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Citation: HU Jin-Chuan, FENG Wen, LI Xiang-Hui, YANG Liu-Qing, YUAN Li-Hua, HE Lan, NG Bing. One-Pot Formation of Aromatic Oli amide Macrocycles and the Corresponding Mechanism[J]. Acta Physico-Chimica Sinica, ;2010, 26(07): 1811-1822. doi: 10.3866/PKU.WHXB20100722 shu

One-Pot Formation of Aromatic Oli amide Macrocycles and the Corresponding Mechanism

1.
Institute of Nuclear Science and Technology, Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
Department of Chemistry, University at Buffalo, The State University of New York at Buffalo, Buffalo, New York 14260, USA
College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China

Received Date: 26 January 2010
Available Online: 27 May 2010

In this review, we summarize a newly discovered one-pot process for the synthesis of aromatic oli amide and oli hydrazide macrocycles. A mechanism for these highly efficient one-pot macrocyclization reactions is presented and discussed. The unprecedented high efficiencies of these one-pot macrocyclization reactions are rationalized based on the folding of uncyclized oli meric precursors, which is enforced by intramolecular hydrogen bonds. These one-pot macrocyclization reactions, with their unusually high efficiencies and novel mechanism, afford several new classes of shape-persistent macrocycles that are otherwise difficult to obtain using traditional methods. It has been already demonstrated that these macrocycles possess unique properties in the specific recognition of guest species and the formation of highly conducting transmembrane pores.
- One-pot macrocyclization,
- Mechanism,
- Hydrogen bond,
- Shape-persistent macrocycle
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