Stereochemical Control of Tricoordinate Copper(I) Complexes Based on N-(9-Alkyl-9-fluorenyl)-Substituted Heterocyclic Carbenes

Hamze Almallah; Eric Brenner; Dominique Matt; Christophe Gourlaouen; Muriel Hissler

doi:10.1055/s-0040-1706194

Synthesis, Inhaltsverzeichnis

Synthesis 2021; 53(10): 1785-1794
DOI: 10.1055/s-0040-1706194

paper

Stereochemical Control of Tricoordinate Copper(I) Complexes Based on N-(9-Alkyl-9-fluorenyl)-Substituted Heterocyclic Carbenes

Hamze Almallah

^aLaboratoire de Chimie Inorganique Moléculaire et Catalyse, Institut de Chimie, UMR 7177 CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg cedex, France

,

Eric Brenner∗

^aLaboratoire de Chimie Inorganique Moléculaire et Catalyse, Institut de Chimie, UMR 7177 CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg cedex, France

,

Dominique Matt∗

^aLaboratoire de Chimie Inorganique Moléculaire et Catalyse, Institut de Chimie, UMR 7177 CNRS, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg cedex, France

,

Christophe Gourlaouen

^bLaboratoire de Chimie Quantique, Institut de Chimie, UMR 7177 CNRS, Université de Strasbourg, 1 rue Blaise Pascal, 67008 Strasbourg, France

,

Muriel Hissler

^cInstitut des Sciences Chimiques de Rennes, UMR 6226 CNRS, Université de Rennes 1, Groupe ‘Phosphore et Matériaux Moléculaires’, Campus de Beaulieu, 263 avenue du Général Leclerc, 35042 Rennes Cedex, France

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A series of tricoordinate copper(I) complexes of general formula [Cu(^Et F-NHC)(2,2′-dipyridylamine)][BF₄], in which ^Et F-NHC represents an imidazol-2-ylidene ligand bearing a 9-ethyl-9-fluorenyl N-substituent have been synthesised stepwise from appropriate N-arylimidazoles. All complexes are remarkably air-stable, both in solution and in the solid state. X-ray diffraction studies revealed that in three of the complexes the fluorenylidene plane and the dipyridylamine (dpa) unit undergo intramolecular π–π stacking. The resulting bending of the fluorenilydene plane towards the metal atom is likely to contribute to maintain the trigonal planar geometry of the [Cu–C,N,N] unit upon binding of exogenous substrates, thereby considerably increasing complex stability.

Key words

N-heterocyclic carbenes - bulky ligands - tricoordinate copper(I) complexes - weak interactions

Volltext

Referenzen

References
1 Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485
2 Arduengo AJ, Harlow RL, Kline M. J. Am. Chem. Soc. 1991; 113: 361
3 Herrmann WA, Köcher C. Angew. Chem. Int. Ed. 1997; 36: 2162
4 Hermann WA. Angew. Chem. Int. Ed. 2002; 41: 1290
5 Kantchev EA. B, O’Brien CJ, Organ MG. Angew. Chem. Int. Ed. 2007; 46: 2768
6 Díez-González S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
7 Downing SP, Pogorzelec PJ, Danopoulos AA, Cole-Hamilton DJ. Eur. J. Inorg. Chem. 2009; 1816
8 N-Heterocyclic Carbenes in Synthesis . Nolan SP. Wiley-VCH; Weinheim: 2006
9 Nelson DJ, Nolan SP. Chem. Soc. Rev. 2013; 42: 6723
10 Valente C, Pompeo M, Sayah M, Organ MG. Org. Process Res. Dev. 2014; 18: 180
11 Janssen-Müller D, Schlepphorst C, Glorius F. Chem. Soc. Rev. 2017; 46: 5463
12 Froese RD. J, Lombardi C, Pompeo M, Rucker RP, Organ MG. Acc. Chem. Res. 2017; 50: 2244
13 N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Cazin SJ. Springer Verlag; Berlin: 2011
14 Teci M, Brenner E, Matt D, Toupet L. Eur. J. Inorg. Chem. 2013; 2841
15 Teci M, Brenner E, Matt D, Gourlaouen C, Toupet L. Dalton Trans. 2014; 43: 12251
16 Teci M, Brenner E, Matt D, Toupet L. Z. Kristallogr. New Cryst. Struct. 2014; 229: 169
17 Teci M, Brenner E, Matt D, Gourlaouen C, Toupet L. Chem. Eur. J. 2015; 21: 10997
18 Teci M, Brenner E, Matt D, Gourlaouen C, Toupet L. Dalton Trans. 2015; 44: 9260
19 Teci M, Lentz N, Brenner E, Matt D, Toupet L. Dalton Trans. 2015; 44: 13991
20 Teci M, Hueber D, Pale P, Toupet L, Blanc A, Brenner E, Matt D. Chem. Eur. J. 2017; 23: 7809
21 Krylova VA, Djurovich PI, Whited MT, Thompson ME. Chem. Commun. 2010; 46: 6696
22 Krylova VA, Djurovich PI, Aronson JW, Haiges R, Whited MT, Thompson ME. Organometallics 2012; 31: 7983
23 Marion R, Sguerra F, Di Meo F, Sauvageot E, Lohier JF, Daniellou R, Renaud JL, Linares M, Hamel M, Gaillard S. Inorg. Chem. 2014; 53: 9181
24 Elie M, Sguerra F, Di Meo F, Weber MD, Marion R, Grimault A, Lohier JF, Stallivieri A, Brosseau A, Pansu RB, Renaud JL, Linares M, Hamel M, Costa RD, Gaillard S. ACS Appl. Mater. Interfaces 2016; 8: 14678
25 Hamze R, Peltier JL, Sylvinson D, Jung M, Cardenas J, Haiges R, Soleilhavoup M, Jazzar R, Djurovich PI, Bertrand G, Thompson ME. Science 2019; 363: 601
26 Nicholls TP, Bissember AC. Tetrahedron Lett. 2019; 60: 150883
27 Barluenga J, López LA, Löber O, Tomás M, García-Granda S, Alvarez-Rúa C, Borge J. Angew. Chem. Int. Ed. 2001; 40: 3392
28 Tan GW, Zhu HP. Inorg. Chem. 2011; 50: 6979
29 Lan JB, Chen L, Yu XQ, You JS, Xie RG. Chem. Commun. 2004; 188
30 Chu Y, Deng H, Cheng JP. J. Org. Chem. 2007; 72: 7790
31 Almallah H, Brenner E, Matt D, Harrowfield J, Jahjah M, Hijazi A. Dalton Trans. 2019; 48: 14516
32 Jurkauskas V, Sadighi JP, Buchwald SL. Org. Lett. 2003; 5: 2417
33 CCDC 1960780 (1a) 1960784 (1c) and 1960785 (1e) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
34 Sheldrick GM. Acta Crystallogr., Sect A 2015; 71: 3
35 Sheldrick GM. Acta Crystallogr., Sect C 2015; 71: 3
36 Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA. Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision D.01 . Gaussian, Inc; Wallingford CT: 2009
37 Becke AD. J. Chem. Phy. 1993; 98: 5648
38 Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104
39 Petersson GA, Bennett A, Tensfeldt TG, Allaham MA, Shirley WA, Mantzaris J. J. Chem. Phys. 1988; 89: 2193
40 Fuentealba P, Preuss H, Stoll H, Vonszentpaly L. Chem. Phys. Lett. 1982; 89: 418
41 Contreras-Garcia J, Johnson ER, Keinan S, Chaudret R, Piquemal JP, Beratan DN, Yang WT. J. Chem. Theory Comput. 2011; 7: 625

Zusatzmaterial