Metal-free mechanochemical oxidations in Ertalyte® jars

被引：20

作者：

Porcheddu, Andrea ^{[1
]}

Delogu, Francesco ^{[2
]}

De Luca, Lidia ^{[3
]}

Fattuoni, Claudia ^{[1
]}

Colacino, Evelina ^{[4
,5
]}

机构：

[1] Univ Cagliari, Dipartimento Sci Chim & Geol, SS 554 Bivio Sestu, I-09042 Monserrato, Ca, Italy

[2] Univ Cagliari, Dipartimento Ingn Meccan Chim & Mat, Via Marengo 2, I-09123 Cagliari, Italy

[3] Univ Sassari, Dipartimento Chim & Farm, Via Vienna 2, I-07100 Sassari, Italy

[4] Univ Montpellier, 8 Rue Ecole Normale, F-34296 Montpellier 5, France

[5] ICGM, UMR CNRS UM ENSCM 5253, 8 Rue Ecole Normale, F-34296 Montpellier 5, France

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 15卷

关键词：

AZADO; Ertalyte (R); green chemistry; mechanochemistry; NaOCl center dot 5H(2)O; selective oxidation; TEMPO; PENTAHYDRATE NAOCL-CENTER-DOT-5H(2)O CRYSTALS; ALCOHOL OXIDATION; SELECTIVE OXIDATION; AEROBIC OXIDATION; MEDICINAL MECHANOCHEMISTRY; OXOAMMONIUM SALTS; MODEL COMPOUNDS; ALDEHYDES; TEMPO; KETONES;

D O I：

10.3762/bjoc.15.172

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aimed at eliminating or at least significantly reducing the use of solvents, sodium hypochlorite pentahydrate crystals (NaOCl center dot 5H(2)O) in the presence of a catalytic amount of a nitrosyl radical (TEMPO or AZADO) have been successfully used to induce mechanochemical oxidative processes on several structurally different primary and secondary alcohols. The proposed redox process is safe, inexpensive and performing effectively, especially on the macroscale. Herein, an Ertalyte (R) jar has been successfully used, for the first time, in a mechanochemical process.

引用

页码：1786 / 1794

页数：9

共 62 条

[41] An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives
Mocci, Rita.
De Luca, Lidia
Delogu, Francesco
Porcheddu, Andrea
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (19) : 3135 - 3144
[42] Synthesis and applications of optically active nitroxides
Naik, N
Braslau, R
[J]. TETRAHEDRON, 1998, 54 (5-6) : 667 - 696
[43] Development of a Large-Scale Copper(I)/TEMPO-Catalyzed Aerobic Alcohol Oxidation for the Synthesis of LSD1 Inhibitor GSK2879552
Ochen, Augustine
Whitten, Robert
Aylott, Helen E.
Ruffell, Katie
Williams, Glynn D.
Slater, Fiona
Roberts, Andrew
Evans, Paul
Steves, Janelle E.
Sanganee, Mahesh J.
[J]. ORGANOMETALLICS, 2019, 38 (01) : 176 - 184
[44] Sodium hypochlorite pentahydrate (NaOCl•5H2O) crystals; An effective re-oxidant for TEMPO oxidation
Okada, Tomohide
Asawa, Tomotake
Sugiyama, Yukihiro
Iwai, Toshiaki
Kirihara, Masayuki
Kimura, Yoshikazu
[J]. TETRAHEDRON, 2016, 72 (22) : 2818 - 2827
[45] Sodium Hypochlorite Pentahydrate (NaOCl•5H2O) Crystals as an Extraordinary Oxidant for Primary and Secondary Alcohols
Okada, Tomohide
Asawa, Tomotake
Sugiyama, Yukihiro
Kirihara, Masayuki
Iwai, Toshiaki
Kimura, Yoshikazu
[J]. SYNLETT, 2014, 25 (04) : 596 - 598
[46] Transition metal based catalysts in the aerobic oxidation of alcohols
Parmeggiani, Camilla
Cardona, Francesca
[J]. GREEN CHEMISTRY, 2012, 14 (03) : 547 - 564
[47] Ball milling: a green technology for the preparation and functionalisation of nanocellulose derivatives
Piras, Carmen C.
Fernandez-Prieto, Susana
De Borggraeve, Wim M.
[J]. NANOSCALE ADVANCES, 2019, 1 (03): : 937 - 947
[48] From Lossen Transposition to Solventless "Medicinal Mechanochemistry"
Porcheddu, A.
Delogu, F.
De Luca, L.
Colacino, E.
[J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (14) : 12044 - 12051
[49] Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations
Porcheddu, Andrea
Colacino, Evelina
Cravotto, Giancarlo
Delogu, Francesco
De Luca, Lidia
[J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 2049 - 2055
[50] Advances in organometallic synthesis with mechanochemical methods
Rightmire, Nicholas R.
Hanusa, Timothy P.
[J]. DALTON TRANSACTIONS, 2016, 45 (06) : 2352 - 2362

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