Microwave-promoted radical addition/cyclization of biaryl vinyl ketones with diacyl peroxides in water under metal-free conditions

Abstract

This communication reports an efficient microwave promoted radical addition/cyclization of biaryl vinyl ketones with diacyl peroxides on(in) water under metal-free conditions. A series of 10-methyl-10-benzyl(alkyl)phenanthren-9(10H)-ones were obtained in high yields...

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics

“…2 In most cases, the homolytic cleavage of O–O bond in diacyl peroxide relies on transition metal catalysis and elevated reaction temperature (up to 100 °C) to generate the corresponding acyloxyl radical, which undergoes a subsequent decarboxylation process to afford the aryl radical or alkyl radical (Scheme 1). 3 Therefore, exploring novel strategies for transforming diacyl peroxides under metal-free and room-temperature conditions is highly desirable.…”

Radical-mediated sulfonylative/thiolative cyclization of biaryl enones to phenanthrone derivatives

“…The starting materials 1a , 1c , 1d , 1g , 1j , 1u , and 1v were synthesized following the literature procedures, and the spectral data were compared. 8,17…”

“…In a similar manner, recently, Li's research group reported an approach for the preparation of fluoro-alkylated phenanthrene-9(10 H )-ones from biaryl vinyl ketones (Scheme 1d). 8 Herein, a new supplementary method producing the hitherto unknown thio-functionalized phenanthrones and related compounds from the reaction of biaryl(heteroaryl)enones with sulfonyl (SO 2 R), thiotrifluoromethyl (SCF 3 ), and thiocyanato (SCN) radicals is presented (Scheme 1e). The developed method does not require any metal additives or higher temperature.…”