Insights into Copper-Poly(pyrazolyl)methane-Catalyzed Reactions for Organic Transformations

Julian Moegling; Alexander Hoffmann; Sonja Herres-Pawlis

doi:10.1055/s-0036-1588892

Synthesis, Table of Contents

Synthesis 2017; 49(02): 225-236
DOI: 10.1055/s-0036-1588892

short review

Insights into Copper-Poly(pyrazolyl)methane-Catalyzed Reactions for Organic Transformations

Julian Moegling

Lehrstuhl für Bioanorganische Chemie, Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: sonja.herres-pawlis@ac.rwth-aachen.de

,

Alexander Hoffmann

Lehrstuhl für Bioanorganische Chemie, Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: sonja.herres-pawlis@ac.rwth-aachen.de

,

Sonja Herres-Pawlis*

Lehrstuhl für Bioanorganische Chemie, Institut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany Email: sonja.herres-pawlis@ac.rwth-aachen.de

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Abstract

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Dedicated to Prof. Dr. Dieter Enders on the occasion of his 70^th birthday

Abstract

Copper-poly(pyrazolyl)methane complexes have been proven to be highly useful in a variety of catalytic organic transformations. A multitude of poly(pyrazolyl)methane ligands have been developed for this effort and are summarized in this work. Their tailored electronic properties and steric hindrance are easily modified, demonstrating their diversity and high potential as spectator ligands for copper catalysis. The listed examples of organic reactions range from cycloadditions to nitrene transfer and bioinorganic monooxygenase chemistry.

1 Introduction

2 Cycloadditions of Azides and Alkynes

3 Copper-Mediated Nitrene and Carbene Transfer

4 C_sp–C_sp2, C–N and C–S Cross-Coupling Reactions

5 Copper–Tpm-Catalyzed Aldol Reactions

6 A Bpm Ligand for the Polymerization of Methyl Methacrylate

7 Copper-Catalyzed Oxidations

8 Concluding Remarks

Key words

copper - N ligands - pyrazole - oxidation - cycloaddition - cross-coupling - polymerization - aldol

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References

References

1a Trofimenko S. Chem. Rev. 1993; 93: 943
1b Trofimenko S. J. Chem. Educ. 2005; 82: 1715

2a Byers PK, Canty AJ, Honeyman RT. J. Organomet. Chem. 1990; 385: 417
2b Reger DL. Comments Inorg. Chem. 1999; 21: 1
2c Otero A, Fernández-Baeza J, Antiñolo A, Tejeda J, Lara-Sánchez A. Dalton Trans. 2004; 1499
2d Pettinari C, Pettinari R. Coord. Chem. Rev. 2005; 249: 525
2e Pettinari C, Pettinari R. Coord. Chem. Rev. 2005; 249: 663
2f Reger DL, Semeniuc JR, Gardinier JR, O’Neal J, Reinecke B, Smith MD. Inorg. Chem. 2006; 45: 4337
2g Hoffmann A, Flörke U, Schürmann M, Herres-Pawlis S. Eur. J. Org. Chem. 2010; 4136
2h Krieck S, Koch A, Hinze K, Müller C, Lange J, Görls H, Westerhausen M. Eur. J. Inorg. Chem. 2016; 2332
2i Martins LM. D. R. S, Pombeiro AJ. L. Coord. Chem. Rev. 2014; 265: 74
2j Otero A, Fernández-Baeza J, Lara-Sánchez A, Sánchez-Barba LF. Coord. Chem. Rev. 2013; 257: 1806
2k Bigmore HR, Lawrence SC, Mountford P, Tredget CS. Dalton Trans. 2005; 635
2l Martins LM. D. R. S, Pombeiro AJ. L. Eur. J. Inorg. Chem. 2016; 2236
2m Semeniuc RF, Reger DL. Eur. J. Inorg. Chem. 2016; 2253
2n Manzano BR, Jalón FA, Carrión MC, Durá G. Eur. J. Inorg. Chem. 2016; 2272

3 Cano I, Nicasio MC, Pérez PJ. Org. Biomol. Chem. 2010; 8: 536

4a Wang F, Fu H, Jiang Y, Zhao Y. Adv. Synth. Catal. 2008; 350: 1830
4b Liu Y, Wang X, Xu J, Zhang Q, Zhao Y, Hu Y. Tetrahedron 2011; 67: 6294
4c Wang K, Xing S, Liao P, Fang Z, Meng X, Zhang Q, Liu Q, Ji Y. Green Chem. 2011; 13: 562
4d Longqiang X, Shaojun C, Liu Q, Liao L, Guo X, Li Y, Jia X, Li F, Liu L. Polym. Chem. 2014; 5: 607
4e Saha S, Kaur M, Bera JK. Organometallics 2015; 34: 3047

5a Cano I, Álvarez E, Nicasio MC, Pérez PJ. J. Am. Chem. Soc. 2011; 133: 191
5b Haldón E, Besora M, Cano I, Cambeiro XC, Pericàs MA, Maseras F, Nicasio MC, Pérez PJ. Chem. Eur. J. 2014; 20: 3463

6a Rodríguez P, Caballero A, Díaz-Requejo M, Nicasio MC, Pérez PJ. Org. Lett. 2006; 8: 557
6b Rodríguez P, Álvarez E, Nicasio MC, Pérez PJ. Organometallics 2007; 26: 6661

7 Cano I, Nicasio MC, Pérez PJ. Dalton Trans. 2009; 730
8 Wilkes JS, Levisky JA, Wilson RA, Hussey CL. Inorg. Chem. 1982; 21: 1263
9 Godau T, Bleifuß SM, Müller AL, Roth T, Hoffmann S, Heinemann FW, Burzlaff N. Dalton Trans. 2011; 40: 6547
10 Haldón E, Álvarez E, Nicasio MC, Pérez PJ. Inorg. Chem. 2012; 51: 8298
11 Moegling J, Benischke AD, Hammann JM, Vepřek NA, Zoller F, Rendenbach B, Hoffmann A, Sievers H, Schuster M, Knochel P, Herres-Pawlis S. Eur. J. Org. Chem. 2015; 7475
12 Rocha BG. M, MacLeod TC. O, Guedes da Silva MF. C, Luzyanin KV, Martins LM. D. R. S, Pombeiro AJ. L. Dalton Trans. 2014; 43: 15192
13 Liu G.-F, Li L.-L, Ren Z.-G, Li H.-X, Cheng Z.-P, Zhu J, Zhu X.-L, Lang J.-P. Macromol. Chem. Phys. 2009; 210: 1654

14a Tolman WB, Que LJr. Nature 2008; 455: 333
14b Rolff M, Schottenheim J, Decker H, Tuczek F. Chem. Soc. Rev. 2011; 40: 4077
14c Solomon EI, Heppner DE, Johnston EM, Ginsbach JW, Cirera J, Qayyum M, Kieber-Emmons MT, Kjaergaard CH, Hadt RG, Tian L. Chem. Rev. 2014; 114: 3659
14d Citek C, Herres-Pawlis S, Stack TD. P. Acc. Chem. Res. 2015; 48: 2424

15 Fujisawa K, Ono T, Ishikawa Y, Amir N, Miyashita Y, Okamoto K, Lehnert N. Inorg. Chem. 2006; 45: 1698
16 Costas M, Llobet A. J. Mol. Catal. 1999; 142: 113

17a Silva TF. S, Alegria EC. B. A, Martins LM. D. R. S, Pombeiro AJ. L. Adv. Synth. Catal. 2008; 350: 706
17b Silva TF. S, Mishra GS, Guedes da Silva MF, Wanke R, Martins LM. D. R. S, Pombeiro AJ. L. Dalton Trans. 2009; 9207
17c Silva TF. S, Rocha BG. M, Guedes da Silva MF, Martins LM. D. R. S, Pombeiro AJ. L. New J. Chem. 2016; 40: 528
17d Martins LM. D. R. S, Pombeiro AJ. L In Advances in Organometallic Chemistry and Catalysis, The Silver/Gold Jubilee ICOMC Celebratory Book . 1st ed.; Pombeiro AJ. L. Wiley & Sons; Hoboken: 2014: 285
17e Schuchardt U, Cardoso D, Sercheli R, Pereira R, da Cruz RS, Guerreiro MC, Mandelli D, Spinacé EV, Pires EL. Appl. Catal. 2001; 211: 1

18 Schepetkin I, Potapov A, Khlebnikov A, Korotkova E, Lukina A, Malovichko G, Kirpotina L, Quinn MT. J. Biol. Inorg. Chem. 2006; 11: 499
19 Gajewska MJ, Ching W.-M, Wen Y.-S, Hung C.-H. Dalton Trans. 2014; 43: 14726
20 Quideau S, Deffieux D, Pouysegu L In Comprehensive Organic Synthesis II . 2nd ed.; Knochel P. Elsevier; Amsterdam: 2014: 656

21a Hoffmann A, Citek C, Binder S, Goos A, Rübhausen M, Troeppner O, Ivanović-Burmazović I, Wasinger EC, Stack TD. P, Herres-Pawlis S. Angew. Chem. Int. Ed. 2013; 52: 5398
21b Wilfer C, Liebhäuser P, Erdmann H, Hoffmann A, Herres-Pawlis S. Eur. J. Inorg. Chem. 2015; 494
21c Wilfer C, Liebhäuser P, Hoffmann A, Erdmann H, Grossmann O, Runtsch L, Paffenholz E, Schepper R, Dick R, Bauer M, Dürr M, Ivanović-Burmazović I, Herres-Pawlis S. Chem. Eur. J. 2015; 21: 17639

22a Hamann JN, Schneider R, Tuczek F. J. Coord. Chem. 2015; 68: 3259
22b Rolff M, Schottenheim J, Peters G, Tuczek F. Angew. Chem. Int. Ed. 2010; 49: 6438 ; Angew. Chem. 2010, 122, 6583

23a Esguerra KV. N, Fall J, Petitjean L, Lumb J.-P. J. Am. Chem. Soc. 2014; 136: 7662
23b Huang Z, Askari MS, Esguerra KV. N, Dai T.-Y, Kwon O, Ottenwaelder X, Lumb J.-P. Chem. Sci. 2016; 7: 358

24a Hoffmann A, Herres-Pawlis S. Chem. Commun. 2014; 50: 403
24b Hoffmann A, Herres-Pawlis S. Phys. Chem. Chem. Phys. 2016; 18: 6430