Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids
Boettcher T, Steinhauer S, Allefeld N, Hoge B, Neumann B, Stammler H-G, Bassil BS, Winter M, Mitzel NW, Roeschenthaler G-V (2014)
Dalton Transactions 43(7): 2979-2987.
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Autor*in
Boettcher, Tobias;
Steinhauer, SimonUniBi;
Allefeld, NadineUniBi;
Hoge, BertholdUniBi;
Neumann, BeateUniBi;
Stammler, Hans-GeorgUniBi;
Bassil, Bassem S.;
Winter, Martin;
Mitzel, Norbert W.UniBi;
Roeschenthaler, Gerd-Volker
Abstract / Bemerkung
The crystal structures of the previously reported 2,2-difluoro-1,3-dimethylimidazolidine and its acyclic analog were determined by in situ crystallization. Both liquid fluorinating agents have recently been introduced as potent precursors for the synthesis of p-block element carbene complexes. These fluorine compounds were compared with chloro-amidinium chlorides, which are already established carbene precursors. The chlorides were characterized as ion pairs and contrasted to the previous interpretation as charge-transfer complexes between carbene and dichlorine. Furthermore, the two precursors are used for the synthesis of a series of new carbene complexes of phosphorus( V) fluorides substituted with perfluoroalkyl-groups. These unusually stable hexacoordinate phosphorus( V) complexes were treated with anhydrous hydrogen fluoride to yield imidazolium phosphates. This procedure allows the synthesis of salts used as ionic liquids in high yield and high purity.
Erscheinungsjahr
2014
Zeitschriftentitel
Dalton Transactions
Band
43
Ausgabe
7
Seite(n)
2979-2987
ISSN
1477-9226
eISSN
1477-9234
Page URI
https://pub.uni-bielefeld.de/record/2660903
Zitieren
Boettcher T, Steinhauer S, Allefeld N, et al. Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions. 2014;43(7):2979-2987.
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H. - G., Bassil, B. S., et al. (2014). Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions, 43(7), 2979-2987. doi:10.1039/c3dt53043d
Boettcher, Tobias, Steinhauer, Simon, Allefeld, Nadine, Hoge, Berthold, Neumann, Beate, Stammler, Hans-Georg, Bassil, Bassem S., Winter, Martin, Mitzel, Norbert W., and Roeschenthaler, Gerd-Volker. 2014. “Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids”. Dalton Transactions 43 (7): 2979-2987.
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H. - G., Bassil, B. S., Winter, M., Mitzel, N. W., and Roeschenthaler, G. - V. (2014). Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions 43, 2979-2987.
Boettcher, T., et al., 2014. Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions, 43(7), p 2979-2987.
T. Boettcher, et al., “Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids”, Dalton Transactions, vol. 43, 2014, pp. 2979-2987.
Boettcher, T., Steinhauer, S., Allefeld, N., Hoge, B., Neumann, B., Stammler, H.-G., Bassil, B.S., Winter, M., Mitzel, N.W., Roeschenthaler, G.-V.: Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids. Dalton Transactions. 43, 2979-2987 (2014).
Boettcher, Tobias, Steinhauer, Simon, Allefeld, Nadine, Hoge, Berthold, Neumann, Beate, Stammler, Hans-Georg, Bassil, Bassem S., Winter, Martin, Mitzel, Norbert W., and Roeschenthaler, Gerd-Volker. “Carbene complexes of phosphorus(V) fluorides substituted with perfluoroalkyl-groups synthesized by oxidative addition. Cleavage of the complexes reveals a new synthetic protocol for ionic liquids”. Dalton Transactions 43.7 (2014): 2979-2987.
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Sonnenberg K, Pröhm P, Müller C, Beckers H, Steinhauer S, Lentz D, Riedel S., Chemistry 24(5), 2018
PMID: 29244220
Sonnenberg K, Pröhm P, Müller C, Beckers H, Steinhauer S, Lentz D, Riedel S., Chemistry 24(5), 2018
PMID: 29244220
Small molecule activation: SbF3 auto-ionization supported by transfer and mesoionic NHC rearrangement.
Alič B, Štefančič A, Tavčar G., Dalton Trans 46(10), 2017
PMID: 28230220
Alič B, Štefančič A, Tavčar G., Dalton Trans 46(10), 2017
PMID: 28230220
Crystal structure of 2-chloro-1,3-(2,6-diiso-propyl-phen-yl)-4,5-dihydro-1H-imidazol-3-ium tetra-kis-(3,5-tri-fluoro-methyl-phen-yl)borate.
Stack DL, Masuda JD., Acta Crystallogr E Crystallogr Commun 72(pt 10), 2016
PMID: 27746944
Stack DL, Masuda JD., Acta Crystallogr E Crystallogr Commun 72(pt 10), 2016
PMID: 27746944
55 References
Daten bereitgestellt von Europe PubMed Central.
Arduengo, J. Am. Chem. Soc. 113(), 1991
Arduengo, Acc. Chem. Res. 32(), 1999
Herrmann, Angew. Chem., Int. Ed. Engl. 36(), 1997
Hahn, Angew. Chem., Int. Ed. 47(), 2008
Crudden, Coord. Chem. Rev. 248(), 2004
Droge, Angew. Chem., Int. Ed. 49(), 2010
Herrmann, Angew. Chem., Int. Ed. Engl. 34(), 1995
Herrmann, Angew. Chem., Int. Ed. 41(), 2002
N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union.
Fortman GC, Nolan SP., Chem Soc Rev 40(10), 2011
PMID: 21731956
Fortman GC, Nolan SP., Chem Soc Rev 40(10), 2011
PMID: 21731956
Complexes with poly(N-heterocyclic carbene) ligands: structural features and catalytic applications.
Poyatos M, Mata JA, Peris E., Chem. Rev. 109(8), 2009
PMID: 19236010
Poyatos M, Mata JA, Peris E., Chem. Rev. 109(8), 2009
PMID: 19236010
Cazin, 2011
Nolan, 2006
N-heterocyclic carbenes in late transition metal catalysis.
Diez-Gonzalez S, Marion N, Nolan SP., Chem. Rev. 109(8), 2009
PMID: 19588961
Diez-Gonzalez S, Marion N, Nolan SP., Chem. Rev. 109(8), 2009
PMID: 19588961
Marion, Angew. Chem. 119(), 2007
Marion, Angew. Chem., Int. Ed. 46(), 2007
de, Coord. Chem. Rev. 253(), 2009
Glorius, 2007
Arduengo, Tetrahedron 55(), 1999
Peris, 2007
Kuhn, Coord. Chem. Rev. 249(), 2005
Kirmse, Eur. J. Org. Chem. (), 2005
Chemistry. Soluble allotropes of main-group elements.
Dyker CA, Bertrand G., Science 321(5892), 2008
PMID: 18719272
Dyker CA, Bertrand G., Science 321(5892), 2008
PMID: 18719272
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
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, von R Schleyer P, Robinson GH., Science 321(5892), 2008
PMID: 18719279
Sidiropoulos, Angew. Chem., Int. Ed. 48(), 2009
An N-heterocyclic carbene adduct of diatomic tin, :Sn=Sn:.
Jones C, Sidiropoulos A, Holzmann N, Frenking G, Stasch A., Chem. Commun. (Camb.) 48(79), 2012
PMID: 22933046
Jones C, Sidiropoulos A, Holzmann N, Frenking G, Stasch A., Chem. Commun. (Camb.) 48(79), 2012
PMID: 22933046
Carbene-stabilized diphosphorus.
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, Schleyer Pv, Robinson GH., J. Am. Chem. Soc. 130(45), 2008
PMID: 18937460
Wang Y, Xie Y, Wei P, King RB, Schaefer HF 3rd, Schleyer Pv, Robinson GH., J. Am. Chem. Soc. 130(45), 2008
PMID: 18937460
Abraham, Chem.–Eur. J. 16(), 2010
Ambient-temperature isolation of a compound with a boron-boron triple bond.
Braunschweig H, Dewhurst RD, Hammond K, Mies J, Radacki K, Vargas A., Science 336(6087), 2012
PMID: 22700924
Braunschweig H, Dewhurst RD, Hammond K, Mies J, Radacki K, Vargas A., Science 336(6087), 2012
PMID: 22700924
Carbene stabilization of highly reactive main-group molecules.
Wang Y, Robinson GH., Inorg Chem 50(24), 2011
PMID: 21634365
Wang Y, Robinson GH., Inorg Chem 50(24), 2011
PMID: 21634365
Carbene-stabilized main group diatomic allotropes.
Wang Y, Robinson GH., Dalton Trans 41(2), 2011
PMID: 21904737
Wang Y, Robinson GH., Dalton Trans 41(2), 2011
PMID: 21904737
Complexes of Ge(IV)- and Sn(IV)-fluorides with cyclic and acyclic carbenes: bis(dialkylamino)-difluoromethylenes as carbene sources.
Bottcher T, Bassil BS, Roschenthaler GV., Inorg Chem 51(2), 2012
PMID: 22216889
Bottcher T, Bassil BS, Roschenthaler GV., Inorg Chem 51(2), 2012
PMID: 22216889
Böttcher, Organometallics 31(), 2012
Böttcher, Chem. Sci. 4(), 2013
Denk, Angew. Chem., Int. Ed. Engl. 36(), 1997
Alder, Angew. Chem., Int. Ed. Engl. 35(), 1996
Dippel, J. Electrochem. Soc. 159(), 2012
Pajkert, Tetrahedron 69(), 2013
Hayashi, Chem. Commun. (), 2002
Fürstner, Organometallics 22(), 2003
Kremzow, Chem.–Eur. J. 11(), 2005
Fink, J. Chem. Phys. 71(), 1979
Ghosh, J. Chem. Phys. 20(), 1952
Cole, New J. Chem. 26(), 2002
Kuhn, Z. Anorg. Allg. Chem. 628(), 2002
Tiritiris, Z. Kristallogr. 223(), 2008
Fujisawa, Chem. Lett. (), 1982
Petrov, Zh. Strukt. Khim. (), 1985
Petrov, J. Struct. Chem. 26(), 1985
Herzberg, 1950
Shibata, J. Phys. Chem. 67(), 1963
Donohue, Acta Crystallogr., Sect. A: Found. Crystallogr. 18(), 1965
Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr. 64(), 2008
Kolomeitsev, J. Fluorine Chem. 103(), 2000
Isobe, J. Org. Chem. 64(), 1999
Zakharov, 0
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