Sodium Phosphaethynolate as a Building Block for Heterocycles

Chen X, Alidori S, Puschmann FF, Santiso-Quinones G, Benko Z, Li Z, Becker G, Grützmacher H-F, Gruetzmacher H (2014)
Angewandte Chemie International Edition 53(6): 1641-1645.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Autor*in
Chen, Xiaodan; Alidori, Simone; Puschmann, Florian Frank; Santiso-Quinones, Gustavo; Benko, Zoltan; Li, Zhongshu; Becker, Gerd; Grützmacher, Hans-FriedrichUniBi; Gruetzmacher, Hansjoerg
Abstract / Bemerkung
Phosphorus-containing heterocycles have evolved from laboratory curiosities to functional components, such as ligands in catalytically active metal complexes or molecular constituents in electronic devices. The straightforward synthesis of functionalized heterocycles on a larger scale remains a challenge. Herein, we report the use of the phosphaethynolate (OCP)(-) anion as a building block for various sterically unprotected and functionalized hydroxy substituted phosphorus heterocycles. Because the resulting heterocycles are themselves anions, they are building blocks in their own right and allow further facile functionalization. This property may be of interest in coordination chemistry and material science.
Stichworte
phosphorus heterocycles; phosphinines; cycloaddition; multiple bonds; sodium phosphaethynolate
Erscheinungsjahr
2014
Zeitschriftentitel
Angewandte Chemie International Edition
Band
53
Ausgabe
6
Seite(n)
1641-1645
ISSN
1433-7851
Page URI
https://pub.uni-bielefeld.de/record/2664323

Zitieren

Chen X, Alidori S, Puschmann FF, et al. Sodium Phosphaethynolate as a Building Block for Heterocycles. Angewandte Chemie International Edition. 2014;53(6):1641-1645.
Chen, X., Alidori, S., Puschmann, F. F., Santiso-Quinones, G., Benko, Z., Li, Z., Becker, G., et al. (2014). Sodium Phosphaethynolate as a Building Block for Heterocycles. Angewandte Chemie International Edition, 53(6), 1641-1645. doi:10.1002/anie.201308220
Chen, Xiaodan, Alidori, Simone, Puschmann, Florian Frank, Santiso-Quinones, Gustavo, Benko, Zoltan, Li, Zhongshu, Becker, Gerd, Grützmacher, Hans-Friedrich, and Gruetzmacher, Hansjoerg. 2014. “Sodium Phosphaethynolate as a Building Block for Heterocycles”. Angewandte Chemie International Edition 53 (6): 1641-1645.
Chen, X., Alidori, S., Puschmann, F. F., Santiso-Quinones, G., Benko, Z., Li, Z., Becker, G., Grützmacher, H. - F., and Gruetzmacher, H. (2014). Sodium Phosphaethynolate as a Building Block for Heterocycles. Angewandte Chemie International Edition 53, 1641-1645.
Chen, X., et al., 2014. Sodium Phosphaethynolate as a Building Block for Heterocycles. Angewandte Chemie International Edition, 53(6), p 1641-1645.
X. Chen, et al., “Sodium Phosphaethynolate as a Building Block for Heterocycles”, Angewandte Chemie International Edition, vol. 53, 2014, pp. 1641-1645.
Chen, X., Alidori, S., Puschmann, F.F., Santiso-Quinones, G., Benko, Z., Li, Z., Becker, G., Grützmacher, H.-F., Gruetzmacher, H.: Sodium Phosphaethynolate as a Building Block for Heterocycles. Angewandte Chemie International Edition. 53, 1641-1645 (2014).
Chen, Xiaodan, Alidori, Simone, Puschmann, Florian Frank, Santiso-Quinones, Gustavo, Benko, Zoltan, Li, Zhongshu, Becker, Gerd, Grützmacher, Hans-Friedrich, and Gruetzmacher, Hansjoerg. “Sodium Phosphaethynolate as a Building Block for Heterocycles”. Angewandte Chemie International Edition 53.6 (2014): 1641-1645.

26 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Synthesis and Reactivity of Nickel-Stabilised μ2 :η2 ,η2 -P2 , As2 and PAs Units.
Hierlmeier G, Hinz A, Wolf R, Goicoechea JM., Angew Chem Int Ed Engl 57(2), 2018
PMID: 29152826
An isolable magnesium diphosphaethynolate complex.
Gilliard RJ, Heift D, Benkő Z, Keiser JM, Rheingold AL, Grützmacher H, Protasiewicz JD., Dalton Trans 47(3), 2018
PMID: 29242885
An Isolable Phosphaethynolatoborane and Its Reactivity.
Wilson DWN, Hinz A, Goicoechea JM., Angew Chem Int Ed Engl 57(8), 2018
PMID: 29316112
Functional Disilenes in Synthesis.
Rammo A, Scheschkewitz D., Chemistry 24(27), 2018
PMID: 29193341
Simple Synthesis of Functionalized 2-Phosphanaphthalenes.
Mei Y, Wu DJ, Borger JE, Grützmacher H., Angew Chem Int Ed Engl 57(19), 2018
PMID: 29508510
A substituent-tolerant synthetic approach to N/P-"loaded" heteroarenes.
Polezhaev AV, Beagan DM, Cabelof AC, Chen CH, Caulton KG., Dalton Trans 47(17), 2018
PMID: 29658560
Multidentate Phosphanyl Phosphinines: Synthesis and Properties.
Chen X, Li Z, Grützmacher H., Chemistry 24(33), 2018
PMID: 29644747
A General Synthesis of Phosphorus- and Arsenic-Containing Analogues of the Thio- and Seleno-cyanate Anions.
Tambornino F, Hinz A, Köppe R, Goicoechea JM., Angew Chem Int Ed Engl 57(27), 2018
PMID: 29786936
2,4,6-Tri(hydroxy)-1,3,5-triphosphinine, P3 C3 (OH)3 : The Phosphorus Analogue of Cyanuric Acid.
Suter R, Mei Y, Baker M, Benkő Z, Li Z, Grützmacher H., Angew Chem Int Ed Engl 56(5), 2017
PMID: 28026077
Insertion of sodium phosphaethynolate, Na[OCP], into a zirconium-benzyne complex.
Kieser JM, Gilliard RJ, Rheingold AL, Grützmacher H, Protasiewicz JD., Chem Commun (Camb) 53(37), 2017
PMID: 28430281
Annulated 1,3,4-Azadiphospholides: Heterocycles with Widely Tunable Optical Properties.
Suter R, Benkő Z, Bispinghoff M, Grützmacher H., Angew Chem Int Ed Engl 56(37), 2017
PMID: 28714552
Borane-Stabilized Isomeric Dimers of the Phosphaethynolate Anion.
Szkop KM, Jupp AR, Suter R, Grützmacher H, Stephan DW., Angew Chem Int Ed Engl 56(45), 2017
PMID: 28922529
Fifty Years of (Benz)oxaphospholene Chemistry.
Berton JKET, Heugebaert TSA, Virieux D, Stevens CV., Chemistry 23(69), 2017
PMID: 28802072
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 of Au-, Co-η1PCO and Cu-η2PCO complexes, conversion of an Ir-η1PCO complex into a dimetalladiphosphene, and an interaction-free PCO anion.
Liu L, Ruiz DA, Dahcheh F, Bertrand G, Suter R, Tondreau AM, Grützmacher H., Chem Sci 7(3), 2016
PMID: 29997776
From a Phosphaketenyl-Functionalized Germylene to 1,3-Digerma-2,4-diphosphacyclobutadiene.
Yao S, Xiong Y, Szilvási T, Grützmacher H, Driess M., Angew Chem Int Ed Engl 55(15), 2016
PMID: 26938015
N-Heterocyclic carbene phosphaketene adducts as precursors to carbene-phosphinidene adducts and a rearranged π-system.
Li Z, Chen X, Li Y, Su CY, Grützmacher H., Chem Commun (Camb) 52(76), 2016
PMID: 27545980
A Convenient Synthesis of 1,2,4- and 1,3,4-Azadiphospholes.
Suter R, Benkő Z, Grützmacher H., Chemistry 22(42), 2016
PMID: 27576588
Simple access to ionic liquids and organic salts containing the phosphaethynolate (PCO(-)) and Zintl (Sb11(3-)) anions.
Jost M, Finger LH, Sundermeyer J, von Hänisch C., Chem Commun (Camb) 52(78), 2016
PMID: 27602991
6-Methoxy-5-phosphaphenanthrene: a molecule with an unreactive P=C double bond.
Wang L, Wang Z, Wang Q, Duan Z, Mathey F., Dalton Trans 44(8), 2015
PMID: 25619732
Synthesis of phosphabenzenes by an iron-catalyzed [2+2+2] cycloaddition reaction of diynes with phosphaalkynes.
Nakajima K, Takata S, Sakata K, Nishibayashi Y., Angew Chem Int Ed Engl 54(26), 2015
PMID: 25981197
Phosphaketenes as building blocks for the synthesis of triphospha heterocycles.
Heift D, Benkő Z, Grützmacher H., Chemistry 20(36), 2014
PMID: 25055973

45 References

Daten bereitgestellt von Europe PubMed Central.


AUTHOR UNKNOWN, 0
Synthesis and characterization of terminal [Re(XCO)(CO)2(triphos)] (X=N, P): isocyanate versus phosphaethynolate complexes.
Alidori S, Heift D, Santiso-Quinones G, Benko Z, Grutzmacher H, Caporali M, Gonsalvi L, Rossin A, Peruzzini M., Chemistry 18(46), 2012
PMID: 23019045

Pyykkö, Mol. Phys. 70(), 1990

Veszprémi, Inorg. Chem. 35(), 1996

AUTHOR UNKNOWN, 0

Becker, Z. Anorg. Allg. Chem. 612(), 1992

AUTHOR UNKNOWN, 0

Becker, Z. Anorg. Allg. Chem. 621(), 1995

AUTHOR UNKNOWN, 0

Puschmann, Angew. Chem. 123(), 2011
Phosphination of carbon monoxide: a simple synthesis of sodium phosphaethynolate (NaOCP).
Puschmann FF, Stein D, Heift D, Hendriksen C, Gal ZA, Grutzmacher HF, Grutzmacher H., Angew. Chem. Int. Ed. Engl. 50(36), 2011
PMID: 21766405

Krummenacher, Polyhedron 32(), 2012

Jupp, Angew. Chem. 125(), 2013
The 2-phosphaethynolate anion: a convenient synthesis and [2+2] cycloaddition chemistry.
Jupp AR, Goicoechea JM., Angew. Chem. Int. Ed. Engl. 52(38), 2013
PMID: 23913436

Heift, Dalton Trans. (), 2014

Westerhausen, J. Organomet. Chem. 643-644(), 2002

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Bansal, 2009

Le, Coord. Chem. Rev. 250(), 2006

Weber, Angew. Chem. 114(), 2002

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. 41(), 2002
Organophosphorus pi-conjugated materials.
Baumgartner T, Reau R., Chem. Rev. 106(11), 2006
PMID: 17091932

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Rösch, Z. Naturforsch. B 41(), 1986

Märkl, Tetrahedron Lett. 30(), 1989

Regitz, Angew. Chem. 100(), 1988

AUTHOR UNKNOWN, Angew. Chem. Int. Ed. Engl. 27(), 1988

Annen, Chem. Ber. 123(), 1990

Wrackmeyer, J. Organomet. Chem. 520(), 1996

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0
The conversion of furans into phosphinines.
Mao Y, Mathey F., Chemistry 17(38), 2011
PMID: 21837724

Mao, Organometallics 32(), 2013

Li, Eur. J. Org. Chem. (), 2007

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 1999

AUTHOR UNKNOWN, 0

AUTHOR UNKNOWN, 0

Sieler, Z. Anorg. Allg. Chem. 620(), 1994

Kremer, Organometallics 16(), 1997
Nucleus-Independent Chemical Shifts:  A Simple and Efficient Aromaticity Probe.
Schleyer PVR, Maerker C, Dransfeld A, Jiao H, van Eikema Hommes NJR., J. Am. Chem. Soc. 118(26), 1996
PMID: 28872872
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