Gold(I) Complexes Nuclearity in Constrained Ferrocenyl Diphosphines: Dramatic Effect in Gold-Catalyzed Enyne Cycloisomerization.
Functionalized ferrocenes
digold complexes
enyne cyclization
halides
trigonal gold(I)
Journal
Chemistry, an Asian journal
ISSN: 1861-471X
Titre abrégé: Chem Asian J
Pays: Germany
ID NLM: 101294643
Informations de publication
Date de publication:
15 Sep 2020
15 Sep 2020
Historique:
received:
11
05
2020
revised:
16
07
2020
pubmed:
21
7
2020
medline:
21
7
2020
entrez:
21
7
2020
Statut:
ppublish
Résumé
Di-tert-butylated-bis(phosphino)ferrocene ligands bearing phosphino substituents R (R=phenyl, cyclohexyl, iso-propyl, mesityl, or furyl) allow tuning the selective formation of Au(I) halide complexes. Thus, dinuclear linear two-coordinate, but also rare mononuclear trigonal three-coordinate and tetrahedral four-coordinate complexes were formed upon tuning of the conditions. Both Au(I) chloride and rarer Au(I) iodide complexes were synthesized, and their X-ray diffraction analysis are reported. The significance of the control of structure and nuclearity in Au(I) complexes is further illustrated herein by its strong effect on the efficiency and selectivity of gold-catalysed cycloisomerization. Cationic linear digold(I) bis(dicyclohexylphosphino) ferrocenes outperform other catalysts in the demanding regioselective cycloisomerization of enyne sulphonamides into cyclohexadienes. Conversely, tetrahedral and trigonal cationic monogold(I) complexes were found incompetent for enyne cycloaddition. We used the two-coordinate linear electron-rich Au(I) complex 2 b (R=Cy) to extend the scope of selective intramolecular cycloaddition of different 1,6-enyne sulfonylamines with high activity and excellent selectivity to the endo cyclohexadiene products.
Identifiants
pubmed: 32687260
doi: 10.1002/asia.202000579
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2879-2885Subventions
Organisme : ANR
ID : ANR-16-CE07-0007-02
Organisme : CNRS
Organisme : Université de Bourgogne
Organisme : Conseil Régional BFC
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
E. Jimenez-Nunez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326;
Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239;
A. S. K. Hashmi, M. Rudolph, Chem. Soc. Rev. 2008, 37, 1766;
A. Corma, A. Leyva-Perez, M. J. Sabater, Chem. Rev. 2011, 111, 1657;
C. Nieto-Oberhuber, M. Paz Munoz, S. Lopez, E. Jimenez-Nunez, C. Nevado, E. Herrero-Gomez, M. Raducan, A. M. Echavarren, Chem. Eur. J. 2006, 12, 1677.
A. Arcadi, Chem. Rev. 2008, 108, 3266;
A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208;
M. Rudolph, A. S. K. Hashmi, Chem. Soc. Rev. 2012, 41, 2448;
C. Obradors, A. Echavarren, Chem. Commun. 2014, 16.
X. Zhao, M. Rudolph, A. S. K. Hashmi, Chem. Commun. 2019, 55, 12127;
A. Leyva-Pérez, A. Doménech-Carbó, A. Corma, Nat. Commun. 2015, 6, 6703.
D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351;
R. Widenhoefer, Chem. Eur. J. 2008, 14, 5382;
E. Tkatchouk, N. P. Mankad, D. Benitez, W. A. Goddard III, F. D. Toste, J. Am. Chem. Soc. 2011, 133, 14293;
Y. Wang, Z. Wang, Y. Li, G. Wu, Z. Cao, L. Zhang, Nat. Commun. 2015, 5, 4470;
M. Joost, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2015, 54, 15022;
A. Zeineddine, L. Estevez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Nat. Commun. 2017, 8, 565;
N. Dwadnia, J. Roger, N. Pirio, H. Cattey, R. Ben Salem, J.-C. Hierso, Chem. Asian J., 2017, 12, 459.
C. Garcia-Morales, B. Ranieri, I. Escofet, C. Obradors, A. I. Konovalov, A. M. Echavarren, J. Am. Chem. Soc. 2017, 139, 13628. A ferrocenyl diphosphino gold(I) complexes with no aurophilic interactions is reported.
V. Vreeken, D. L. J. Broere, A. C. H. Jans, M. Lankelma, J. N. H. Reek, M. A. Siegler, J. I. van der Vlugt, Angew. Chem. Int. Ed. 2016, 55, 10042;
M. Lankelma, V. Vreeken, M. A. Siegler, J. I. van der Vlugt, Inorganics, 2019, 7, 28.
C.-M. Che, S.-W. Lai, Coord. Chem. Rev. 2005, 249, 1296.
The formation of mononuclear three-coordinate AuI complexes using diphosphines is strongly competed by the formation of dinuclear complexes [LAu(…)AuL], see:
M. Osawa, M.-A. Aino, T. Nagakura, M. Hoshino, Y. Tanaka, M. Akita, Dalton Trans., 2018, 47, 8229;
M. Viotte, B. Gautheron, M. M. Kubicki, Y. Mugnier, R. V. Parish, Inorg. Chem. 1995, 34, 3465; For a recent carbene-stabilized trigonal planar Au(I) complex with a strongly hindering carboranyl-supported diphosphine, see:
A. Zeineddine, F. Rekhroukh, E. D. Sosa Carrizo, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2018, 57, 1306.
Four-coordinate tetrahedral gold(I) complexes synthesized from monophosphine ligands and applications:
P. G. Jones, J. Chem. Soc. Chem. Commun. 1980, 1031;
R. C. Elder, E. H. Kelle Zeiher, M. Onady, R. R. Whittle, J. Chem. Soc. Chem. Commun. 1981, 900;
P. G. Jones, G. M. Sheldrick, J. A. Muir, M. M. Muir, L. B. Pulgar, J. Chem. Soc. Dalton Trans. 1982, 2123;
J. M. Forward, Z. Assefa, R. J. Staples, J. P. Fackler Jr, Inorg. Chem. 1996, 35, 16.
Four-coordinate tetrahedral gold(I) complexes synthesized from chelating diphosphine (or arsine) ligands and applications:
V. W.-W. Yam, C.-L. Chan, S. W.-K. Choi, K. M.-C. Wong, E. C.-C. Cheng, S.-C. Yu, P.-K. Ng, W.-K. Chan, K.-K. Cheung, Chem. Commun. 2000, 53 and references therein;
A. Kaeser, O. Moudam, G. Accorsi, I. Séguy, J. Navarro, A. Belbakra, C. Duhayon, N. Armaroli, B. Delavaux-Nicot, J.-F. Nierengarten, Eur. J. Inorg. Chem. 2014, 1345; For a rare tetracoordinated digold complex, see:
S. A. Bhat, J. T. Mague, M. S. Balakhrishna, Dalton Trans., 2015, 47, 17697;
E. K. Dennis, J. H. Kim, S. Parkin, S. G. Awuah, S. Garneau-Tsodikova, J. Med. Chem. 2020, 63, 2455.
A. Gómez-Suárez, S. Nolan, Angew. Chem. Int. Ed. 2012, 51, 8156.
D. T. Hill, G. R. Girard, F. L. McCabe, R. K. Johnson, P. D. Stupik, J. H. Zhang, W. M. Reiff, D. S. Eggleston, Inorg. Chem. 1989, 28, 529.
M. C. Gimeno, A. Laguna, C. Sarroca, P. G. Jones, Inorg. Chem. 1993, 32, 5926;
F. Canales, M. C. Gimeno, P. G. Jones, A. Laguna, C. Sarroca, Inorg. Chem. 1997, 36, 5206.
A. Houlton, D. M. P. Mingos, D. M. Murphy, D. J. Williams, L.-T. Phang, L. S. A. Hor, J. Chem. Soc. Dalton Trans. 1993, 3629;
P. Lai-Tee, T. S. A. Hor, Z. Zhong-Yuan, T. C. W. Mak, J. Organomet. Chem. 1994, 469, 253.
A. Houlton, R. M. G. Roberts, J. Silver, R. V. Parish, J. Organomet. Chem. 1991, 418, 269.
V. Rampazzi, J. Roger, R. Amardeil, M.-J. Penouilh, P. Richard, J.-C. Hierso, Inorg. Chem. 2016, 55, 10907.
Diastereoselective pure rac synthesis is achieved and used herein, see for details: J. Roger, S. Royer, H. Cattey, A. Savateev, R. V. Smaliy, A. N. Kostyuk, J.-C. Hierso, Eur. J. Inorg. Chem. 2017, 330.
S. F. Hartlaub, N. K. Lauricella, C. N. Ryczek, A. G. Furneaux, J. D. Melton, N. A. Piro, W. S. Kassel, C. Nataro, Eur. J. Inorg. Chem. 2017, 2017, 424;
S. L. Kahn, M. K. Breheney, S. L. Martinak, S. M. Fosbenner, A. R. Seibert, W. S. Kassel, W. G. Dougherty, C. Nataro, Organometallics, 2009, 28, 2119.
A more detailed investigation is needed to fully understand these CV signatures, we envisioned an intramolecular electron transfer (FeIII/FeII)/(2I−/I2).
Only one AuICl complex of this c1 type was reported, obtained with the concomitant formation of its gold dinuclear analogue (25%), see ref. 8b.
In ref. 1e the other substituted sulphonamide 1,6-enynes employed gave conversions >84% in 5 to 30 min, evidencing 6 as a particularly challenging substrate. In general selectivity dropped upon longer reaction time.