Silver-catalysed three-component reactions of alkynyl aryl ketones, element selenium, and boronic acids leading to 3-organoselenylchromones

Abstract

An Ag-catalysed three-component reaction of alkynyl aryl ketones bearing an ortho-methoxy group, element selenium, and aryl boronic acid, providing a facile route to selenofunctionalized chromone product has been developed. This...

Ag(i)-catalyzed three-component radical cascade synthesis of 3-organoselenyl chromones from 2-methoxyaryl alkynones, Se powder and organic boronic acids

“…This competitive diaryl diselenide formation from arylboronic acids and Se powder under similar reaction conditions has already been documented in previous research. 9,25 To our delight, this side reaction can be dramatically restrained by the addition of a catalytic amount of either cationic surfactant (CTAC, CTAB and DTAB) or anionic surfactant SDS (entries 2-5, Table 1). In these cases, the by-product 4a was reduced to less than 7%, and the targeted product 3aa was significantly increased to excellent yields (83-89%).…”

Electrochemical Selenylation of Alkynyl Aryl Ketones: Efficient Synthesis of 3‐Selenylated Chromones under Catalyst‐ and Chemical‐Oxidant‐Free Conditions

“…Reactions were monitored by thin-layer chromatography (TLC). 1 H NMR, 13 C NMR, and 19 F NMR spectra were recorded at room temperature on a Bruker ADVANCE III spectrometer ( 1 H 500 MHz, 13 C 125 MHz, and 19 F 471 MHz, respectively) and were reported relative to residual CDCl 3 (δ 7.26 ppm and 77.16 ppm, respectively). Data for 1 H NMR were reported as chemical shift (δ ppm) (multiplicity, coupling constant (Hz), integration) using standard abbreviations for multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet.…”

“…Additional references were cited within the Supporting Information. [9][10][11][12][13][14][15][16][17][18]…”

“…To date, the research on developing the synthetic methodology for such moieties is well-established (Scheme 1). [9][10][11][12][13] However, most of them run in harsh conditions and suffer from some shortcomings, for instance, the requirement of high loading amount of transition-metal salt, excess strong oxidant, high temperature, and low efficiency. These drawbacks are usually unavoidable and decrease the practicability of these kinds of methods.…”

Silver-catalyzed synthesis of nitrogen heterocycles: recent advancements

“…38 This is literally proved by a comprehensive book on silver catalysis 39 split into two volumes and comprising more than 2000 schemes. Silver-catalyzed cyclizations, 40 alkynylations, 41 Diels-Alder reactions, 42 reductions, 43 oxidations, 44 cross-coupling reactions, 45 Michael additions, 46 Friedel-Crafts reactions, 47 A3-coupling reactions 48 and total synthesis 49 are extensively explored. Silver catalysis shows unique properties such as efficiency, stability and excellent selectivity.…”