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

01 October 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

dibenzothiophene
naphthothiophene
boronic ester
benzyne

Supplementary materials

Title
Description
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Title
SI dibenzothiophene
Description
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