Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
5 years ago

Corona[5]arenes Accessed by a Macrocycle-to-Macrocycle Transformation Route and a One-Pot Three-Component Reaction

Corona[5]arenes Accessed by a Macrocycle-to-Macrocycle Transformation Route and a One-Pot Three-Component Reaction
Zhi-Chen Wu, Qing-Hui Guo, Mei-Xiang Wang
Corona[5]arenes, a novel type of macrocyclic compound that is composed of alternating heteroatoms and para-arylenes, were synthesized efficiently by two distinct methods. In a macrocycle-to-macrocycle transformation approach, S6-corona[3]arene[3]tetrazine underwent sequential SNAr reactions with HS-C6H4-X-C6H4-SH (X=S, CH2, CMe2, SO2, and O) to produce the corresponding corona[3]arene[2]tetrazines. Different corona[3]arene[2]tetrazine compounds were also constructed in a straightforward manner by a one-pot three-component reaction of HS-C6H4-X-C6H4-SH (X=S, CH2, CMe2, SO2, and O) with diethyl 2,5-dimercaptoterephthalate and 2 equiv of 3,6-dichlorotetrazine under very mild conditions. All corona[5]arenes adopted 1,2,4-alternate conformational structures in the crystalline state yielding similar nearly regular pentagonal cavities. Both the cavity size and the electronic property of the acquired macrocycles were fine-tuned by the nature of the bridging element X. Corona[3]arene[2]tetrazines with a coronary conformational structure and finely tunable cavity and electronic properties were synthesized by a macrocycle-to-macrocycle transformation route and a one-pot three-component reaction.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703008

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