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

ABSTRACT: 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 π-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 π-extended, highly fluorescent oligomers with a central deficient benzothiadiazole unit with up to nine aromatic rings through coupling reactions.

SUBMITTER: Nitti A

PROVIDER: S-EPMC7997634 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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

Nitti Andrea A Osw Peshawa P Calcagno Giuseppe G Botta Chiara C Etkind Samuel I SI Bianchi Gabriele G Po Riccardo R Swager Timothy M TM Pasini Dario D

Organic letters 20200407 8

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 π-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, ...[more]

PMID: 32255355

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