Electrochemically-mediated C–H functionalization of allenes and 1,3-dicarbonyl compounds to construct tetrasubstituted furans

Abstract

C-H functionalization of allenes is an available strategy to construct heterocyclic compounds. Herein we propose a sus-tainable electrocatalytic C-H activation for the synthesis of novel highly functionalized tetrasubstituted furans, which...

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

“…He and co-workers 102 reported an oxidant-free current-induced synthesis of tetrasubstituted furans ( 92 ) via intermolecular cyclization of allenes ( 91 ) and 1,3-dicarbonyl compounds ( 50 ). In order to discover the most efficient reaction conditions, the initial pre-screening of the reaction was performed using 4-methoxyphenyl allene and ethyl (4-methoxybenzoyl)acetate as model substrate.…”

Recent advances in the electrochemical generation of 1,3-dicarbonyl radicals from C–H bonds

“…The electrochemical C-H activation for the synthesis of tetrasubstituted furans via the intermolecular cyclization of allenes and 1,3-dicarbonyl derivatives was developed by Tang and co-workers (Scheme 17). 43 This approach employs cheap Cp 2 Fe as a redox catalyst and avoids the need for stoichiometric oxidants and noble metal catalysts. Many tetrasubstituted furans are obtained with satisfactory yields under simple electrochemical conditions, and one of these products exhibited good antitumor activity against the T-24 tumor cell line.…”

DFT computational insight into Pd(0)-catalyzed oxidative cross-coupling of 1,2-allenyl ketones and aryl boronic acids: Pd(ii)-carbenoid intermediate versus π-allyl-Pd(ii) intermediate

“…[1][2][3][4] Moreover, furan-based functional molecules have potential applications in materials science, especially in the field of furan-based semiconductors for energy conversion and storage. 5 The past decades have witnessed great advancements in furan syntheses using various methods, [6][7][8][9][10] in which the transition-metal-catalyzed cycloisomerization of 1,2-allenyl ketones has attracted remarkable attention [11][12][13][14][15] due to their availability 16,17 (Scheme 1a). The efficient syntheses of furan derivatives via the intramolecular nucleophilic cyclization of 1,2-allenyl ketones were initially reported by Marshall 13 and Hashmi et al 14 (Scheme 1a with G = H, M = Rh I , Ag I , or Pd II ) and subsequently developed by Gevorgyan et al 15 (Scheme 1a with G = alkyl, aryl, halide, silyl, etc., M = Au I , Ag I , Cu I , etc.)…”