2020
DOI: 10.1021/acs.orglett.0c01043
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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, benzo… Show more

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Cited by 32 publications
(24 citation statements)
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“…Moreover, synthetic access to this scaffold remains relevant as can be seen from recent works in carbonylation, 26 in carbocyclization, [27][28][29] direct functionalization 30,31 or in annulation of thiophene heterocycles. [32][33][34][35] Therefore, the present study has been done to explore the possible functionalization of aminothiaindanone scaffold with three diversity points: first on the thiophene ring, second on the amine group, and finally third on the ketone part of the scaffold.…”
Section: Aminothiaindanone As An Accessible Scaffold For a Three-point Chemical Diversitymentioning
confidence: 99%
“…Moreover, synthetic access to this scaffold remains relevant as can be seen from recent works in carbonylation, 26 in carbocyclization, [27][28][29] direct functionalization 30,31 or in annulation of thiophene heterocycles. [32][33][34][35] Therefore, the present study has been done to explore the possible functionalization of aminothiaindanone scaffold with three diversity points: first on the thiophene ring, second on the amine group, and finally third on the ketone part of the scaffold.…”
Section: Aminothiaindanone As An Accessible Scaffold For a Three-point Chemical Diversitymentioning
confidence: 99%
“…Several researchers focused on progresses in catalysis and reaction engineering that conducted to waste and energy reduction for techniques that remain constitute important dares [2]. Some scientists concentrated on usage of less toxic reagents, catalysts, or routes [60][61][62]. In terms of catalysis front, there is an augmentation in the field of synthetic transformations assisted by supported catalysts [63,64].…”
Section: Reducing the Effect Of Chemical Synthesis And Manufacturingmentioning
confidence: 99%
“…Monomers with a fused aromatic structure can be synthesized via direct arylation and subsequent cyclization reactions. [ 42–45 ] Indacenodithiophene (IDT) is a promising building block for conjugate polymers; [ 46 ] however, its tedious synthetic pathway is a drawback. Introduction of thiophene units by direct arylation and double cyclization offers a straightforward route for the preparation of IDT derivatives ( Scheme ).…”
Section: Monomer Synthesis Via Direct Ch Arylation and Subsequent Direct Arylation Polycondensationmentioning
confidence: 99%