible adduct formation is the basis for the catalytic activity of the [Cp*Si](+) ion in the specific oligoether degradation. Homo-or heterolytic Cp*-Si bond cleavage allows the use of the cation as a source of silicon atoms in silicon cluster synthesis and in nanoparticle formation.
Stichworte
catalysis; cyclopentadienyl ligands; silicon; silicon(II) cation; pi interactions; nucleophilic addition
Erscheinungsjahr
2014
Zeitschriftentitel
Chemistry - A European Journal
Band
20
Ausgabe
30
Seite(n)
9192-9207
ISSN
0947-6539
Page URI
https://pub.uni-bielefeld.de/record/2695036

Zitieren

Jutzi P. The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal. 2014;20(30):9192-9207.
Jutzi, P. (2014). The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal, 20(30), 9192-9207. doi:10.1002/chem.201402163
Jutzi, Peter. 2014. “The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity”. Chemistry - A European Journal 20 (30): 9192-9207.
Jutzi, P. (2014). The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal 20, 9192-9207.
Jutzi, P., 2014. The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal, 20(30), p 9192-9207.
P. Jutzi, “The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity”, Chemistry - A European Journal, vol. 20, 2014, pp. 9192-9207.
Jutzi, P.: The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity. Chemistry - A European Journal. 20, 9192-9207 (2014).
Jutzi, Peter. “The Pentamethylcyclopentadienylsilicon(II) Cation: Synthesis, Characterization, and Reactivity”. Chemistry - A European Journal 20.30 (2014): 9192-9207.

4 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Atomically Precise Expansion of Unsaturated Silicon Clusters.
Leszczyńska KI, Huch V, Präsang C, Schwabedissen J, Berger RJF, Scheschkewitz D., Angew Chem Int Ed Engl 58(15), 2019
PMID: 30633856
Taming the Cationic Beast: Novel Developments in the Synthesis and Application of Weakly Coordinating Anions.
Riddlestone IM, Kraft A, Schaefer J, Krossing I., Angew Chem Int Ed Engl 57(43), 2018
PMID: 29266644
Chalcogen-atom transfer and exchange reactions of NHC-stabilized heavier silaacylium ions.
Sarkar D, Wendel D, Ahmad SU, Szilvási T, Pöthig A, Inoue S., Dalton Trans 46(46), 2017
PMID: 29120473

166 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0

Gaspar, 1981

Tang, 1982

Atwell, Angew. Chem. 81(), 1969

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 8(), 1969

AUTHOR UNKNOWN, 0

Weidenbruch, Coord. Chem. Rev. 130(), 1994

Douglas, Can. J. Phys. 48(), 1970

Sumiyoshi, Chem. Phys. Lett. 214(), 1993

Singh, Astron. Astrophys. 9(), 1978

Kira, J. Am. Chem. Soc. 121(), 1999
New isolable dialkylsilylene and its isolable dimer that equilibrate in solution.
Abe T, Tanaka R, Ishida S, Kira M, Iwamoto T., J. Am. Chem. Soc. 134(49), 2012
PMID: 23171322

Denk, J. Am. Chem. Soc. 116(), 1994

Gehrhus, J. Chem. Soc. Chem. Commun. (), 1995
A new type of N-heterocyclic silylene with ambivalent reactivity.
Driess M, Yao S, Brym M, van Wullen C, Lentz D., J. Am. Chem. Soc. 128(30), 2006
PMID: 16866506

Asay, Angew. Chem. 123(), 2011
Aromatic ylide-stabilized carbocyclic silylene.
Asay M, Inoue S, Driess M., Angew. Chem. Int. Ed. Engl. 50(41), 2011
PMID: 21882326

Ghadwal, Angew. Chem. 123(), 2011
A dimer of silaisonitrile with two-coordinate silicon atoms.
Ghadwal RS, Roesky HW, Propper K, Dittrich B, Klein S, Frenking G., Angew. Chem. Int. Ed. Engl. 50(23), 2011
PMID: 21574229

AUTHOR UNKNOWN, 0

Jutzi, Angew. Chem. 98(), 1986

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 25(), 1986

Jutzi, Chem. Ber. 122(), 1989
The (Me5C5)Si+ cation: a stable derivative of HSi+.
Jutzi P, Mix A, Rummel B, Schoeller WW, Neumann B, Stammler HG., Science 305(5685), 2004
PMID: 15232074
Isolation of a stable, acyclic, two-coordinate silylene.
Rekken BD, Brown TM, Fettinger JC, Tuononen HM, Power PP., J. Am. Chem. Soc. 134(15), 2012
PMID: 22443813
A stable two-coordinate acyclic silylene.
Protchenko AV, Birjkumar KH, Dange D, Schwarz AD, Vidovic D, Jones C, Kaltsoyannis N, Mountford P, Aldridge S., J. Am. Chem. Soc. 134(15), 2012
PMID: 22443679

AUTHOR UNKNOWN, 0

So, Angew. Chem. 118(), 2006
Synthesis and characterization of [PhC(NtBu)2]SiCl: a stable monomeric chlorosilylene.
So CW, Roesky HW, Magull J, Oswald RB., Angew. Chem. Int. Ed. Engl. 45(24), 2006
PMID: 16671135

Junold, Angew. Chem. 124(), 2012

Yao, Angew. Chem. 119(), 2007

Driess, Angew. Chem. 118(), 2006
Low-valent silicon cations with two-coordinate silicon and aromatic character.
Driess M, Yao S, Brym M, van Wullen C., Angew. Chem. Int. Ed. Engl. 45(40), 2006
PMID: 16986190
Stable phosphonium sila-ylide with reactivity as a sila-Wittig reagent.
Gau D, Kato T, Saffon-Merceron N, Cossio FP, Baceiredo A., J. Am. Chem. Soc. 131(25), 2009
PMID: 19496597

Karsch, Angew. Chem. 102(), 1990

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 29(), 1990

Ghadwal, Angew. Chem. 121(), 2009
Lewis base stabilized dichlorosilylene.
Ghadwal RS, Roesky HW, Merkel S, Henn J, Stalke D., Angew. Chem. Int. Ed. Engl. 48(31), 2009
PMID: 19551793

Mondal, Angew. Chem. 125(), 2013
Conversion of a singlet silylene to a stable biradical.
Mondal KC, Roesky HW, Schwarzer MC, Frenking G, Tkach I, Wolf H, Kratzert D, Herbst-Irmer R, Niepotter B, Stalke D., Angew. Chem. Int. Ed. Engl. 52(6), 2012
PMID: 23280727

Filippou, Angew. Chem. 121(), 2009
SiBr2(Idipp): a stable N-heterocyclic carbene adduct of dibromosilylene.
Filippou AC, Chernov O, Schnakenburg G., Angew. Chem. Int. Ed. Engl. 48(31), 2009
PMID: 19569161

Filippou, Angew. Chem. 125(), 2013
Silicon(II) coordination chemistry: N-heterocyclic carbene complexes of Si2+ and SiI+.
Filippou AC, Lebedev YN, Chernov O, Straßmann M, Schnakenburg G., Angew. Chem. Int. Ed. Engl. 52(27), 2013
PMID: 23712776
Room-temperature dissociation of 1,2-dibromodisilenes to bromosilylenes.
Suzuki K, Matsuo T, Hashizume D, Tamao K., J. Am. Chem. Soc. 133(49), 2011
PMID: 22074252

Xiong, Angew. Chem. 125(), 2013
A cyclic silylone ("siladicarbene") with an electron-rich silicon(0) atom.
Xiong Y, Yao S, Inoue S, Epping JD, Driess M., Angew. Chem. Int. Ed. Engl. 52(28), 2013
PMID: 23729354

Xiong, Angew. Chem. 124(), 2012
The elusive silyliumylidene [ClSi:]+ and silathionium [ClSi=S]+ cations stabilized by bis(iminophosphorane) chelate ligand.
Xiong Y, Yao S, Inoue S, Irran E, Driess M., Angew. Chem. Int. Ed. Engl. 51(40), 2012
PMID: 22965539

Kühler, Adv. Organomet. Chem. 49(), 2003
Stable silylenes.
Haaf M, Schmedake TA, West R., Acc. Chem. Res. 33(10), 2000
PMID: 11041835

Gehrhus, J. Organomet. Chem. 617-618(), 2001

Kira, J. Chem. Sci. 124(), 2012
Stable heavier carbene analogues.
Mizuhata Y, Sasamori T, Tokitoh N., Chem. Rev. 109(8), 2009
PMID: 19630390

Yao, Organometallics 30(), 2011

AUTHOR UNKNOWN, 0

Sen, Chem. Sci. 3(), 2012
A silyliumylidene cation stabilized by an amidinate ligand and 4-dimethylaminopyridine.
Yeong HX, Xi HW, Li Y, Lim KH, So CW., Chemistry 19(35), 2013
PMID: 23853083

AUTHOR UNKNOWN, 0

Kira, Adv. Organomet. Chem. 54(), 2006
Synthetic development and chemical reactivity of transition-metal silylene complexes.
Waterman R, Hayes PG, Tilley TD., Acc. Chem. Res. 40(8), 2007
PMID: 17477497

AUTHOR UNKNOWN, 0

Asay, Bull. Chem. Soc. Jpn. 85(), 2012

AUTHOR UNKNOWN, 0

Sen, Angew. Chem. 121(), 2009
A remarkable base-stabilized bis(silylene) with a silicon(I)-silicon(I) bond.
Sen SS, Jana A, Roesky HW, Schulzke C., Angew. Chem. Int. Ed. Engl. 48(45), 2009
PMID: 19802861

Gau, Angew. Chem. 123(), 2011
Synthesis of a stable disilyne bisphosphine adduct and its non-metal-mediated CO2 reduction to CO.
Gau D, Rodriguez R, Kato T, Saffon-Merceron N, de Cozar A, Cossio FP, Baceiredo A., Angew. Chem. Int. Ed. Engl. 50(5), 2010
PMID: 21268202
A planar rhombic charge-separated tetrasilacyclobutadiene.
Suzuki K, Matsuo T, Hashizume D, Fueno H, Tanaka K, Tamao K., Science 331(6022), 2011
PMID: 21393541
A stable silicon(0) compound with a Si=Si double bond.
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, von R Schleyer P, Robinson GH., Science 321(5892), 2008
PMID: 18719279

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Mondal, Angew. Chem. 125(), 2013
A stable singlet biradicaloid siladicarbene: (L:)2Si.
Mondal KC, Roesky HW, Schwarzer MC, Frenking G, Niepotter B, Wolf H, Herbst-Irmer R, Stalke D., Angew. Chem. Int. Ed. Engl. 52(10), 2013
PMID: 23307744

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
A tricyclic aromatic isomer of hexasilabenzene.
Abersfelder K, White AJ, Rzepa HS, Scheschkewitz D., Science 327(5965), 2010
PMID: 20110501

Jutzi, J. Organomet. Chem. 446(), 1993

Jutzi, Angew. Chem. 104(), 1992

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 31(), 1992

Jutzi, J. Chem. Soc. Chem. Commun. (), 1988

Jutzi, Organometallics 19(), 2000

Mix, Organometallics 29(), 2010

Krossing, Angew. Chem. 116(), 2004
Noncoordinating anions--fact or fiction? A survey of likely candidates.
Krossing I, Raabe I., Angew. Chem. Int. Ed. Engl. 43(16), 2004
PMID: 15083452

Reed, Acc. Chem. Res. 31(), 1998

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Jutzi, Chem. Ber. 121(), 1988

AUTHOR UNKNOWN, 0

Berger, Silicon 2(), 2010

Jemmis, J. Am. Chem. Soc. 104(), 1982

Macdonald, J. Am. Chem. Soc. 121(), 1999

Jutzi, J. Chem. Soc. Dalton Trans. (), 2000

Pichierri, Chem. Phys. Lett. 568-569(), 2013

AUTHOR UNKNOWN, 0

Wade, Adv. Inorg. Radiochem. 18(), 1976

Williams, Adv. Inorg. Radiochem. 18(), 1976

Rudolph, Acc. Chem. Res. 9(), 1976

Sitzmann, Z. Naturforsch. B 52(), 1997
Novel pi-complexes of divalent silicon: mixed substituted neutral sandwich compounds and the half-sandwich cation (iPr5C5)Si+.
Jutzi P, Mix A, Neumann B, Rummel B, Stammler HG., Chem. Commun. (Camb.) (33), 2006
PMID: 16921431

Jutzi, Chem. Ber. 122(), 1989

Jutzi, J. Organomet. Chem. 552(), 1998

Peng, Chem. Sci. 1(), 2010
Main-group elements as transition metals.
Power PP., Nature 463(7278), 2010
PMID: 20075912

Puranik, J. Am. Chem. Soc. 111(), 1989

Tokitoh, J. Am. Chem. Soc. 115(), 1993

Schiemenz, Organometallics 15(), 1996

Jutzi, Angew. Chem. 121(), 2009
[2,6-(Trip)2H3C6](Cp*)Si: a stable monomeric arylsilicon(II) compound.
Jutzi P, Leszczynska K, Neumann B, Schoeller WW, Stammler HG., Angew. Chem. Int. Ed. Engl. 48(14), 2009
PMID: 19248074

Gynane, J. Chem. Soc. Dalton Trans. (), 1977

Jutzi, Organometallics 5(), 1986
One pot synthesis of disilatricycloheptene analogue and Jutzi's disilene.
Khan S, Sen SS, Roesky HW, Kratzert D, Michel R, Stalke D., Inorg Chem 49(20), 2010
PMID: 20839843

Zhang, Organometallics 30(), 2011

Beer, Organometallics 28(), 2009

Inoue, Angew. Chem. 124(), 2012

Jutzi, Organometallics 29(), 2010

AUTHOR UNKNOWN, 0

Simons, J. Am. Chem. Soc. 118(), 1996

Malisch, J. Organomet. Chem. 507(), 1996

Huttner, Acc. Chem. Res. 19(), 1986

Stender, J. Chem. Soc. Dalton Trans. (), 2001

Jutzi, Organometallics 28(), 2009

Kwon, 2001

Budzelaar, Organometallics 22(), 2003
Hapticity uncovered: real-space bonding indicators for zincocene chemistry.
Mebs S, Chilleck MA, Grabowsky S, Braun T., Chemistry 18(37), 2012
PMID: 22893522

Huttner, J. Organomet. Chem. 145(), 1978

Jordan, Eur. J. Inorg. Chem. (), 2007

Elschenbroich, 2003

Leszczyńska, Angew. Chem. 124(), 2012
Reversible base coordination to a disilene.
Leszczynska K, Abersfelder K, Mix A, Neumann B, Stammler HG, Cowley MJ, Jutzi P, Scheschkewitz D., Angew. Chem. Int. Ed. Engl. 51(27), 2012
PMID: 22639373

Glasovac, Theor. Chem. 124(), 2009
An N-heterocyclic carbene-disilyne complex and its reactivity toward ZnCl2.
Yamaguchi T, Sekiguchi A, Driess M., J. Am. Chem. Soc. 132(40), 2010
PMID: 20843081
Equilibrium between a cyclotrisilene and an isolable base adduct of a disilenyl silylene.
Cowley MJ, Huch V, Rzepa HS, Scheschkewitz D., Nat Chem 5(10), 2013
PMID: 24056345

AUTHOR UNKNOWN, 0

Leszczyńska, Angew. Chem. 123(), 2011
The pentamethylcyclopentadienylsilicon(II) cation as a catalyst for the specific degradation of oligo(ethyleneglycol) diethers.
Leszczynska K, Mix A, Berger RJ, Rummel B, Neumann B, Stammler HG, Jutzi P., Angew. Chem. Int. Ed. Engl. 50(30), 2011
PMID: 21656879
A cryptand-encapsulated germanium(II) dication.
Rupar PA, Staroverov VN, Baines KM., Science 322(5906), 2008
PMID: 19039131

Rupar, Angew. Chem. 121(), 2009
Cationic crown ether complexes of germanium(II).
Rupar PA, Bandyopadhyay R, Cooper BF, Stinchcombe MR, Ragogna PJ, Macdonald CL, Baines KM., Angew. Chem. Int. Ed. Engl. 48(28), 2009
PMID: 19479914

Bandyopadhyay, Angew. Chem. 125(), 2013
Water and ammonia complexes of germanium(II) dications.
Bandyopadhyay R, Nguyen JH, Swidan A, Macdonald CL., Angew. Chem. Int. Ed. Engl. 52(12), 2013
PMID: 23404851
Cationic cryptand complexes of tin(II).
Avery JC, Hanson MA, Herber RH, Bladek KJ, Rupar PA, Nowik I, Huang Y, Baines KM., Inorg Chem 51(13), 2012
PMID: 22686452

AUTHOR UNKNOWN, 0

Jutzi, Silicon Chem. 3(), 2007

Jutzi, Angew. Chem. 112(), 2000
Stable Systems with a Triple Bond to Silicon or Its Homologues: Another Challenge.
Jutzi P., Angew. Chem. Int. Ed. Engl. 39(21), 2000
PMID: 29711715

AUTHOR UNKNOWN, 0

Jutzi, Pure Appl. Chem. 75(), 2003
The Cp*Si+ cation as a stoichiometric source of silicon.
Leszczynska K, Abersfelder K, Majumdar M, Neumann B, Stammler HG, Rzepa HS, Jutzi P, Scheschkewitz D., Chem. Commun. (Camb.) 48(63), 2012
PMID: 22760501

Krossing, Eur. J. Inorg. Chem. (), 2005
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