Free‐radical Initialized Cyclization of 2‐(3‐Arylpropioloyl)benzaldehydes with Toluene Derivatives: Access to Benzylated 1,4‐Naphthoquinones via Copper‐Catalyzed Cascade Reaction

Abstract

A copper‐catalyzed cyclization reaction of 2‐(3‐arylpropioloyl)benzaldehydes was developed, leading to benzylated 1,4‐naphthoquinones via radical‐triggered cascade cyclization. This example of an acylbenzylation involving internal alkynes could be carried out with a broad substrate scope and wide functional group tolerance.

Highly Stereoselective Intramolecular Carbofluorination of Internal α,β-Ynones Promoted by Selectfluor

“…However, the use of Selectfluor as a tetrafluoroborate anion (BF 4 – ) donor species has been poorly explored in nucleophilic fluorinated reactions. Based on previous work carried out in our laboratory, herein we report an intramolecular carbofluorination of internal alkynes (Scheme c). This method provided high regioselectivity and a broad substrate scope, thus offering a novel pathway to prepare diverse 3-hydroxy-1-indanones with a monofluoroalkene motif under simple reaction conditions.…”

Photoinduced Three-Component Difluoroamidosulfonylation/Bicyclization: A Route to Dihydrobenzofuran Derivatives

“…17 Over the past few decades, a threecomponent methodology that uses easily handled DABCO• (SO 2 ) 2 as a convenient sulfur dioxide surrogate for the installation of a sulfonyl group has received increased attention. 18 Therefore, with our ongoing studies on radical cyclization, 19 we disclose the visible-light-induced threecomponent radical tandem bicyclization of N-allylbromodifluoroacetamides and terminal alkynes with the insertion of sulfur dioxide under external-oxidant-free and photocatalystfree conditions. We initiated our studies by employing 1-ethynyl-2isopropoxybenzene (1a) and N-allylbromodifluoroacetamides (2a) as the model substrates, DABCO•(SO 2 ) 2 as the sulfur dioxide surrogate, and NaHCO 3 as the base; the reaction was performed under the irradiation of a 40 W blue-light LED lamp for 12 h at room temperature, and 3aa was obtained in a 37% yield (Table 1, entry 1).…”

A Forward Vision for Chemodynamic Therapy: Issues and Opportunities

“…[22] Notably, the core mechanism for Fenton reactions is the interactions of the electrons between the d-orbital of Fe and the OÀ O bond of H 2 O 2 . Thus, Fe-mediated OÀ O bond cleavage may be generalized to other peroxide-containing species, such as lauroyl peroxide, butyl peroxide, and cumene hydroperoxide, [23] thereby generating abundant radical species to induce distinct biological effects.…”