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Metal-Free Synthesis of Benzothiophenes by Twofold C–H Functionalization: Direct Access to Materials-Oriented Heteroaromatics

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journal contribution
posted on 2019-09-17, 14:49 authored by Jiajie Yan, Alexander P. Pulis, Gregory J. P. Perry, David John Procter
Due to their ubiquity in nature and frequent use in organic electronic materials, benzothiophenes are highly sought after. Here we set out an unprecedented procedure for the formation of benzothiophenes via the dual vicinal C–H functionalization of arenes that does not require metal catalysis. This one‐pot annulation proceeds through an interrupted Pummerer reaction/[3,3]‐sigmatropic rearrangement/cyclization sequence to deliver various benzothiophene products. The procedure is particularly effective for the rapid synthesis of benzothiophenes from non‐prefunctionalized polyaromatic hydrocarbons (PAHs).

Funding

We thank the EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1), the University of Manchester (Lectureships to A.P.P. and G.J.P.P) and the Swedish Chemical Society (Stiftelsen Bengt Lundqvists Minne Postdoc Fellowship to J.Y.). We thank the Manchester X-ray Crystallography Service. Finally, we thank Prof. Kenichiro Itami, Assoc. Prof. Kei Murakami, Assoc. Prof. Hideto Ito, Mr Wataru Matsuoka, Ms Shu Jan Yip, Mr Kou Kawahara and all the Itami group for discussions and for the gift of corannulene.

History

Citation

Angewandte Chemie - International Edition, 2019

Author affiliation

/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of Chemistry

Version

  • AM (Accepted Manuscript)

Published in

Angewandte Chemie - International Edition

Publisher

Wiley for Gesellschaft Deutscher Chemiker (GDCh)

issn

0570-0833

Acceptance date

2019-09-03

Copyright date

2019

Publisher version

https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201908319

Notes

The file associated with this record is under embargo until 12 months after publication, in accordance with the publisher's self-archiving policy. The full text may be available through the publisher links provided above.

Language

en

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