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Title: Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings
Authors: G.-F. Huo
T. M. Fukunaga
X. Hou 
Y. Han 
W. Fan 
S. Wu 
H. Isobe
J. Wu 
Issue Date: 23-Feb-2023
Publisher: Wiley
Citation: G.-F. Huo, T. M. Fukunaga, X. Hou, Y. Han, W. Fan, S. Wu, H. Isobe, J. Wu (2023-02-23). Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings. Angew. Chem. Int. Ed. 62 (18) : e202218090. ScholarBank@NUS Repository.
Rights: Attribution 4.0 International
Abstract: Expanded helicenes are expected to show enhanced chiroptical properties as compared to the classical helicenes but the synthesis is very challenging. Herein, we report the facile synthesis of a series of expanded helicenes Hn (n=1–4) containing 11, 19, 27 and 35 cata-fused benzene rings through Suzuki coupling-based oligomerization followed by Bi(OTf)3-mediated regioselective cyclization of vinyl ethers. Their structures were determined by X-ray crystallographic analysis. Enantiopure H2, H3, and H4 can be isolated by chiral HPLC and they all exhibit strong chiroptical responses with high absorption dissymmetry factor (|gabs|) values (0.020 for H2, 0.021 for H3, and 0.021–0.024 for H4).
Source Title: Angew. Chem. Int. Ed.
ISSN: 1433-7851
DOI: 10.1002/anie.202218090
Rights: Attribution 4.0 International
Appears in Collections:Staff Publications

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