Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings**

Gui Fei Huo; Toshiya M. Fukunaga; Xudong Hou; Yi Han; Wei Fan; Shaofei Wu; Hiroyuki Isobe; Jishan Wu

doi:10.1002/anie.202218090

Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings**

Gui Fei Huo, Toshiya M. Fukunaga, Xudong Hou, Yi Han, Wei Fan, Shaofei Wu^*, Hiroyuki Isobe^*, Jishan Wu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

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 (|g_abs|) values (0.020 for H2, 0.021 for H3, and 0.021–0.024 for H4).

Original language	English
Article number	e202218090
Journal	Angewandte Chemie - International Edition
Volume	62
Issue number	18
DOIs	https://doi.org/10.1002/anie.202218090
Publication status	Published - 24 Apr 2023
Externally published	Yes

Keywords

Benzannulation
Chiral Molecules
Circular Dichroism
Expanded Helicenes
Polyarenes

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10.1002/anie.202218090

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title = "Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings**",

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).",

keywords = "Benzannulation, Chiral Molecules, Circular Dichroism, Expanded Helicenes, Polyarenes",

author = "Huo, \{Gui Fei\} and Fukunaga, \{Toshiya M.\} and Xudong Hou and Yi Han and Wei Fan and Shaofei Wu and Hiroyuki Isobe and Jishan Wu",

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year = "2023",

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doi = "10.1002/anie.202218090",

language = "English",

volume = "62",

journal = "Angewandte Chemie - International Edition",

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T1 - Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings**

AU - Huo, Gui Fei

AU - Fukunaga, Toshiya M.

AU - Hou, Xudong

AU - Han, Yi

AU - Fan, Wei

AU - Wu, Shaofei

AU - Isobe, Hiroyuki

AU - Wu, Jishan

PY - 2023/4/24

Y1 - 2023/4/24

N2 - 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).

AB - 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).

KW - Benzannulation

KW - Chiral Molecules

KW - Circular Dichroism

KW - Expanded Helicenes

KW - Polyarenes

UR - https://www.scopus.com/pages/publications/85150655838

U2 - 10.1002/anie.202218090

DO - 10.1002/anie.202218090

M3 - Article

C2 - 36826385

AN - SCOPUS:85150655838

SN - 1433-7851

VL - 62

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 18

M1 - e202218090

ER -

Facile Synthesis and Chiral Resolution of Expanded Helicenes with up to 35 cata-Fused Benzene Rings**

Abstract

Keywords

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