Electrochemical synthesis of α-enaminones from aryl ketones

2016 ◽  
Vol 52 (55) ◽  
pp. 8600-8603 ◽  
Author(s):  
Yanan Li ◽  
Huihui Gao ◽  
Zhenlei Zhang ◽  
Peng Qian ◽  
Meixiang Bi ◽  
...  

A novel approach to realize the synthesis of α-enaminones via electrochemical oxidation was developed under mild conditions.

1997 ◽  
Vol 75 (5) ◽  
pp. 499-506 ◽  
Author(s):  
E.H. De Oliveira ◽  
G.E.A. Medeiros ◽  
C. Peppe ◽  
Martyn A. Brown ◽  
Dennis G. Tuck

The electrochemical oxidation of a sacrificial metal anode (M = Zn, Cd, Cu) in an acetonitrile solution of 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone, lapachol, C15H14O3 (=HL) gives ML2. The results are in keeping with earlier work on direct electrochemical synthesis in related systems. Adducts with 2,2′-bipyridine (bpy) and N,N,N′,N′-tetramethylethanediamine (tmen) have also been prepared. The structure of the 2,2′-bipyridine adduct of Cu(lapacholate)2 has been established by X-ray crystallography. The parameters are triclinic, space group [Formula: see text], a = 12.748(59) Å, b = 13.859(49) Å, c = 11.770(59) Å, α = 108.30(4)°, β = 108.08(3)°, γ = 68.94(3)°, Z = 2, R = 0.059 for 2256 unique reflections. The copper atom is in a distorted CuN2O2O2′ environment. The mechanism of the formation of this Cu(lapacholate)2 is discussed. Keywords: electrochemical synthesis, lapachol, X-ray crystallography, copper(II) complex.


2018 ◽  
Vol 54 (80) ◽  
pp. 11340-11343 ◽  
Author(s):  
Yingying Tian ◽  
Eva Jürgens ◽  
Doris Kunz

The efficient and selective isomerisation of terminal epoxides into methyl ketones applying the nucleophilic Rh-catalyst 2LiX under mild conditions is reported.


2016 ◽  
Vol 40 (6) ◽  
pp. 5442-5447 ◽  
Author(s):  
Mahnaz Sharafi-Kolkeshvandi ◽  
Davood Nematollahi ◽  
Farzad Nikpour ◽  
Eslam Salahifar

Regioselective synthesis of 1-N-phenyl-4-(arylsulfonyl)benzene-1,2-diamine derivatives was carried out by the electrochemical oxidation of 2-aminodiphenylamine in aqueous solution in the presence of sulfinic acids as nucleophiles.


1980 ◽  
Vol 58 (16) ◽  
pp. 1673-1677 ◽  
Author(s):  
Farouq F. Said ◽  
Dennis G. Tuck

The electrochemical oxidation of titanium, zirconium, or hafnium (= M) in a cell containing an organic halicie RX results in the formation of an organometallic halide of the metal concerned. These compounds are conveniently isolated as adducts of acetonitrile or 2,2′-bipyridine(bipy) also présent in the electrolyte phase. The products most commonly isolated are the [Formula: see text], but other species were obtained in certain cases. Possible reasons for these findings are discussed.


Tetrahedron ◽  
1998 ◽  
Vol 54 (20) ◽  
pp. 5315-5324 ◽  
Author(s):  
Nadia Caposcialli ◽  
Carlo Dell'Erba ◽  
Marino Novi ◽  
Giovanni Petrillo ◽  
Cinzia Tavani

Synlett ◽  
2019 ◽  
Vol 30 (18) ◽  
pp. 2077-2080
Author(s):  
Wenxia Xie ◽  
Bowen Gong ◽  
Shulin Ning ◽  
Nian Liu ◽  
Zhuoqi Zhang ◽  
...  

A diethyl phosphite mediated electrochemical oxidation strategy for the synthesis of 3,4-dihydroisoquinolin-1(2H)-ones from tetrahydroisoquinolines under mild conditions has been developed. This protocol provides an environmentally friendly and simple way for the construction of C=O bonds in an undivided cell unit.


2020 ◽  
Vol 2020 (22) ◽  
pp. 3257-3260 ◽  
Author(s):  
Fangling Lu ◽  
Fengping Gong ◽  
Liangsen Li ◽  
Kan Zhang ◽  
Zhen Li ◽  
...  

2002 ◽  
Vol 2 ◽  
pp. 48-52 ◽  
Author(s):  
Zhirong Sun ◽  
Xiang Hu ◽  
Ding Zhou

Wastewater minimization in phenylacetaldehyde production by using indirect electrochemical oxidation of phenylethane instead of the seriously polluting traditional chemical process is described in this paper. Results show that high current efficiency of Mn(III) and high yield of phenylacetaldehyde can be obtained at the same sulfuric acid concentration (60%). The electrolytic mediator can be recycled and there will be no waste discharged.


1982 ◽  
Vol 60 (20) ◽  
pp. 2579-2582 ◽  
Author(s):  
N. Kumar ◽  
Dennis G. Tuck

The electrochemical oxidation of thorium into solutions of halogen (X2; X = Cl, Br) in acetonitrile yields the adducts ThX4•4CH3CN in good yield. With solutions of X2 + R4NX, the products are (R4N)2ThX6. Neutral chelate complexes such as Th(acac)4 (acac = 2,4-pentanedionate) can also be prepared in a one-step synthesis from the metal, but cationic complexes could not be obtained by electrochemical methods.


1987 ◽  
Vol 65 (6) ◽  
pp. 1336-1342 ◽  
Author(s):  
Raj K. Chadha ◽  
Rajesh Kumar ◽  
Dennis G. Tuck

The electrochemical oxidation of anodic copper or silver (= M) into non-aqueous solutions of RSH (R = alkyl, axyl) gives MISR as insoluble materials in high yield. In the presence of 1,10-phenanthroline (= L), the products are MISR•phen for M = Cu, but not Ag. Gold resists oxidation under such conditions, and AuISR (R = n-C4H9, C6H5) was obtained in only poor yield. The crystal structure of the solvated dimeric adduct [Cu(SC6H4CH3-o)•phen]2•CH3CN is triclinic, with a = 10.682(3) Å, b = 11.729(4) Å, c = 15.608(5) Å, α = 76.87(2)°, β = 76.35(2)°, γ = 68.07(2)°, V = 1742(1) Å3, Z = 2 and space group [Formula: see text]. The structure is based on a folded Cu2S2 ring with an unusually short Cu—Cu distance of 2.613(3) Å Each copper atom has CuS2N2 pseudo-tetrahedral stereochemistry, with Cu—S = 2.337 Å(av) and Cu—N = 2.10 Å(av).


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