ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
0/0

Short Syntheses of 1-Substituted Dibenzothiophenes and 3-Substituted Naphthothiophenes

preprint
submitted on 29.09.2019 and posted on 01.10.2019 by Erin N. Welsh, Emily K. Burke, Katherine Roberston, Alex Speed

The 1-substituted dibenzothiophene motif is an unusual substitution pattern. We demonstrate a simple one-pot preparation of 1-lithiodibenzothiophene via a cascade of two benzyne additions and conversion to the aldehyde, boronic ester, and iodide. This work avoids the use of precious metals or tert-butyllithium and is shorter than existing routes to these compounds. We also report an improved route to the isomeric 3-substituted naphthothiophene scaffold. These protocols will allow rapid access to families of these two related heteroacenes.

Funding

NSERC Discovery

NSERC I2I

Nova Scotia Graduate Scholarship

Labrador Student Support

History

Email Address of Submitting Author

aspeed@dal.ca

Institution

Dalhousie University

Country

Canada

ORCID For Submitting Author

0000-0002-8997-3807

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version one

Exports

Logo branding

Exports