Base-Triggered Oxidative Addition to Gold.
DFT calculations
XRD analyses
gold
oxidative addition
secondary phosphine oxides
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
03 Jul 2023
03 Jul 2023
Historique:
received:
05
04
2023
medline:
19
4
2023
pubmed:
19
4
2023
entrez:
19
04
2023
Statut:
ppublish
Résumé
The coordination of secondary phosphine oxides (SPO) was shown to efficiently promote the activation of C(sp
Identifiants
pubmed: 37074869
doi: 10.1002/chem.202301091
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202301091Subventions
Organisme : Centre National de la Recherche Scientifique
Organisme : Agence Nationale de la Recherche
ID : ANR-19-CE07-0037
Organisme : European Commission
ID : Au-MLC - 841877
Organisme : Université de Toulouse
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Références
B. Huang, M. Hu, F. D. Toste, Trends Chem. 2020, 2 707-720.
W. J. Wolf, M. S. Winston, F. D. Toste, Nat. Chem. 2014, 6 159-164;
D. M. Kaphan, M. D. Levin, R. G. Bergman, K. N. Raymond, F. D. Toste, Science 2015, 350 1235-1238;
M. D. Levin, D. M. Kaphan, C. M. Hong, R. G. Bergman, K. N. Raymond, F. D. Toste, J. Am. Chem. Soc. 2016, 138 9682-9693.
M. O. Akram, S. Banerjee, S. S. Saswade, V. Bedi, N. T. Patil, Chem. Commun. 2018, 54, 11069-11083;
S. Banerjee, V. W. Bhoyare, N. T. Patil, Chem. Commun. 2020, 56 2677-2690;
V. W. Bhoyare, A. G. Tathe, A. Das, C. C. Chintawar, N. T. Patil, Chem. Soc. Rev. 2021, 50, 10422-10450;
S. Witzel, A. S. Hashmi, J. Xie, Chem. Rev. 2021, 121, 8868-8925;
P. Font, X. Ribas, Eur. J. Inorg. Chem. 2021, 2556-2569.
J. Guenther, S. Mallet-Ladeira, L. Estevez, K. Miqueu, A. Amgoune, D. Bourissou, J. Am. Chem. Soc. 2014, 136, 1778-1781.
For oxidative addition of C(sp2)−I and strained C−C bonds to gold assisted by N-chelation, see:
J. Serra, T. Parella, X. Ribas, Chem. Sci. 2017, 8, 946-952;
H. Beucher, J. Schörgenhumer, E. Merino, C. Nevado, Chem. Sci. 2021, 12, 15084-15089.
For Rh-catalyzed C−H auration assisted by N-chelation, see: J. Martín, E. Gómez-Bengoa, A. Genoux, C. Nevado, Angew. Chem. Int. Ed. 2022, 61, e202116755;
Angew. Chem. 2021, 134, e202116755.
F. Rekhroukh, R. Brousses, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2015, 54, 1266-1269;
Angew. Chem. 2015, 127, 1282-1285;
F. Rekhroukh, L. Estevez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, J. Am. Chem. Soc. 2016, 138, 11920-11929.
C. Blons, S. Mallet-Ladeira, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2018, 57, 11732-11736;
Angew. Chem. 2018, 130, 11906-11910.
F. Rekhroukh, L. Estévez, C. Bijani, K. Miqueu, A. Amgoune, D. Bourissou, Angew. Chem. Int. Ed. 2016, 55, 3414-3418;
Angew. Chem. 2016, 128, 3475-3479;
F. Rekhroukh, C. Blons, L. Estévez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Chem. Sci. 2017, 8, 4539-4545;
J. Rodriguez, M. S. M. Holmsen, Y. García-Rodeja, E. D. Sosa Carrizo, P. Lavedan, S. Mallet-Ladeira, K. Miqueu, D. Bourissou, J. Am. Chem. Soc. 2021, 143, 11568-11581;
J. Rodriguez, G. Szaloki, E. D. Sosa Carrizo, N. Saffon-Merceron, K. Miqueu, D. Bourissou, Angew. Chem. Int. Ed. 2020, 59, 1511-1515;
Angew. Chem. 2020, 132, 1527-1531.
R. P. Herrera, M. C. Gimeno, Chem. Rev. 2021, 121, 8311-8363.
C. C. Chintawar, A. K. Yadav, A. Kumar, S. P. Sancheti, N. T. Patil, Chem. Rev. 2021, 121, 8478-8558.
N. V. Dubrovina, A. Börner, Angew. Chem. Int. Ed. 2004, 43, 5883-5886;
L. Ackermann, Synthesis 2006, 10, 1557-1571;
P. Sutra, A. Igau, Coord. Chem. Rev. 2016, 308, 97-116;
J. Francos, D. Elorriaga, P. Crochet, V. Cadierno, Coord. Chem. Rev. 2019, 387, 199-234;
A. Gallen, A. Riera, X. Verdaguer, A. Grabulosa, Catal. Sci. Technol. 2019, 9, 5504-5561.
H. Schmidbaur, M. A. Aly, Angew. Chem. Int. Ed. Engl. 1980, 19, 71-72;
Angew. Chem. 1980, 92, 66-67;
C. Hollatz, A. Schier, H. Schmidbaur, J. Am. Chem. Soc. 1997, 119, 8115-8116;
C. Hollatz, A. Schier, H. Schmidbaur, Chem. Ber. 1997, 130, 1333-1338;
C. Hollatz, A. Schier, J. Riede, H. Schimdbaur, J. Chem. Soc. Dalton Trans. 1999, 111-113;
J. Vicente, M. T. Chicote, P. G. Jones, Inorg. Chem. 1993, 32, 4960-4964;
W. J. Hunks, M. C. Jennings, R. J. Puddephatt, Inorg. Chem. 2000, 39, 2699-2702.
F. Schröder, C. Tugny, E. Salanouve, H. Clavier, L. Giordano, D. Moraleda, Y. Gimbert, V. Mouries-Mansuy, J. P. Goddard, L. Fensterbank, Organometallics 2014, 33, 4051-4056.
The available O atom is presumed to cooperate with Au to cleave and transfer dihydrogen:
I. Cano, M. A. Huertos, A. M. Chapman, G. Buntkowsky, T. Gutmann, P. B. Groszewicz, P. W. N. M. Van Leeuwen, J. Am. Chem. Soc. 2015, 137, 7718-7727;
Y. Wang, X. H. Liu, R. Wang, B. Cula, Z. N. Chen, Q. Chen, N. Koch, N. Pinna, J. Am. Chem. Soc. 2021, 143, 9595-9600.
L. Rocchigiani, M. Bochmann, Chem. Rev. 2021, 121, 8364-8451.
See Supporting Information for details.
Deposition Numbers 2212158 (for 3’), 2212155 (for 5 a), 2212157 (for 5 b) and 2212160 (for 7 b) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
A similar situation was found previously in (RR’(HO)P)AuCl and (phosphine-NHCOCF3)AuCl complexes, see Ref. [10] and S. Sen, F. P. Gabbaï, Chem. Commun. 2017, 53, 13356-13358.
For a compilation and comparison of bay angles in P,C-cyclometalated complexes deriving from naphthyl phosphines, see: J. Monot, E. Marelli, B. Martin-Vaca, D. Bourissou, Chem. Soc. Rev. doi:10.1039/d2cs00564f.
M. Joost, A. Zeineddine, L. Estévez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, J. Am. Chem. Soc. 2014, 136, 14654-14657;
A. Zeineddine, L. Estevez, S. Mallet-Ladeira, K. Miqueu, A. Amgoune, D. Bourissou, Nat. Commun. 2017, 8, 565;
J. Rodriguez, A. Zeineddine, E. D. Sosa Carrizo, K. Miqueu, N. Saffon-Merceron, A. Amgoune, D. Bourissou, Chem. Sci. 2019, 10, 7183-7192.
M. J. Harper, C. J. Arthur, J. Crosby, E. J. Emmett, R. L. Falconer, A. J. Fensham-Smith, P. J. Gates, T. Leman, J. E. McGrady, J. F. Bower, C. A. Russell, J. Am. Chem. Soc. 2018, 140, 4440-4445;
J. A. Cadge, J. F. Bower, C. A. Russell, Angew. Chem. Int. Ed. 2021, 60, 24976-24983;
Angew. Chem. 2021, 133, 25180-25187.
Oxidative addition is a priori feasible thermally for complex 3 as well, but the degradation observed experimentally upon heating suggests some side-reaction competes with the formation of the Au(III) complex 6 in this case.
Redox non-innocence resulting in peripheral C−C coupling was reported for a dinuclear gold complex derived from a P N P ligand, see:
V. Vreeken, D. l. 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, 10042-10046; Angew. Chem. 2016, 128, 10196-10200;
V. Vreeken, M. A. Siegler, J. I. van der Vlugt, Chem. Eur. J. 2017, 23, 5585-5594.
C. F. Czauderna, A. M. Z. Slawin, D. B. Cordes, J. I. van der Vlugt, P. C. J. Kamer, Tetrahedron 2019, 75, 47-56.
G. M. Sheldrick Acta Crystallogr. Sect. A 2015, 71, 3-8.
G. M. Sheldrick Acta Crystallogr. Sect. C 2015, 71, 3-8.
Gaussian 16, Revision B.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D. J. Fox, Gaussian, Inc., Wallingford CT, 2016.
A. D. Becke J. Chem. Phys. 1993, 98, 5648-5652;
J. P. Perdew, in Electronic Structure of Solids ‘91, Ed. P. Ziesche, H. Eschrig, Akademie Verlag, Berlin, 1991, 11.
D. Andrae, U. Häussermann, M. Dolg, H. Stoll, H. Preuss, Theor. Chim. Acta 1990, 77, 123-141.
A. W. Ehlers, M. Biihme, S. Dapprich, A. Gobbi, A. Hijllwarth, V. Jonas, K. F. Kiihler, R. Stegmann, A. Veldkamp, G. Frenking, Chem. Phys. Lett. 1993, 208, 111-114.
K. Fukui, Acc. Chem. Res. 1981, 14, 363-368;
H. P. Hratchian, H. B. Schlegel, in Theory and Applications of Computational Chemistry: The First 40 Years, Ed. C. E. Dykstra, G. Frenking, K. S. Kim, G. Scuseria, Elsevier, Amsterdam, 2005, 195.
S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104;
S. Grimme, S. Ehrlich, L. Goerigk, J. Comput. Chem. 2011, 32, 1456-1465.
K. Morokuma, J. Chem. Phys. 1971, 55, 1236-1244;
T. Ziegler, A. Rauk, Theor. Chim. Acta 1977, 46, 1-10.
E. J. Baerends, T. Ziegler, J. Autschbach, D. Bashford, A. Bérces, F. M. Bickelhaupt, C. Bo, P. M. Boerrigter, L. Cavallo, D. P. Chong, L. Deng, R. M. Dickson, D. E. Ellis, M. van Faassen, L. Fan, T. H. Fischer, C. Fonseca Guerra, M. Franchini, A. Ghysels, A. Giammona, S. J. A. van Gisbergen, A. W. Götz, J. A. Groeneveld, O. V. Gritsenko, M. Grüning, S. Gusarov, F. E. Harris, P. van den Hoek, C. R. Jacob, H. Jacobsen, L. Jensen, J. W. Kaminski, G. van Kessel, F. Kootstra, A. Kovalenko, M. V. Krykunov, E. van Lenthe, D. A. McCormack, A. Michalak, M. Mitoraj, S. M. Morton, J. Neugebauer, V. P. Nicu, L. Noodleman, V. P. Osinga, S. Patchkovskii, M. Pavanello, P. H. T. Philipsen, D. Post, C. C. Pye, W. Ravenek, J. I. Rodríguez, P. Ros, P. R. T. Schipper, H. van Schoot, G. Schreckenbach, J. S. Seldenthuis, M. Seth, J. G. Snijders, M. Solà, M. Swart, D. Swerhone, G. te Velde, P. Vernooijs, L. Versluis, L. Visscher, O. Visser, F. Wang, T. A. Wesolowski, E. M. van Wezenbeek, G. Wiesenekker, S. K. Wolff, T. K. Woo, A. L. Yakovle, ADF 2019, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com.
M. Mitoraj, A. Michalak, T. Ziegler, J. Chem. Theory Comput. 2009, 5, 962-975.