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Transition-Metal-Free Synthesis of C3-Arylated Benzofurans from Benzothiophenes and Phenols

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journal contribution
posted on 2019-03-08, 13:10 authored by K Yang, A Pulis, GJP Perry, DJ Procter
We report a transition-metal-free synthesis of benzofurans from benzothiophenes and phenols that exploits the unique reactivity of sulfoxides. Through a sequence involving an interrupted Pummerer reaction and [3,3] sigmatropic rearrangement, phenols can be combined with readily accessible yet synthetically unexplored benzothiophene S-oxides to provide C3-arylated benzofuran products. The products from this approach can undergo subsequent functionalization to gain access to a range of important benzofuran derivatives.

Funding

EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1)

History

Citation

Organic Letters, 2019, 20 (23), pp. 7498-7503

Author affiliation

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

Version

  • AM (Accepted Manuscript)

Published in

Organic Letters

Publisher

American Chemical Society

eissn

1523-7052

Copyright date

2018

Publisher version

https://pubs.acs.org/doi/10.1021/acs.orglett.8b03267

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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