One-Pot Regiodirected Annulations for the Rapid Synthesis of pi-Extended Oligomers.

2020 
We demonstrate the broad applicability of the annulation protocol combining, in one pot, a direct arylation and cross aldol condensation for the straightforward synthesis at gram-scale of pi-extended thiophene-based scaffolds. The regiospecific direct arylation drives the subsequent cross-aldol condensation proceed under the same basic conditions, and the overall protocol has broad applicability in the synthesis of extended aromatics wherein the thiophene ring is annulated with furans, pyridines, indoles, benzothiophenes, and benzofurans. These scaffolds can be further elaborated into pi-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.
    • Correction
    • Source
    • Cite
    • Save
    • Machine Reading By IdeaReader
    42
    References
    9
    Citations
    NaN
    KQI
    []