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Synthesis of π-conjugated Molecules Based on 3,4-dioxypyrroles via Pd-mediated Decarboxylative Cross-Coupling

Synthesis of π-conjugated Molecules Based on 3,4-dioxypyrroles via Pd-mediated Decarboxylative Cross-Coupling

Frank A Arroyave, John R Reynolds

J Org Chem. 2011 Nov 4;76(21):8621-8.

PMID: 21995562

Abstract:

A general scheme for the synthesis of π-conjugated molecules based on 3,4-dioxypyrroles is presented. The π-conjugated molecules were synthesized via Pd-mediated decarboxylative cross-coupling using various 3,4-propylenedioxypyrrole carboxylic acids and aryl bromides, including the base-sensitive electron acceptor 4,7-dibromobenzo[c][1,2,5]thiadiazole (BTD). N-Methylpyrrolidone was used as solvent, Pd(acac)(2) was employed as the palladium source and P(o-tol)(3) as the ligand. The methodology was applied to 3,4-dioxypyrrole monoacids and 3,4-dioxypyrrole diacids to produce multi-ring π-conjugated systems containing phenyl, thiophenyl, BTD, and pyridinyl units. In general, the method has yielded a practical approach for the synthesis of 3,4-dioxypyrrole-based π-conjugated molecules in acceptable to high yields of 44-94%.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP15155416	4,7-Dibromobenzo[c]-1,2,5-thiadiazole		15155-41-6	Price

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