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An unexpected rearrangement aromatization of benzo[c]oxepine has been revealed to synthesize substituted naphthalenes. This observation was further exploited to develop an efficient approach for the construction of naphthalenes from simple and commercially available 1,3-dicarbonyl compounds and 1,2-bis(halomethyl)benzene compounds via a new domino reaction sequence.
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http://dx.doi.org/10.1021/ol302950w | DOI Listing |
Tetrahedron
August 2024
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, IL, 61801, USA.
A dearomative 1,4-hydroamination of nonactivated arenes has been developed, using a key arene-arenophile photocycloaddition strategy to disrupt aromaticity. Palladium catalysis with K-Selectride as a hydride source uniquely enables selective reactivity and provides access to a range of substituted 1,4-cyclohexadienes from aromatic starting materials. We demonstrate a few synthetic applications of this scalable procedure by preparing highly-functionalized small molecules in three to four steps from naphthalene.
View Article and Find Full Text PDFFront Plant Sci
August 2025
Department of Biotechnology, Central University of South Bihar, Gaya, Bihar, India.
The plant (Asteraceae) is gaining popularity as a zero-calorie natural sugar substitute. This paper investigates the regeneration of from callus, emphasizing steviol glycoside (SGs) production and the evaluation of genetic similarity. The highest rate of callus induction (89.
View Article and Find Full Text PDFOrg Lett
September 2025
Department of Chemistry, Indian Institute of Technology Delhi, Hauz Khas, New Delhi, 110016, India.
Herein, we report a regioselective [4 + 2] benzannulation strategy for the efficient synthesis of -terphenyls and naphthalenes from vinyl sulfoxonium ylides, thiophenols, and electron-deficient alkynes. The selectivity of the benzannulation is governed by the nature of the ylide's stabilizing group. This modular approach features a broad substrate scope and enables streamlined access to highly substituted arenes with significant synthetic versatility.
View Article and Find Full Text PDFChemistry
September 2025
Institute of Chemistry, Carl von Ossietzky Universität Oldenburg, Carl von Ossietzky-Str. 9-11, Oldenburg, D-26129, Federal Republic of Germany, European Union.
The synthesis of a series of selanyl-stabilized cationic silyl Lewis acids with naphthalene or acenaphthalene scaffolds is described. The influence of scaffold modifications, substitution variations at the selanyl donor and at the silicon atom on the strengths of the silyl Lewis acid is evaluated using the p-fluorobenzonitrile (FBN) method. These simple variations of the principal structure allow to adjust the Lewis acidity of the cationic silyl Lewis acids from weak ones to examples that are significantly stronger than tris(pentafluorophenyl)borane (BCF).
View Article and Find Full Text PDFRSC Med Chem
August 2025
Chinese Medicine Research and Development Center, China Medical University Hospital Taichung 404332 Taiwan
Natural products are an important source for developing anti-cancer agents. Previously, we identified the anti-cancer flavonoid protoapigenone from (Gaud.) and synthesized its derivative, WYC-0209, with improved anti-cancer properties.
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