European Journal of Chemistry 2019, 10(2), 171-174. doi:10.5155/eurjchem.10.2.171-174.1865
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Synthesis and crystallographic structure of nickel(0) carbonyl complex with Bitianp, an atropoisomeric diphosphine


Marco Fusè (1) orcid , Giorgio Facchetti (2) orcid , Isabella Rimoldi (3) orcid , Carlo Castellano (4,*) orcid

(1) Scuola Normale Superiore, Piazza dei Cavalieri 7, 56126 Pisa, Italia
(2) Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italia
(3) Dipartimento di Scienze Farmaceutiche, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italia
(4) Dipartimento di Chimica, Università degli Studi di Milano, Via Golgi 19, 20133 Milano, Italia
(*) Corresponding Author

Received: 02 Apr 2019, Accepted: 19 May 2019, Published: 30 Jun 2019

Abstract


The reaction between an atropoisomeric diphosphine, Bitianp and [Ni(CO)4] was achieved by direct condensation in CH3Cl to afford complexes of general formula [Ni(CO)2(Bitianp)]. This compound was characterized by elemental analysis, IR, 1H-, 13C- and 31P-NMR spectroscopies. The structure of nickel complex has been determined by X-ray crystal-lography. Crystal data for C42H28NiO2P2S2 (= 749.41 g/mol): triclinic, space group P-1 (no. 2), a = 10.539(2) Å, b = 11.811(2) Å, c = 15.994(3) Å, α = 83.93(3)°, β = 88.18(3)°, γ = 65.24(3)°, = 1797.6(7) Å3, Z  = 2, T  = 294(2) K, μ(MoKα) = 0.781 mm-1, Dcalc =1.385 g/cm3, 22744 reflections measured (2.56° ≤ 2Θ ≤ 64.726°), 11837 unique (Rint = 0.0157, Rsigma = 0.0215) which were used in all calculations. The final R1 was 0.0360 (I > 2σ(I)) and wR2 was 0.1088 (all data). The coordination sphere of the Ni center is best described as a tetrahedral geometry.


Keywords


Carbonyl; Sigma donor; Envelope ring; Nickel complex; Tetrahedral geometry; Atropoisomeric diphosphine

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DOI: 10.5155/eurjchem.10.2.171-174.1865

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References

[1]. Blaser, H. U.; Scmidt, E. Asymmetric Catalysis on Industrial Scale. Wiley-VCH Verlag GmbH &Co, 2004.
https://doi.org/10.1002/3527602151

[2]. Li, Y. M.; Kwong, F. Y.; Yu, W. Y.; Chan, A. S. C. Coord. Chem. Rev. 2007, 251, 2119-2144.
https://doi.org/10.1016/j.ccr.2007.07.020

[3]. Luhr, S.; Holz, J.; Börner, A. Chem. Cat. Chem. 2011, 3, 1708-1730.
https://doi.org/10.1002/cctc.201100164

[4]. Ager, D. J.; de Vries, A. H.; de Vries, J. G. Chem Soc Rev 2012, 41, 3340-80.
https://doi.org/10.1039/c2cs15312b

[5]. Zerla, D. S.; Rimoldi, I.; Cesarotti, E.; Facchetti, G.; Pellizzoni, M.; Fuse M. J. Organomet. Chem. 2014, 771, 2-8.
https://doi.org/10.1016/j.jorganchem.2014.06.016

[6]. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem. Int. Ed. 2005, 44, 5384-5427.
https://doi.org/10.1002/anie.200462661

[7]. Miyashita, A.; Takaya, H.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245-1253.
https://doi.org/10.1016/S0040-4020(01)82411-X

[8]. Cesarotti, E.; Abbiati, G.; Rossi, E.; Spalluto, P.; Rimoldi, I. Tetrahedron: Asym. 2008, 19, 1654-1659.
https://doi.org/10.1016/j.tetasy.2008.07.009

[9]. Cesarotti, E.; Rimoldi, I.; Spalluto, P.; Demartin, F. Tetrahedron: Asym. 2007, 18, 1278-1283.
https://doi.org/10.1016/j.tetasy.2007.04.018

[10]. Li, Y.; Zhou, Y.; Shi, Q.; Ding, K.; Noyori, R.; Sandoval, C. A. Adv. Synth. Catal. 2011, 353, 495-500.
https://doi.org/10.1002/adsc.201000577

[11]. Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem. Int. Ed. 1998, 37, 1703-1707.
https://doi.org/10.1002/(SICI)1521-3773(19980703)37:12<1703::AID-ANIE1703>3.0.CO;2-I

[12]. Bringmann, G.; Scharl, H.; Maksimenka, K.; Radacki, K.; Braunschweig, H.; Wich, P.; Schmuck, C. Eur. J. Org. Chem. 2006, 2006, 4349-4361.
https://doi.org/10.1002/ejoc.200600311

[13]. Qiu, L.; Kwong, F. Y.; Wu, J.; Lam, W. H.; Chan, S.; Yu, W.-Y.; Li, Y.-M.; Guo, R.; Zhou, Z.; Chan, A. S. C. J. Am. Chem. Soc. 2006, 128, 5955-5965.
https://doi.org/10.1021/ja0602694

[14]. Rimoldi, I.; Pellizzoni, M.; Facchetti, G.; Molinari, F.; Zerla, D.; Gandolfi, R. Tetrahedron: Asym. 2011, 22, 2110-2116.
https://doi.org/10.1016/j.tetasy.2011.11.017

[15]. Facchetti, G.; Bucci, R.; Fusè, M.; Rimoldi, I. Chem. Select 2018, 3, 8797-8800.
https://doi.org/10.1002/slct.201802223

[16]. Rimoldi, I.; Facchetti, G.; Cesarotti, E.; Pellizzoni, M.; Fuse, M.; Zerla, D. Curr. Org. Chem. 2012, 16, 2982-2988.
https://doi.org/10.2174/138527212804546714

[17]. Zerla, D.; Facchetti G.; Fuse M.; Pellizzoni, M.; Castellano, C.; Cesarotti, E.; Gandolfi, R.; Rimoldi, I. Tetrahedron: Asym. 2014, 25, 1031-1037.
https://doi.org/10.1016/j.tetasy.2014.06.003

[18]. Spielvogel, D. J.; Buchwald, S. L., J. Am. Chem. Soc. 2002, 124, 3500-3501.
https://doi.org/10.1021/ja017545t

[19]. Ghosh, A.; Walker, J. A.; Ellern, A.; Stanley, L. M. ACS Catal. 2016, 6, 2673-2680.
https://doi.org/10.1021/acscatal.6b00365

[20]. Marelli, E.; Fernandez Salas, J. A.; Nolan, S. P. Synthesis 2015, 47, 2032-2037.
https://doi.org/10.1055/s-0034-1380813

[21]. Koch, E.; Takise, R.; Studer, A.; Yamaguchi, J.; Itami, K. Chem. Commun. 2015, 51, 855-857.
https://doi.org/10.1039/C4CC08426H

[22]. Facchetti, G.; Cesarotti, E.; Pellizzoni, M.; Zerla, D.; Rimoldi, I. Eur. J. Inorg. Chem. 2012, 2012, 4365-4370.
https://doi.org/10.1002/ejic.201200643

[23]. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2953-2956.
https://doi.org/10.1021/ja00713a006

[24]. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694-3703.
https://doi.org/10.1021/ja9721881

[25]. Fuse, M.; Rimoldi, I.; Cesarotti, E.; Rampino, S.; Barone, V. Phys. Chem. Chem. Phys. 2017, 19, 9028-9038
https://doi.org/10.1039/C7CP00982H

[26]. Mazzeo, G.; Fusè, M.; Longhi, G.; Rimoldi, I.; Cesarotti, E.; Crispini, A.; Abbate, S. Dalton Trans. 2016, 45, 992-999
https://doi.org/10.1039/C5DT03642A

[27]. Fusè, M.; Rimoldi, I.; Facchetti, G.; Rampino, S.; Barone, V. Chem. Commun. 2018, 54, 2397-2400.
https://doi.org/10.1039/C7CC09627E

[28]. Flener Lovitt, C.; Frenking, G.; Girolami, G. S. Organometal. 2012, 31, 4122-4132.
https://doi.org/10.1021/om200456j

[29]. Liang, L. C.; Hung, Y. T.; Huang, Y. L.; Chien, P. S.; Lee, P. Y.; Chen, W.-C. Organometal. 2012, 31, 700-708.
https://doi.org/10.1021/om201041z

[30]. Benincori, T.; Brenna, E.; Sannicolò, F.; Trimarco, L.; Antognazza, P.; Cesarotti, E.; Demartin, F.; Pilati, T. J. Org. Chem. 1996, 61, 6244-6251.
https://doi.org/10.1021/jo960211f

[31]. Abbate, S.; Castiglione, F.; Lebon, F.; Longhi, G.; Longo, A.; Mele, A.; Panzeri, W.; Ruggirello, A.; Liveri, V. T. J. Phys. Chem. B 2009, 113, 3024-3033.
https://doi.org/10.1021/jp809793u

[32]. SADABS Area-Detector Absorption Correction Program, B. A. I. M., WI, USA 2000.

[33]. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallog. 1999, 32, 115-119.
https://doi.org/10.1107/S0021889898007717

[34]. Sheldrick, G. M. Acta Cryst. C 2015, 71, 3-8.
https://doi.org/10.1107/S2053229614024218

[35]. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
https://doi.org/10.1107/S0021889899006020

[36]. Manceron, L.; Alikhani, M. E. Chem. Phys. 1999, 244, 215-226.
https://doi.org/10.1016/S0301-0104(99)00110-X

[37]. Colombo, A.; Dragonetti, C.; Magni, M.; Roberto, D.; Demartin, F.; Caramori, S.; Bignozzi, C. A. ACS Appl. Mater. Interfaces 2014, 6, 13945-13955.
https://doi.org/10.1021/am503306f

[38]. Okuniewski, A.; Rosiak, D.; Chojnacki, J.; Becker, B. Polyhedron 2015, 90, 47-57.
https://doi.org/10.1016/j.poly.2015.01.035


How to cite


Fusè, M.; Facchetti, G.; Rimoldi, I.; Castellano, C. Eur. J. Chem. 2019, 10(2), 171-174. doi:10.5155/eurjchem.10.2.171-174.1865
Fusè, M.; Facchetti, G.; Rimoldi, I.; Castellano, C. Synthesis and crystallographic structure of nickel(0) carbonyl complex with Bitianp, an atropoisomeric diphosphine. Eur. J. Chem. 2019, 10(2), 171-174. doi:10.5155/eurjchem.10.2.171-174.1865
Fusè, M., Facchetti, G., Rimoldi, I., & Castellano, C. (2019). Synthesis and crystallographic structure of nickel(0) carbonyl complex with Bitianp, an atropoisomeric diphosphine. European Journal of Chemistry, 10(2), 171-174. doi:10.5155/eurjchem.10.2.171-174.1865
Fusè, Marco, Giorgio Facchetti, Isabella Rimoldi, & Carlo Castellano. "Synthesis and crystallographic structure of nickel(0) carbonyl complex with Bitianp, an atropoisomeric diphosphine." European Journal of Chemistry [Online], 10.2 (2019): 171-174. Web. 7 Dec. 2019
Fusè, Marco, Facchetti, Giorgio, Rimoldi, Isabella, AND Castellano, Carlo. "Synthesis and crystallographic structure of nickel(0) carbonyl complex with Bitianp, an atropoisomeric diphosphine" European Journal of Chemistry [Online], Volume 10 Number 2 (30 June 2019)

DOI Link: https://doi.org/10.5155/eurjchem.10.2.171-174.1865

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