3226-15-1Relevant articles and documents
Aroyl Fluorides as Bifunctional Reagents for Dearomatizing Fluoroaroylation of Benzofurans
Yu, Xiaoye,Meng, Qing-Yuan,Daniliuc, Constantin G.,Studer, Armido
, p. 7072 - 7079 (2022/04/12)
The 2,3-dihydrobenzofuran scaffold is widely found in natural products and biologically active compounds. Herein, dearomatizing 2,3-fluoroaroylation of benzofurans with aroyl fluorides as bifunctional reagents to access 2,3-difunctionalized dihydrobenzofurans is reported. The reaction that occurs by cooperative NHC/photoredox catalysis provides 3-aroyl-2-fluoro-2,3-dihydrobenzofurans with moderate to good yield and high diastereoselectivity. Cascades proceed via radical/radical cross-coupling of a benzofuran radical cation generated in the photoredox catalysis cycle with a neutral ketyl radical formed through the NHC catalysis cycle. The redox-neutral transformation exhibits broad substrate scope and high functional group compatibility. With anhydrides as bifunctional reagents, dearomatizing aroyloxyacylation of benzofurans is achieved and the strategy can also be applied to N-acylated indoles to afford 3-aroyl-2-fluoro-dihydroindoles.
Piperidine-mediated annulation of 2-acylphenols with 4-nitrobenzaldehyde to 3-benzofuranones
Verma, Nishant,Kundi, Varun,Ahmed, Naseem
supporting information, p. 4175 - 4179 (2015/06/22)
Piperidine - mediated reactions of 2-acylphenols and 4-nitrobenzaldehydes afforded 3-benzofuranones in high yield (82-95%) at reflux temperature in ethanol. The electron density calculation of HOMO-LUMO energy in the chalcone intermediates by DFT showed t
TMSOTf-promoted addition of alkynes to aldehydes: A novel synthesis of chroman-4-ones
Ji, Yeon Park,Ullapu, Punna Reddy,Choo, Hyunah,Jae, Kyun Lee,Min, Sun-Joon,Ae, Nim Pae,Kim, Youseung,Baek, Du-Jong,Yong, Seo Cho
experimental part, p. 5461 - 5469 (2009/05/07)
A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.