Aminocyclopropenium Ions: Synthesis, Properties, and Applications

Jeffrey S. Bandar; Tristan H. Lambert

doi:10.1055/s-0033-1338516

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(18): 2485-2498
DOI: 10.1055/s-0033-1338516

review

Aminocyclopropenium Ions: Synthesis, Properties, and Applications

Jeffrey S. Bandar

Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA Fax: +1(212)9321289 eMail: tl2240@columbia.edu

,

Tristan H. Lambert*

Columbia University, Department of Chemistry, 3000 Broadway, New York, NY 10027, USA Fax: +1(212)9321289 eMail: tl2240@columbia.edu

› Institutsangaben

Abstract

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Abstract

This review covers the preparation, physical properties, and applications of cyclopropenium ions bearing one, two, or three amino substituents. It provides a description of the most reliable methods to access these unique structures as well as a discussion of the reactivity profiles of the common subtypes.

1 Introduction

2 Preparation

3 Properties

3.1 Stability

3.2 Redox Behavior

3.3 Ion Pair Strain

4 Reactions

5 Applications

5.1 Ionic Liquids

5.2 Metal Complexes

5.2.1 TDAC π-Complexes

5.2.2 BDAC σ-Complexes

5.2.3 Cyclopropenimine Ligands

5.2.4 BDAC–Phosphorus Ligands

5.3 Brønsted Bases

6 Conclusion

Key words

cyclopropenium ions - aromaticity - cyclopropenimines - ionic liquids - ligands

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Referenzen

References
1 Breslow R. J. Am. Chem. Soc. 1957; 79: 5318

For selected reviews, see:

2a Komatsu K, Kitagawa T. Chem. Rev. 2003; 103: 1371
2b Komatsu K, Yoshida Z In Houben–Weyl Methods of Organic Chemistry . Vol. E17d. de Meijere A. Georg Thieme; Stuttgart: 1996: 3079-3192
2c Khimii U. Russ. Chem. Rev. 1967; 36: 557
2d Krivun SV. Russ. Chem. Rev. 1974; 43: 835
2e Yoshida Z.-i. Top. Curr. Chem. 1973; 40: 47

3 Yoshida Z.-i, Tawara Y. J. Am. Chem. Soc. 1971; 93: 2573
4 Tetrachlorocyclopropene is available from Sigma-Aldrich, product no. 145947.

5a Tobey SW, West R. Tetrahedron Lett. 1963; 1179
5b Tobey SW, West R. J. Am. Chem. Soc. 1966; 88: 2481
5c For a key modification, see: Sepiol J, Soulen RL. J. Org. Chem. 1975; 40: 3791

6 Wilcox C, Breslow R. Tetrahedron Lett. 1980; 21: 3241
7 Bandar JS, Lambert TH. J. Am. Chem. Soc. 2012; 134: 5552
8 Taylor MJ, Surman PW. J, Clark GR. J. Chem. Soc., Chem. Commun. 1994; 2517
9 Weiss R, Schloter K. Tetrahedron Lett. 1975; 3491
10 Weiss R. Tetrahedron Lett. 1979; 3295
11 Weiss R, Hertel M. J. Chem. Soc., Chem. Commun. 1980; 223
12 Eggerding D, West R. J. Am. Chem. Soc. 1976; 98: 3641
13 Wu MT, Taub D, Patchett AA. Tetrahedron Lett. 1976; 2405

For reviews of cyclopropene chemistry, see:

14a Zhu Z.-B, Wei Y, Shi M. Chem. Soc. Rev. 2011; 40: 5534
14b Rubin M, Rubina M, Gevorgyan V. Chem. Rev. 2007; 107: 3117

15 Yoshida Z.-i, Konishi H, Miura Y, Ogoshi H. Tetrahedron Lett. 1977; 4319
16 Certainly for their size. Structures with more extended π-systems are known to result in higher stabilities; for example, see: Laursen BW, Sørensen TJ. J. Org. Chem. 2009; 74: 3183
17 Kerber RC, Hsu C.-M. J. Am. Chem. Soc. 1973; 95: 3239
18 Yoshida Z.-i, Tawara Y, Hirota S, Ogoshi H. Bull. Chem. Soc. Jpn. 1974; 47: 797
19 Gerson F, Plattner G, Yoshida Z. Mol. Phys. 1971; 21: 1027
20 Johnson RW. Tetrahedron Lett. 1976; 589
21 Weiss R, Brenner T, Hampel F, Wolski A. Angew. Chem., Int. Ed. Engl. 1995; 34: 439

22a Butchard JR, Curnow OJ, Garrett DJ, Maclagan RG. A. R. Angew. Chem. Int. Ed. 2006; 45: 7550
22b See also: Butchard JR, Curnow OJ, Garrett DJ, Maclagan RG. A. R, Libowitzky E, Piccoli PM. B, Schultz AJ. Dalton Trans. 2012; 41: 11765

23 Weiss R, Rechinger M, Hampel F, Wolski A. Angew. Chem., Int. Ed. Engl. 1995; 34: 441
24 Weiss R, Schwab O, Hampel F. Chem. Eur. J. 1999; 5: 968
25 Yoshida Z, Konishi H, Tawara Y, Nishikawa K, Ogoshi H. Tetrahedron Lett. 1973; 2619
26 Breslow R, Eicher T, Krebs A, Peterson RA, Posner J. J. Am. Chem. Soc. 1965; 87: 1320
27 Viehe HG, Delavarenne SY. Chem. Ber. 1970; 103: 1209
28 Plechkova NV, Seddon KR. Chem. Soc. Rev. 2008; 37: 123

29a Curnow OJ, MacFarlane DR, Walst KJ. Chem. Commun. 2011; 47: 10248
29b See also: Curnow OJ, Holmes MT, Ratten LC, Walst KJ, Yunis R. RSC Adv. 2012; 2: 10794

30 Reutiv OA, Kurts AL. Russ. Chem. Rev. 1977; 46: 1040
31 Badri M, Brunet J.-J. Tetrahedron Lett. 1992; 33: 4435

32a Harris D, Gray HB. Inorg. Chem. 1974; 13: 2250
32b Cowman CD, Thibeault JC, Ziolo RF, Gray HB. J. Am. Chem. Soc. 1976; 98: 3209

For reviews on NHC ligands, see:

33a N-Heterocyclic Carbenes in Synthesis . Nolan SP. Wiley-VCH; Weinheim: 2006
33b N-Heterocyclic Carbenes in Transition Metal Catalysis. In Topics in Organometallic Chemistry. Vol. 21. Glorius F. Springer; Berlin: 2007
33c Kühl O. Functionalised N-Heterocyclic Carbene Complexes . John Wiley & Sons Ltd; Chichester: 2010
33d N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Cazin CS. J. Springer; Heidelberg: 2011

34 Lavallo V, Canac Y, Donnadieu B, Schoeller WW, Bertrand G. Science 2006; 312: 722
35 Lavallo V, Ishida Y, Donnadieu B, Bertrand G. Angew. Chem. Int. Ed. 2006; 45: 6652
36 Kuchenbeiser G, Soleilhavoup M, Donnadieu B, Bertrand G. Chem. Asian J. 2009; 4: 1745
37 Holschumacher D, Hrib CG, Jones PG, Tamm M. Chem. Commun. 2007; 3661

38a Melaimi M, Soleilhavoup M, Bertrand G. Angew. Chem. Int. Ed. 2010; 49: 8810
38b See also ref. 2a

For additions to non-metals, see:

39a Yoshida Z, Konishi H, Sawada S, Ogoshi H. J. Chem. Soc., Chem. Commun. 1977; 850
39b Weiss R, Priesner C, Wolf H. Angew. Chem., Int. Ed. Engl. 1978; 17: 446
39c Weiss R, Hertel M, Wolf H. Angew. Chem., Int. Ed. Engl. 1979; 18: 473

For additions to metals, see:

40a Gompper R, Bartmann E. Angew. Chem., Int. Ed. Engl. 1978; 17: 456
40b Weiss R, Priesner C. Angew. Chem., Int. Ed. Engl. 1978; 17: 457
40c Konishi H, Matsumoto S, Kamitori Y, Ogoshi H, Yoshida Z. Chem. Lett. 1978; 241
40d Gompper R, Wolf U. Liebigs Ann. Chem. 1979; 1406
40e Weiss R, Wolf H. Chem. Ber. 1980; 113: 1746
40f Yoshida Z. Pure Appl. Chem. 1982; 54: 1059
40g Miki S, Ohno T, Iwasaki H, Yoshida Z. J. Phys. Org. Chem. 1988; 1: 333
40h Tamm M, Grzegorzewski A, Hahn FE. J. Organomet. Chem. 1995; 501: 309
40i Schumann H, Glanz M, Girgsdies F, Hahn FE, Tamm M, Grzegorzewski A. Angew. Chem., Int. Ed. Engl. 1997; 36: 2232

41 Kuchenbeiser G, Donnadieu B, Bertrand G. J. Organomet. Chem. 2008; 693: 899
42 Lavallo V, El-Batta A, Bertrand G, Grubbs RH. Angew. Chem. Int. Ed. 2011; 50: 268
43 Miki S, Ohno T, Iwasaki H, Maeda Y, Yoshida Z. Tetrahedron 1988; 44: 55
44 Malik HA, Sormunen GJ, Montgomery J. J. Am. Chem. Soc. 2010; 132: 6304
45 Bruns H, Patil M, Carreras J, Vazquez A, Thiel W, Goddard R, Alcarazo M. Angew. Chem. Int. Ed. 2010; 49: 3680
46 Petuškova J, Bruns H, Alcarazo M. Angew. Chem. Int. Ed. 2011; 50: 3799

During the preparation of this manuscript Alcarazo and co-workers reported the synthesis and characterization of cyclopropenylidene-stabilized N-, S-, Se-, and Te-centered cations:

47a Kozma Á, Gopakumar G, Farès C, Thiel W, Alcarazo M. Chem. Eur. J. 2013; 19: 3542
47b Kozma Á, Petruškova J, Lehmann CW, Alcarazo M. Chem. Commun. 2013; 49: 4145

48 Petuškova J, Patil M, Holle S, Lehmann CW, Thiel W, Alcarazo M. J. Am. Chem. Soc. 2011; 133: 20758
49 Carreras J, Patil M, Thiel W, Alcarazo M. J. Am. Chem. Soc. 2012; 134: 16753
50 Tran Huy NH, Donnadieu B, Bertrand G, Mathey F. Chem. Asian J. 2009; 4: 1225
51 Tran Huy NH, Donnadieu B, Bertrand G, Mathey F. Organometallics 2010; 29: 1302

52a Maksić ZB, Kovačević B. J. Phys. Chem. A 1999; 103: 6678
52b Kovačević B, Maksić ZB, Vianello R. J. Chem. Soc., Perkin Trans. 2 2001; 886
52c Maksić ZB, Vianello R. J. Phys. Chem. A 2002; 106: 419
52d Barić D, Maksić ZB. J. Phys. Org. Chem. 2003; 16: 753
52e Gattin Z, Kovačević B, Maksić ZB. Eur. J. Org. Chem. 2005; 3206

For examples of the synthesis of cyclopropenimines, see:

53a Paquette LA, Barton TJ, Horton N. Tetrahedron Lett. 1967; 5039
53b Eicher T, Graf R, Konzmann H. Synthesis 1987; 887
53c Eicher T, Lerch D. Tetrahedron Lett. 1980; 21: 3751
53d Krebs A, Günter A, Versteylen S, Schulz S. Tetrahedron Lett. 1984; 25: 2333
53e Weiss R, Hertel M. J. Chem. Soc., Chem. Commun. 1980; 223
53f Pilli RA, Rodrigues JA. R, Kascheres A. J. Org. Chem. 1983; 48: 1084

54 Kaljurand I, Kütt A, Sooväli L, Rodima T, Mäemets V, Leito I, Koppel IA. J. Org. Chem. 2005; 70: 1019
55 Superbases for Organic Synthesis: Guanidines, Amidines, Phosphazenes and Related Organocatalysts. Ishikawa T. John Wiley & Sons; Chichester: 2009

56a Ishikawa T, Araki Y, Kumamoto T, Seki H, Fukuda K, Isobe T. Chem. Commun. 2001; 245
56b The product 115 was obtained as the opposite antipode.

57 During the preparation of this manuscript we reported on the chiral cyclopropenimide-catalyzed Mannich reaction between glycine imines and N-Boc aldimines: Bandar JS, Lambert TH. J. Am. Chem. Soc. 2013; 135: 11799