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Functionalization of the "Bay Region" of Perylene in Reaction With 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ Ghi]perylenes

Functionalization of the "Bay Region" of Perylene in Reaction With 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ Ghi]perylenes

Marta Głodek, Anna Makal, Damian Plażuk

J Org Chem. 2018 Nov 16;83(22):14165-14174.

PMID: 30354122

Abstract:

We describe a convenient method of the synthesis of 1-acyl-2-alkylbenzo[ ghi]perylenes via functionalization of the "bay region" of perylene in the reaction with 1-arylalk-2-yn-1-ones catalyzed by trifluoromethanesulfonic acid. We showed that the formation of 1-acyl-2-alkylbenzo[ ghi]perylenes from perylene and 1-arylalk-2-yn-1-ones might occur via spontaneous aromatization of 1-acyl-2-alkyl-2a,12a-dihydrogenbenzo[ ghi]perylenes by oxidation with dioxygen or by the hydrogen transfer to 1-arylalk-2-yn-1-ones. These compounds are fluorescent in solution with a high Stokes shift and with a ΦF value of up to 0.17 (and 0.36 in solid).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP60669694	Dibutylboryl trifluoromethanesulfonate solution		60669-69-4	Price

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