Abstract: The [1,2]-aryl shift reaction was used to synthesize naphtho[2,1-b]furans as promising fluorescent scaffolds for organic electronics. The target compounds are furan analogues of phenanthrene formally accessed by isosteric replacement of the CH[double bond, length as m-dash]CH moiety with an oxygen atom. The straightforward and robust approach involving a [1,2]-aryl shift as a key step provides easy access to a wide range of naphtho[2,1-b]furans with the possibility of late-stage functionalization. Efficient switching of the regioselectivity of acid-catalyzed reactions of arylnaphtho[2,1-b]furans via a [1,2]-aryl shift has been demonstrated. A one-pot protocol involving sequential intramolecular condensation/[1,2]-aryl shift/intermolecular oxidative aromatic coupling to provide access to binaphtho[2,1-b]furan analogues of BINOL was developed. The advantage of these compounds lies in the strong variation in chemical properties and spectral performance depending on the nature and position of the aryl substituent, which facilitates the synthesis of compounds with desired spectral characteristics and opens up prospects for their further use in electronics, biotechnologies and organic synthesis.

Cite: Mekeda I.S. , Balakhonov R.Y. , Shirinian V.Z.
Switching the regioselectivity of acid-catalytic reactions of arylnaphtho[2,1-b]furans via [1,2]-aryl shift
Organic & Biomolecular Chemistry. 2024. V.22. N37. P.7715-7724. DOI: 10.1039/d4ob01223b WOS Scopus OpenAlex

Identifiers:

Web of science:	WOS:001304228900001
Scopus:	2-s2.0-85202919399
OpenAlex:	W4401942388

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