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Metal-Free Synthesis of Benzothiophenes by Twofold C–H Functionalization: Direct Access to Materials-Oriented Heteroaromatics
journal contribution
posted on 2019-09-17, 14:49 authored by Jiajie Yan, Alexander P. Pulis, Gregory J. P. Perry, David John ProcterDue 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, 2019Author affiliation
/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of ChemistryVersion
- AM (Accepted Manuscript)
Published in
Angewandte Chemie - International EditionPublisher
Wiley for Gesellschaft Deutscher Chemiker (GDCh)issn
0570-0833Acceptance date
2019-09-03Copyright date
2019Publisher DOI
Publisher version
https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201908319Notes
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
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