Reactivity and Synthetic Applications of α‐Functionalized Oxime Acetates: Divergent Access to Fulleropyrrolidines and Mono‐ and Disubstituted 1‐Fulleropyrrolines via Copper‐Catalyzed Redox‐Neutral N‐Heteroannulation with [60]Fullerene

作者: Tong-Xin Liu , Shaoshuai Hua , Nana Ma , Pengling Zhang , Jingjing Bi

DOI: 10.1002/ADSC.201701091

关键词:

摘要: The unique reactivity and synthetic applications of oxime acetate derivatives with N, O S-substituent at the α-position are disclosed for first time, which leads to 2-substituted fulleropyrrolidines mono- disubstituted 1-fulleropyrrolines via copper-catalyzed redox-neutral N-heteroannulation reactions C60. This transformation is operationally simple has a broad substrate scope good functional-group tolerance. Theoretical calculations level B3LYP/6-31G(d) were performed elucidate chemoselectivity reaction.

参考文章(68)
Bo Jin, Juan Shen, Rufang Peng, Congdi Chen, Shijin Chu, Reactions of [60]Fullerene with Halides and Amino Acids to Synthesize Fulleropyrrolidines European Journal of Organic Chemistry. ,vol. 2014, pp. 6252- 6262 ,(2014) , 10.1002/EJOC.201402655
A. V. Mumyatov, F. A. Prudnov, L. N. Inasaridze, O. A. Mukhacheva, P. A. Troshin, High LUMO energy pyrrolidinofullerenes as promising electron-acceptor materials for organic solar cells Journal of Materials Chemistry C. ,vol. 3, pp. 11612- 11617 ,(2015) , 10.1039/C5TC02509E
Liangbing Gan, Dazhi Yang, Qianyan Zhang, Huan Huang, Preparation of Open‐Cage Fullerenes and Incorporation of Small Molecules Through Their Orifices Advanced Materials. ,vol. 22, pp. 1498- 1507 ,(2010) , 10.1002/ADMA.200903705
Pavel A. Troshin, Alexander S. Peregudov, David Mühlbacher, Rimma N. Lyubovskaya, An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands European Journal of Organic Chemistry. ,vol. 2005, pp. 3064- 3074 ,(2005) , 10.1002/EJOC.200500048
E Espinosa, E Molins, C Lecomte, Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities Chemical Physics Letters. ,vol. 285, pp. 170- 173 ,(1998) , 10.1016/S0009-2614(98)00036-0
Liangbing Gan, Dejian Zhou, Chuping Luo, Haisong Tan, Chunhui Huang, Mujian Lü, Jinqi Pan, Yi Wu, Synthesis of Fullerene Amino Acid Derivatives by Direct Interaction of Amino Acid Ester with C60 Journal of Organic Chemistry. ,vol. 61, pp. 1954- 1961 ,(1996) , 10.1021/JO951933U
Salvatore Filippone, Enrique E. Maroto, Ángel Martín-Domenech, Margarita Suarez, Nazario Martín, An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions Nature Chemistry. ,vol. 1, pp. 578- 582 ,(2009) , 10.1038/NCHEM.361
Fausto Puntoriero, Paola Ceroni, Vincenzo Balzani, Giacomo Bergamini, Fritz Vögtle, Photoswitchable Dendritic Hosts: A Dendrimer with Peripheral Azobenzene Groups Journal of the American Chemical Society. ,vol. 129, pp. 10714- 10719 ,(2007) , 10.1021/JA070636R
Paul A. Liddell, Gerdenis Kodis, Ana L. Moore, Thomas A. Moore, Devens Gust, Photonic switching of photoinduced electron transfer in a dithienylethene-porphyrin-fullerene triad molecule. Journal of the American Chemical Society. ,vol. 124, pp. 7668- 7669 ,(2002) , 10.1021/JA026327C