Synthesis and Application of N-Heterocyclic Carbene–Palladium Ligands with Glycerol Dendrons for the Suzuki–Miyaura Cross-Coupling in Water

Maike C. Lukowiak; Markus Meise; Rainer Haag

doi:10.1055/s-0034-1378533

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(15): 2161-2165
DOI: 10.1055/s-0034-1378533

letter

Synthesis and Application of N-Heterocyclic Carbene–Palladium Ligands with Glycerol Dendrons for the Suzuki–Miyaura Cross-Coupling in Water

Maike C. Lukowiak

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 eMail: haag@chemie.fu-berlin.de

,

Markus Meise

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 eMail: haag@chemie.fu-berlin.de

,

Rainer Haag*

Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany Fax: +49(30)83853357 eMail: haag@chemie.fu-berlin.de

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Highly active glycerol-dendron-supported N-heterocyclic carbene–palladium catalysts with catalytic sites at the core position were obtained with an efficient modular synthesis. A symmetrical ligand structure was designed to build a larger microenvironment by increasing the number of dendron generations. The catalytic activity was tested in Suzuki–Miyaura cross-coupling reactions. Deprotection of the dendritic supported catalysts allowed the catalytic reaction to take place in neat water, which is highly desirable for a more sustainable processing. A positive dendritic effect was observed for coupling of activated and nonactivated bromoaryls.

Key words

supported catalysis - dendrimers - carbene complexes - palladium - cross-coupling - green chemistry

Volltext

Referenzen

References
1 de Jesús E, Flores JC. Ind. Eng. Chem. Res. 2008; 47: 7968
2 Polymeric Materials in Organic Synthesis and Catalysis. Buchmeiser MR. Wiley-VCH; Weinheim: 2003. VII
3 Oosterom GE, Reek JN. H, Kamer PC. J, van Leeuwen PW. N. M. Angew. Chem. Int. Ed. 2001; 40: 1828
4 Andrés R, de Jesús E, Flores JC. New J. Chem. 2007; 31: 1161
5 Helms B, Fréchet JM. J. Adv. Synth. Catal. 2006; 348: 1125
6 Chow H.-F, Leung C.-F, Wang G.-X, Yang Y.-Y. C. R. Chim. 2003; 6: 735
7 Tomalia DA. New J. Chem. 2012; 36: 264
8 Dahan A, Portnoy M. J. Am. Chem. Soc. 2007; 129: 5860
9 Twyman LJ, King AS. H, Martin IK. Chem. Soc. Rev. 2002; 31: 69
10 Astruc D, Berger A, Chandler BD, Daniel M.-C, Gade LH, Gilbertson JD, Haag R, Hajii C, Kassube JK, Gebbink RJ. M. K, van Koten G, van Leuuwen PW. N. M, Reek JN. H, Ribaudo F, Ruiz J. Dendrimer Catalysis, In Topics in Organometallic Chemistry . Vol. 20. Springer; Berlin: 2006
11 Sommer WJ, Weck M. Coord. Chem. Rev. 2007; 251: 860
12 Glorius F, Bellemin-Laponnaz S, Despagnet-Ayoub E, Díez-González S, Gade LH, Louie J, Nolan SP, Peris E, Ritter T, Rogers MM, Stahl SS, Tekavec TN. N-Heterocyclic Carbenes in Transition Metal Catalysis, In Topics in Organometallic Chemistry . Vol. 21. Springer; Berlin: 2007
13 Meiries S, Le Duc G, Chartoire A, Collado A, Speck K, Arachchige KS. A, Slawin AM. Z, Nolan SP. Chem. Eur. J. 2013; 19: 17358
14 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
15 Ohta H, Fujihara T, Tsuji Y. Dalton Trans. 2008; 379
16 Fujihara T, Yoshida S, Ohta H, Tsuji Y. Angew. Chem. Int. Ed. 2008; 47: 8310
17 Meise M, Haag R. ChemSusChem 2008; 1: 637
18 Kolb HC, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2001; 40: 2004
19 Fernandes AE, Jonas AM, Riant O. Tetrahedron 2014; 70: 1709
20 Bouchmella K, Boury B, Dutremez SG, van der Lee A. Chem. Eur. J. 2007; 13: 6130
21 Wyszogrodzka M, Haag R. Chem. Eur. J. 2008; 14: 9202
22 Herrmann WA, Elison M, Fischer J, Köcher C, Artus GR. J. Angew. Chem., Int. Ed. Engl. 1995; 34: 2371
23 Bourissou D, Guerret O, Gabbaï FP, Bertrand G. Chem. Rev. 2000; 100: 39
24 Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725

Zusatzmaterial

Supporting Information