Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C60 Derivatives

Ning Lou; Olga A. Kraevaya; Pavel A. Troshin; Liangbing Gan

doi:10.1055/s-0037-1610220

Synthesis, Table of Contents

Synthesis 2018; 50(21): 4283-4289
DOI: 10.1055/s-0037-1610220

paper

Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C₆₀ Derivatives

Ning Lou

^aBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China Email: gan@pku.edu.cn

,

Olga A. Kraevaya

^bInstitute for Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow Region, 142432, Russian Federation Email: troshin2003@inbox.ru

,

Pavel A. Troshin*

^bInstitute for Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow Region, 142432, Russian Federation Email: troshin2003@inbox.ru

^cSkolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russian Federation

,

Liangbing Gan*

^aBeijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China Email: gan@pku.edu.cn

^dState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

Unlike the facile addition of aliphatic amines to fullerenes, heteroaromatic compounds with NH group do not react directly with pristine fullerenes. The present work reports the preparation of several cyclopentadienyl type [60]fullerene derivatives with pyrazole and pyrrole addends through replacement reactions of C₆₀Cl₆ in the presence of tetrabutylammonium bromide. The method has also been applied for the synthesis of aniline and methoxyamine [60]fullerene cyclopentadienyl type adducts. Radical species were involved in the reaction mechanism.

Key words

fullerene - amination - pyrrole - substituent effect - nucleophilic aromatic substitution

Full Text

References

References

1a Hirsch A. Brettreich M. Fullerenes: Chemistry and Reactions . Wiley-VCH; Weinheim: 2005
1b Miller GP. C. R. Chim. 2006; 9: 952

2a Kuwashima S. Kubota M. Kushida K. Ishida T. Ohashi M. Nogami T. Tetrahedron Lett. 1994; 35: 4371
2b Wang NX. Li JS. Zhu DB. Chan TH. Tetrahedron Lett. 1995; 36: 431
2c Zhang X. Gan LB. Huang SH. Shi YR. J. Org. Chem. 2004; 69: 5800
2d Tsuruoka R. Nagamachi T. Murakami Y. Komatsu M. Minakata S. J. Org. Chem. 2009; 74: 1691
2e Yang H.-T. Liang X.-C. Wang Y.-H. Yang Y. Sun X.-Q. Miao C.-B. J. Org. Chem. 2013; 78: 11992
2f Miao C.-B. Lu X.-W. Wu P. Li JX. Ren W.-L. Xing M.-L. Sun X.-Q. Yang H.-T. J. Org. Chem. 2013; 78: 12257
2g He C.-L. Liu R. Li D.-D. Zhu S.-E. Wang G.-W. Org. Lett. 2013; 15: 1532
2h Yang H.-T. Liang X.-C. Wang Y.-H. Yang Y. Sun X.-Q. Miao C.-B. Org. Lett. 2013; 15: 4650

3 Maggini M. Scorrano G. Prato M. J. Am. Chem. Soc. 1993; 115: 9798

4a Schick G. Kampe K.-D. Hirsch A. J. Chem. Soc., Chem. Commun. 1995; 2023
4b Isobe H. Ohbayashi A. Sawamura M. Nakamura E. J. Am. Chem. Soc. 2000; 122: 2669
4c Isobe H. Tomita N. Nakamura E. Org. Lett. 2000; 2: 3663
4d Isobe H. Tanaka T. Nakanishi W. Lemiègre L. Nakamura E. J. Org. Chem. 2005; 70: 4826
4e Troshina OA. Troshin PA. Peregudov AS. Kozlovski VI. Lyubovskaya RN. Chem. Eur. J. 2006; 12: 5569
4f Lemiègre L. Tanaka T. Nanao T. Isobe H. Nakamura E. Chem. Lett. 2007; 36: 20
4g Li YB. Gan LB. J. Org. Chem. 2014; 79: 8912
4h Li YB. Lou N. Gan LB. Org. Lett. 2015; 17: 524
4i Liang SS. Xu L. Gan LB. Eur. J. Org. Chem. 2016; 3070
4j Li YB. Xu D. Gan LB. Angew. Chem. Int. Ed. 2016; 55: 2483

5a Lawson GE. Kitaygorodskiy A. Ma B. Bunker CE. Sun Y.-P. J. Chem. Soc., Chem. Commun. 1995; 2225
5b Liou K.-F. Cheng C.-H. Chem. Commun. 1996; 1423
5c Gan LB. Jiang JF. Zhang W. Su Y. Shi YR. Huang CH. Pan JQ. Lu MJ. Wu Y. J. Org. Chem. 1998; 63: 4240
5d Bernstein R. Foote CS. J. Phys. Chem. A 1999; 103: 7244
5e Lawson GE. Kitaygorodskiy A. Sun Y.-P. J. Org. Chem. 1999; 64: 5913
5f Nakamura Y. Suzuki M. Okawa K. Konno T. Nishimura J. J. Org. Chem. 2005; 70: 8472
5g Wang G.-W. Chen XP. Cheng X. Chem. Eur. J. 2006; 12: 7246
5h Troshina OA. Troshin PA. Peregudov AS. Lyubovskaya RN. Mendeleev Commun. 2007; 17: 113
5i Miyake Y. Ashida Y. Nakajima K. Nishibayashi Y. Chem. Eur. J. 2014; 20: 6120
5j Lim SH. Yi J. Moon GM. Ra CS. Nahm K. Cho DW. Kim K. Hyung TG. Yoon UC. Lee GY. Kim S. Kim J. Mariano PS. J. Org. Chem. 2014; 79: 6946

6 Lu X.-W. Xing M.-L. Miao C.-B. Li J.-X. Sun X.-Q. Yang H.-T. Org. Biomol. Chem. 2015; 13: 8405

7a Darwish AD. Avent AG. Kroto HW. Taylor R. Walton DR. M. J. Chem. Soc., Perkin Trans. 2 1999; 1983
7b Jia ZS. Zhang X. Zhang GH. Huang SH. Fang H. Hu XQ. Li YL. Gan LB. Zhang SW. Zhu DB. Chem. Asian J. 2007; 2: 290

8a Avent AG. Birkett PR. Crane JD. Darwish AD. Langley GJ. Kroto HW. Taylor R. Walton DR. M. J. Chem. Soc., Chem. Commun. 1994; 1463
8b Troshina OA. Troshin PA. Peregudov AS. Kozlovskiy VI. Balzarini J. Lyubovskaya RN. Org. Biomol. Chem. 2007; 5: 2783
8c Kornev AB. Peregudov AS. Martynenko VM. Balzarini J. Hoorelbeke B. Troshin PA. Chem. Commun. 2011; 47: 8298

9 Matsuo Y. Nakamura E. Chem. Rev. 2008; 108: 3016

10a Birkett PR. Avent AG. Darwish AD. Kroto HW. Taylor R. Walton DR. M. J. Chem. Soc., Chem. Commun. 1993; 1230
10b Troshin PA. Popkov O. Lubovskaya RN. Fullerenes, Nanotubes, Carbon Nanostruct. 2003; 11: 163

11a Birkett PB. Avent AG. Darwish AD. Hahn I. Kroto HW. Langley GJ. O’Loughlin J. Taylor T. Walton DR. M. J. Chem. Soc., Perkin Trans. 2 1997; 1121
11b Avent AG. Birkett PR. Darwish AD. Houlton S. Taylor R. Thomson KS. T. Wei X.-W. J. Chem. Soc., Perkin Trans. 2 2001; 782
11c Al-Matar H. Abdul-Sada AK. Avent AG. Fowler PW. Hitchcock PB. Rogers KM. Taylor R. J. Chem. Soc., Perkin Trans. 2 2002; 53

12a Kornev AB. Khakina EA. Troyanov SI. Kushch AA. Deryabin DG. Peregudov AS. Vasilchenko A. Martynenko VM. Troshin PA. Chem. Commun. 2012; 48: 5461
12b Khakina EA. Yurkova A. Peregudov AS. Troyanov SI. Trush V. Vovk AI. Mumyatov AV. Martynenko VM. Balzarini J. Troshin PA. Chem. Commun. 2012; 48: 7158
12c Yurkova AA. Khakina EA. Troyanov SI. Chernyak A. Shmygleva L. Peregudov AS. Martynenko VM. Dobrovolskiy YA. Troshin PA. Chem. Commun. 2012; 48: 8916
12d Khakina EA. Kraevaya OA. Popova ML. Peregudov AS. Troyanov SI. Chernyak AV. Martynenko VM. Kulikov AV. Schols D. Troshin PA. Org. Biomol. Chem. 2017; 15: 773

13a Deng LL. Xie SL. Yuan C. Liu RF. Fen J. Sun LC. Lu X. Xie SY. Huang RB. Zheng LS. Sol. Energy Mater. Sol. Cells 2013; 111: 193
13b Yan P. Tian C-B. Gao C-L. Zhang QY. Zhan Z-P. Xie S-Y. Lin M. Huang R-B. Zheng L-S. Tetrahedron 2014; 70: 6776

14a Lou N. Li YB. Cui CX. Liu YJ. Gan LB. Org. Lett. 2016; 18: 2236
14b Lou N. Gan LB. Can. J. Chem. 2017; 95: 292

15 Desyatkin VG. Beletskaya IP. Synthesis 2017; 49: 4327
16 Hu XQ. Jiang ZP. Jia ZS. Huang SH. Yang XB. Li YL. Gan LB. Zhang SW. Zhu DB. Chem. Eur. J. 2007; 13: 1129

17a Sawamura M. Kawai K. Matsuo Y. Kanie K. Kato T. Nakamura E. Nature 2002; 419: 702
17b Neubauer R. Heinemann FW. Hampel F. Rubin Y. Hirsch A. Angew. Chem. Int. Ed. 2012; 51: 11722
17c Xu D. Li YB. Lou N. Gan LB. Org. Chem. Front. 2017; 4: 750

18a Khakina EA. Yamilova OR. Novikov AV. Godovikov IA. Peregudov AS. Troshin PA. Tetrahedron Lett. 2016; 57: 5570
18b Khakina EA. Peregudov AS. Yurkova AA. Piven NP. Shestakov AF. Troshin PA. Tetrahedron Lett. 2016; 57: 1215
18c Khakina EA. Troshin PA. Russ. Chem. Rev. 2017; 86: 805

19 CCDC 1843599 contains 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/getstructures.

Supplementary Material

Supporting Information