RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2018; 29(15): 1957-1977
DOI: 10.1055/s-0037-1610156
DOI: 10.1055/s-0037-1610156
account
Guanidines as Reagents in Proton-Coupled Electron-Transfer Reactions and Redox Catalysts
Continuous financial support by the Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged.
Weitere Informationen
Publikationsverlauf
Received: 29. März 2018
Accepted after revision: 02. Mai 2018
Publikationsdatum:
08. Juni 2018 (online)
Abstract
Redox-active guanidines are ideal proton-coupled electron-transfer (PCET) reagents, since they combine a high Brønsted basicity with a low and tunable redox potential. In this article, the development of redox-active guanidines (especially guanidino-functionalized aromatics, GFAs) in the last ten years is summarized, and their properties compared to other organic Brønsted bases and organic electron donors. First, some applications in organic chemistry that purely use the redox activity (formation of organic donor–acceptor materials and photochemical reductive C–C coupling reactions) are presented. Then, reactions that involve both proton and electron transfer are reviewed. In stoichiometric reactions, redox-active guanidines are used for the dehydrogenative coupling of thiols and phosphanes. The first redox catalytic applications are discussed, using dioxygen as green oxidizing reagent.
1 Introduction
2 Redox-Active Amines and Guanidines
3 Brønsted Basicity of Amines and Guanidines
4 Variations of GFA Compounds
5 GFA Compounds in Organic Donor–Acceptor Materials and as Reducing Reagents in Organic Synthesis
6 Stoichiometric Dehydrogenative Coupling Reactions with Redox-Active Guanidines
7 Guanidines as Redox Catalysts
8 Conclusions and Outlook
-
References
- 2 Hammes-Schiffer S. Soudackov AV. J. Phys. Chem. B 2008; 112: 14108
- 3a Elgrishi N. McCarthy BD. Rountree ES. Dempsey JL. ACS Catal. 2016; 6: 3644
- 3b McCarthy BD. Dempsey JL. Inorg. Chem. 2017; 56: 1225
- 4 Proton-Coupled Electron Transfer: A Carrefour of Chemical Reactivity Traditions . Formosinho S. Barroso M. RSC Catalysis Series No. 8, RSC Publishing; Cambridge: 2012
- 5 Reece SY. Hodgkiss JM. Stubbe JA. Nocera DG. Philos. Trans. R. Soc., B 2006; 361: 1351
- 6 Kumar M. Sinha A. Francisco JS. Acc. Chem. Res. 2016; 49: 877
- 7a Salamone M. Bietti M. Acc. Chem. Res. 2015; 48: 2895
- 7b Gentry EC. Knowles RR. Acc. Chem. Res. 2016; 49: 1546
- 8 Pourbaix M. Atlas d’Equilibres Electrochemiques . Ganthier-Villars; Paris: 1963
- 9 Freys JC. Bernardinelli G. Wenger OS. Chem. Commun. 2008; 4267
- 10 Wenger OS. Acc. Chem. Res. 2013; 46: 1517
- 11 Eisenhart TT. Dempsey JL. J. Am. Chem. Soc. 2014; 136: 12221
- 12 Lai W. Li C. Chen H. Shaik S. Angew. Chem Int. Ed. 2012; 51: 5556 ; Angew. Chem. 2012, 124, 5652
- 13 Dietl N. Schlangen M. Schwarz H. Angew. Chem. Int. Ed. 2012; 51: 5144 ; Angew. Chem. 2012, 124, 5638
- 14 Cowley RE. Eckert NA. Vaddadi S. Figg TM. Cundari TR. Holland PL. J. Am. Chem. Soc. 2011; 133: 9796
- 15 Choi GJ. Zhu Q. Miller DC. Gu CJ. Knowles RR. Nature 2016; 539: 268
- 16 Jeffery JL. Terrett JA. MacMillan DW. C. Science 2015; 349: 1532
- 17 Sen VD. Golubev VA. J. Phys. Org. Chem. 2009; 22: 138
- 18 Amorati R. Pedulli GF. Pratt DA. Valgimigli L. Chem. Commun. 2010; 46: 5139
- 19a Recupero F. Punta C. Chem. Rev. 2007; 107: 3800
- 19b Galli C. Gentili P. Lanzalunga O. Angew. Chem. Int. Ed. 2008; 47: 4790 ; Angew. Chem. 2008, 120, 4868
- 20 Wendlandt AE. Stahl SS. Angew. Chem. Int. Ed. 2015; 54: 14638 ; Angew. Chem. 2015, 127, 14848
- 21a Piera J. Bäckvall J.-E. Angew. Chem. Int. Ed. 2008; 47: 3506 ; Angew. Chem. 2008, 120, 3558
- 21b Ventura-Espinosa D. Mata JA. Eur. J. Inorg. Chem. 2016; 17: 2667
- 22a Wang G.-Z. Andreasson U. Bäckvall J.-E. J. Chem. Soc., Chem. Commun. 1994; 1037
- 22b Csjernyik G. Éll AH. Fadini L. Pugin B. Bäckvall J.-E. J. Org. Chem. 2002; 67: 1657
- 22c Samec JS. M. Éll AH. Bäckvall J.-E. Chem. Eur. J. 2005; 11: 2327
- 22d Endo Y. Bäckvall J.-E. Chem. Eur. J. 2011; 17: 12596
- 22e Babu BP. Endo Y. Bäckvall J.-E. Chem. Eur. J. 2012; 18: 11524
- 22f Endo Y. Bäckvall J.-E. Chem. Eur. J. 2012; 18: 13609
- 23a Selmeczi K. Réglier M. Giorgi M. Speier G. Coord. Chem. Rev. 2003; 245: 191
- 23b Simándi LI. Simándi TM. May Z. Besenyei G. Coord. Chem. Rev. 2003; 245: 85
- 24 Simándi LI. Barna T. Argay G. Simándi TL. Inorg. Chem. 1995; 34: 6337
- 25 Wendt F. Näther C. Tuczek F. J. Biol. Inorg. Chem. 2016; 21: 777
- 26 Tsuruya S. Yanai S.-I. Masai M. Inorg. Chem. 1986; 25: 141
- 27 Anson CW. Ghosh S. Hammes-Schiffer S. Stahl SS. J. Am. Chem. Soc. 2016; 138: 4186
- 28 Huynh MT. Anson CW. Cavell AC. Stahl SS. Hammes-Schiffer S. J. Am. Chem. Soc. 2016; 138: 15903
- 29 Ohshiro Y. Itoh S. Kurokawa K. Kato J. Hirao T. Agawa T. Tetrahedron Lett. 1983; 24: 3465
- 30 Qin Y. Zhang L. Lv J. Luo S. Cheng J.-P. Org. Lett. 2015; 17: 1469
- 31 Anthony C. Biochem. J. 1996; 320: 697
- 32 Ohshiro Y. Itoh S. Kurokawa K. Kato J. Hirao T. Agawa T. Tetrahedron Lett. 1983; 24: 3465
- 33 Itoh S. Kawakami H. Fukuzumi S. J. Am. Chem. Soc. 1997; 119: 439
- 34 Hirao T. Fukuhara S. J. Org. Chem. 1998; 63: 7534
- 35a Hirao T. Higuchi M. Ikeda I. Ohshiro Y. J. Chem. Soc., Chem. Commun. 1993; 194
- 35b Higuchi M. Ikeda I. Hirao T. J. Org. Chem. 1997; 62: 1072
- 35c Hirao T. Fukuhara S. J. Org. Chem. 1998; 63: 7534
- 35d Saio D. Amaya T. Hirao T. Adv. Synth. Catal. 2010; 352: 2177
- 36 Marmisollé WA. Inés Florit M. Posadas D. J. Electroanal. Chem. 2013; 707: 43
- 37 Shimizu S. Saitoh T. Uzawa M. Yuasa M. Yano K. Maruyama T. Watanabe K. Synth. Met. 1997; 85: 1337
- 38 Saio D. Amaya T. Hirao T. Adv. Synth. Catal. 2010; 352: 2177
- 39 Organic Redox Systems, Synthesis, Properties and Applications . Nishinaga T. John Wiley and Sons; Chichester: 2016
- 40 Broggi J. Terme T. Vanelle P. Angew. Chem. Int. Ed. 2014; 53: 384 ; Angew. Chem. 2014, 126, 392
- 42 Merz V. Weith W. Ber. Dtsch. Chem. Ges. 1873; 6: 1511
- 43 Amthor S. Noller B. Lambert C. Chem. Phys. 2005; 316: 141
- 44 Wudl F. Wobschall D. Hufnagel EJ. J. Am. Chem. Soc. 1972; 94: 670
- 45 Ferraris J. Cowan DO. Walatka VJr. Perlstein JH. J. Am. Chem. Soc. 1973; 95: 948
- 46 Hasegawa M. Daigoku K. Hashimoto K. Nishikawa H. Iyoda M. Bull. Chem. Soc. Jpn. 2012; 85: 51
- 47 Pruett RL. Barr JT. Rapp KE. Bahner CT. Gibson JD. Lafferty RH. J. Am. Chem. Soc. 1950; 72: 3646
- 48 Wanzlick H.-W. Schikora E. Angew. Chem. 1960; 72: 494
- 49 Wiberg N. Angew. Chem., Int. Ed. Engl. 1968; 7: 766 ; Angew. Chem. 1968, 80, 466
- 50 Taton TA. Chen PA. Angew. Chem., Int. Ed. Engl. 1996; 35: 1011 ; Angew. Chem. 1996, 108, 1098
- 51 Murphy JA. Zhou SZ. Thomson DW. Schoenebeck F. Mahesh M. Park SR. Tuttle T. Berlouis LE. A. Angew. Chem. Int. Ed. 2007; 46: 5178 ; Angew. Chem. 2007, 119, 5270
- 52 Doni E. Murphy JA. Chem. Commun. 2014; 50: 6073
- 53 Hahn F. Jahnke M. Angew. Chem. Int. Ed. 2008; 47: 3122 ; Angew. Chem. 2008, 120, 3166
- 54 Ames JR. Houghtaling MA. Terrian DL. Mitchell TP. Can. J. Chem. 1997; 75: 28
- 55 Porter WW. Vaid TP. Rheingold AJ. J. Am. Chem. Soc. 2005; 127: 16559
- 56 Han Z. Vaid TP. Rheingold AL. J. Org. Chem. 2008; 73: 445
- 57a Murphy JA. Garnier J. Park SR. Schoenebeck F. Zhou S.-Z. Turner AT. Org. Lett. 2008; 10: 1227
- 57b Garnier J. Murphy JA. Zhou S.-Z. Turner AT. Synlett 2008; 2127
- 58 Cahard E. Schoenebeck F. Garnier J. Cutulic SP. Y. Zhou S. Murphy JA. Angew. Chem. Int. Ed. 2012; 51: 3673 ; Angew. Chem. 2012, 124, 3733
- 59 Hanson SS. Doni E. Traboulsee KT. Coulthard G. Murphy JA. Dyker CA. Angew. Chem. Int. Ed. 2015; 54: 11236 ; Angew. Chem. 2015, 127, 11388
- 60 Broggi J. Rollet M. Clément J.-L. Canard G. Terme T. Gigmes D. Vanelle P. Angew. Chem. Int. Ed. 2016; 55: 5994
- 61 Tintori G. Nabokoff P. Buhaibeh R. Bergé-Lefranc D. Redon S. Broggi J. Vanelle P. Angew. Chem. Int. Ed. 2018; 57: 3148
- 62a Wurster C. Schobig E. Ber. Dtsch. Chem. Ges. 1879; 12: 1807
- 62b Wurster C. Ber. Dtsch. Chem. Ges. 1879; 12: 2071
- 62c Wurster C. Ber. Dtsch. Chem. Ges. 1887; 20: 808
- 63a Michaelis L. Hill ES. J. Am. Chem. Soc. 1933; 55: 1481
- 63b Michaelis L. Schubig MP. Granick S. J. Am. Chem. Soc. 1939; 61: 1981
- 64 See, for example: Hu K. Evans DH. J. Electroanal. Chem. 1997; 423: 29
- 65 Elbl K. Krieger C. Staab HA. Angew. Chem., Int. Ed. Engl. 1986; 25: 1023 ; Angew. Chem. 1986, 98, 1024
- 66 Backer HJ. Van der Baan S. Recl. Trav. Chim. Pays-Bas 1937; 56: 1175
- 67 Chance JM. Kahr B. Buda AB. Toscano JP. Mislow K. J. Org. Chem. 1988; 53: 3226
- 68 Speiser B. Würde M. Maichle-Mössner C. Chem. Eur. J. 1998; 4: 222
- 69 Speiser B. Würde M. Quintanilla MG. Electrochem. Commun. 2000; 2: 65
- 70 Eberle B. Hübner O. Ziesak A. Kaifer E. Himmel H.-J. Chem. Eur. J. 2015; 21: 8578
- 71 Adams CJ. da Costa RC. Edge R. Evans DH. Hood MF. J. Org. Chem. 2010; 75: 1168
- 72a Breslow R. Maslak P. Thomaides JS. J. Am. Chem. Soc. 1984; 106: 6453
- 72b Thomaides J. Maslak P. Breslow R. J. Am. Chem. Soc. 1988; 110: 3970
- 73a Miller JS. Dixon DA. Calabrese JC. Science 1988; 240: 1185
- 73b Miller JS. Dixon DA. Calabrese JC. Vazquez C. Krusic PJ. Ward MD. Wasserman E. Harlow RL. J. Am. Chem. Soc. 1990; 112: 381
- 74 Elbl-Weiser K. Krieger C. Staab HA. Angew. Chem., Int. Ed. Engl. 1990; 29: 21 ; Angew. Chem. 1990, 102, 183
- 75a Barth T. Krieger C. Neugebauer FA. Staab HA. Angew. Chem., Int. Ed. Engl. 1991; 30: 1028 ; Angew. Chem. 1991, 103, 1006
- 75b Barth T. Krieger G. Staab HA. Neugebauer FA. J. Chem. Soc., Chem. Commun. 1993; 1129
- 76 Kirsch A. Krieger C. Staab HA. Neugebauer FA. Tetrahedron Lett. 1994; 35: 8365
- 77a Bañuelos J. Martín V. Gómez-Durán CF. A. Córdoba IJ. A. Peña-Cabrera E. García-Moreno I. Costela Á. Pérez-Ojeda ME. Arbeloa T. Arbeloa ÍL. Chem. Eur. J. 2011; 17: 7261
- 77b Treich NR. Wimpenny JD. Kieffer IA. Heiden ZM. New J. Chem. 2017; 41: 14370
- 78 In some cases, the potentials versus the Fc+/Fc redox couple were calculated with the scale values from the following review: Connelly NG. Geiger WE. Chem. Rev. 1996; 96: 877
- 79 Bredereck H. Bredereck K. Chem. Ber. 1961; 94: 2278
- 80 Hornung J. Hübner O. Kaifer E. Himmel H.-J. RSC Adv. 2016; 6: 39323
- 81 Peters A. Kaifer E. Himmel H.-J. Eur. J. Org. Chem. 2008; 5907
- 82 Eberle B. Kaifer E. Himmel H.-J. Angew. Chem. Int. Ed. 2017; 56: 3360 ; Angew. Chem. 2017, 129, 3408
- 83 Lebkücher A. Wagner C. Hübner O. Kaifer E. Himmel H.-J. Inorg. Chem. 2014; 53: 9876
- 84 Hünig S. Balli H. Conrad H. Schott A. Justus Liebigs Ann. Chem. 1964; 676: 36
- 85 Villiers C. Thuéry P. Ephritikhine M. Chem. Commun. 2007; 2832
- 86 Reinmuth M. Neuhäuser C. Walter P. Enders M. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2011; 83
- 87 Herrmann H. Reinmuth M. Wiesner S. Hübner O. Kaifer E. Wadepohl H. Himmel H.-J. Eur. J. Inorg. Chem. 2015; 2345
- 88 Herrmann H. Kaifer E. Himmel H.-J. Chem. Eur. J. 2017; 23: 5520
- 89 Superbases for Organic Synthesis . Ishikawa T. John Wiley and Sons; Chichester: 2009
- 90 Oediger H. Möller F. Eiter K. Synthesis 1972; 591
- 91 Oediger H. Kabbe HJ. Möller F. Eiter K. Chem. Ber. 1966; 99: 2012
- 92 Oediger H. Möller F. Angew. Chem., Int. Ed. Engl. 1967; 6: 76 ; Angew. Chem. 1967, 79, 53
- 93 Coles MP. Chem. Commun. 2009; 3659
- 94 Schwesinger R. Angew. Chem., Int. Ed. Engl. 1987; 26: 1164 ; Angew. Chem. 1987, 99, 1209
- 95 Chamorro E. Escobar CA. Sienra R. Perez P. J. Phys. Chem. A 2005; 109: 10068
- 96a Schwesinger R. Schlemper H. Hasenfratz C. Willaredt J. Dambacher T. Breuer T. Ottaway C. Fletschinger M. Boele J. Fritz H. Putzas D. Rotter HW. Bordwell FG. Satish AV. Ji GZ. Peters E.-M. Peters K. von Schnering HG. Walz L. Liebigs Ann. 1996; 1055
- 96b Schwesinger R. Schlemper H. Angew. Chem., Int. Ed. Engl. 1987; 26: 1167 ; Angew. Chem. 1987, 99, 1212
- 97 Schwesinger R. Hasenfratz C. Schlemper H. Walz L. Peters E.-M. Peters K. von Schnering HG. Angew. Chem., Int. Ed. Engl. 1993; 32: 1361 ; Angew. Chem. 1993, 105, 1420
- 98 Schmidt H. Lensink C. Xi SK. Verkade JG. Z. Anorg. Allg. Chem. 1989; 578: 75
- 99 Tang J. Dopke J. Verkade JG. J. Am. Chem. Soc. 1993; 115: 5015
- 100 Raab V. Gauchenova E. Merkoulov A. Harms K. Sundermeyer J. Kovačević B. Maksić ZB. J. Am. Chem. Soc. 2005; 127: 15738
- 101 Lebkücher A. Rybina A. Herten D.-P. Hübner O. Wadepohl H. Kaifer E. Himmel H.-J. Z. Anorg. Allg. Chem. 2011; 637: 547
- 102 Alder RW. Bowman PS. Steele WR. S. Winterman DR. J. Chem. Soc., Chem. Commun. 1968; 723
- 103 Staab HA. Saupe T. Angew. Chem., Int. Ed. Engl. 1988; 27: 865 ; Angew. Chem. 1988, 100, 895
- 104 Alder RW. Chem. Rev. 1989; 89: 1215
- 105 Einspahr H. Robert J.-B. Marsh RE. Roberts JD. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1973; 29: 1611
- 106 Staab HA. Saupe T. Krieger C. Angew. Chem., Int. Ed. Engl. 1983; 22: 731 ; Angew. Chem. 1983, 95, 748
- 107 Saupe T. Krieger C. Staab HA. Angew. Chem., Int. Ed. Engl. 1986; 25: 451 ; Angew. Chem. 1986, 98, 460
- 108 See, for example: Kaljurand I. Kütt A. Sooväli L. Rodima T. Mäemets V. Leito I. Koppel IA. J. Org. Chem. 2005; 70: 1019
- 109 Strecker A. Justus Liebigs Ann. Chem. 1861; 118: 151
- 110 Yamada T. Liu X. Englert U. Yamane H. Dronskowski R. Chem. Eur. J. 2009; 15: 5651
- 111 Sawinski PK. Meven M. Englert U. Dronskowski R. Cryst. Growth Des. 2013; 13: 1730
- 112 Raczyńska ED. Cyrański M. Gutowski M. Rak J. Fal J.-F. Maria P.-C. Darowska M. Duczmal K. J. Phys. Org. Chem. 2003; 16: 91
- 113 Berlinck RG. S. Romminger S. Nat. Prod. Rep. 2016; 33: 456
- 114 Maksić ZB. Kovačević B. J. Chem. Soc., Perkin Trans. 2 1999; 2623
- 115 Kovačević B. Maksić ZB. Chem. Eur. J. 2002; 8: 1694
- 116 Antol I. Glasovac Z. Margetić D. Crespo-Otero R. Barbatti M. J. Phys. Chem. A 2016; 120: 7088
- 117 Foroughifar N. Leffek KT. Lee YG. Can. J. Chem. 1993; 71: 164
- 118a Hoffmann A. Börner J. Flörke U. Herres-Pawlis S. Inorg. Chim. Acta 2009; 362: 1185
- 118b Börner J. Flörke U. Huber K. Döring A. Kuckling D. Herres-Pawlis S. Chem. Eur. J. 2009; 15: 2362
- 118c Hoffmann A. Binder S. Jesser A. Haase R. Flörke U. Gnida M. Stagni MS. Meyer-Klaucke W. Lebsanft B. Grünig LE. Schneider S. Hashemi M. Goos A. Wetzel A. Rübhausen M. Herres-Pawlis S. Angew. Chem. Int. Ed. 2014; 53: 299 ; Angew. Chem. 2014, 126, 305
- 118d Rösener T. Bienemann O. Sigl K. Schopp N. Schnitter F. Flörke U. Hoffmann A. Döring A. Kuckling D. Herres-Pawlis S. Chem. Eur. J. 2016; 22: 13550
- 119 Kovačević B. Maksić ZB. Org. Lett. 2001; 3: 1523
- 120 Glasovac Z. Eckert-Maksić M. Maksić ZB. New J. Chem. 2009; 33: 588
- 121 Kawahata M. Yamaguchi K. Ito T. Ishikawa T. Acta Crystallogr., Sect. E: Struct. Rep. Online 2006; 62: o3301
- 122 Kovačević B. Maksić ZB. Vianello R. Primorac M. New J. Chem. 2002; 26: 1329
- 123a Peters A. Wild U. Hübner O. Kaifer E. Himmel H.-J. Chem. Eur. J. 2008; 14: 7813
- 123b Reinmuth M. Wild U. Kaifer E. Enders M. Wadepohl H. Himmel H.-J. Eur. J. Inorg. Chem. 2009; 4795
- 124 Roquette P. Maronna A. Peters A. Kaifer E. Himmel H.-J. Hauf C. Herz V. Scheidt E.-W. Scherer W. Chem. Eur. J. 2010; 16: 1336
- 125 Suzuki N. Kishimoto K. Yamazaki K. Kumamoto T. Ishikawa T. Margetić D. Synlett 2013; 24: 2510
- 126 Raab V. Kipke J. Gschwind RM. Sundermeyer J. Chem. Eur. J. 2002; 8: 1682
- 127a Vitske V. König C. Kaifer E. Hübner O. Himmel H.-J. Eur. J. Inorg. Chem. 2010; 115
- 127b Vitske V. Roquette P. Leingang S. Adam C. Kaifer E. Wadepohl H. Himmel H.-J. Eur. J. Inorg. Chem. 2011; 1593
- 128 Eberle B. Herrmann H. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2013; 3671
- 129 Peters A. Herrmann H. Magg M. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2012; 1620
- 130 Connelly NG. Geiger WE. Chem. Rev. 1996; 96: 877
- 131 Stang S. Lebkücher A. Walter P. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2012; 4833
- 132a Emeljanenko D. Peters A. Vitske V. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2010; 4783
- 132b Wild U. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2011; 4220
- 133 Wild U. Neuhäuser C. Wiesner S. Kaifer E. Wadepohl H. Himmel H.-J. Chem. Eur. J. 2014; 20: 5914
- 134 Wild U. Kaifer E. Wadepohl H. Himmel H.-J. Eur. J. Inorg. Chem. 2015; 4848
- 135 Ziesak A. Wesp T. Hübner O. Kaifer E. Wadepohl H. Himmel H.-J. Dalton Trans. 2015; 44: 19111
- 136 Wiesner S. Ziesak A. Reinmuth M. Walter P. Kaifer E. Wadepohl H. Himmel H.-J. Eur. J. Inorg. Chem. 2013; 163
- 137 Roquette P. Maronna A. Peters A. Kaifer E. Himmel H.-J. Hauf C. Herz V. Scheidt E.-W. Scherer W. Chem. Eur. J. 2010; 16: 1336
- 138 Himmel H.-J. Z. Anorg. Allg. Chem. 2013; 639: 1940
- 139 Wiesner S. Wagner A. Kaifer E. Himmel H.-J. Chem. Eur. J. 2016; 22: 10438
- 140 Wiesner S. Wagner A. Kaifer E. Himmel H.-J. Dalton Trans. 2016; 45: 15828
- 141a Schrempp DF. Leingang S. Schnurr M. Kaifer E. Wadepohl H. Himmel H.-J. Chem. Eur. J. 2017; 23: 13607
- 141b Schrempp DF. Leingang S. Schnurr M. Kaifer E. Wadepohl H. Himmel H.-J. Chem. Eur. J. 2016; 22: 16187
- 142a Emeljanenko D. Peters A. Wagner N. Beck J. Kaifer E. Himmel H.-J. Eur. J. Inorg. Chem. 2010; 1839
- 142b Trumm C. Stang S. Eberle B. Kaifer E. Wagner N. Beck J. Bredow T. Meyerbröker N. Zharnikov M. Hübner O. Himmel H.-J. Eur. J. Inorg. Chem. 2012; 3156
- 143 Wiesner S. Wagner A. Hübner O. Kaifer E. Himmel H.-J. Chem. Eur. J. 2015; 21: 16494
- 144 Trumm C. Hübner O. Walter P. Leingang S. Wild U. Kaifer E. Eberle B. Himmel H.-J. Eur. J. Inorg. Chem. 2014; 6039
- 145 Eberle B. Damjanovic M. Enders M. Leingang S. Pfisterer J. Krämer C. Hübner O. Kaifer E. Himmel H.-J. Inorg. Chem. 2016; 55: 1683
- 146 Herrmann H. Ziesak A. Wild U. Leingang S. Schrempp D. Wagner N. Beck J. Kaifer E. Wadepohl H. Himmel H.-J. ChemPhysChem 2014; 15: 351
- 147 Vitske V. Herrmann H. Enders M. Kaifer E. Himmel H.-J. Chem. Eur. J. 2012; 18: 14108
- 148 Schneider S. Brohmann M. Lorenz R. Hofstetter YJ. Rother M. Sauter E. Zharnikov M. Vaynzof Y. Himmel H.-J. Zaumseil J. ACS Nano 2018;
- 149a Stang S. Kaifer E. Himmel H.-J. Chem. Eur. J. 2014; 20: 5288
- 149b Wiesner S. Walter P. Wagner A. Kaifer E. Himmel H.-J. Eur. J. Org. Chem. 2016; 5045
- 150 Wild U. Federle S. Wagner A. Kaifer E. Himmel H.-J. Chem. Eur. J. 2016; 22: 11971
- 151 Kieffer IA. Allen RJ. Fernandez JL. Deobald JL. Thompson BL. Wimpenny JD. Heiden ZM. Angew. Chem. Int. Ed. 2018; 57: 3377 ; Angew. Chem. 2018, 130, 3435
- 152 Wild U. Schön F. Himmel H.-J. Angew. Chem. Int. Ed. 2017; 56: 16410 ; Angew. Chem. 2017, 129, 16630
- 153 Wild, U.; Kaifer, E.; Himmel, H.-J. unpublished results.