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1. Photochemical oxidation of benzylic primary and secondary alcohols utilizing air as the oxidant

Author:
Triandafillidi, Ierasia,   et al.   ; Nikitas, Nikolaos F.; Tzaras, Dimitrios Ioannis; Kokotos, Christoforos G.;     Show all 4 Authors
Source:
Green chemistry 2020 v.22 no.2 pp. 471-477
ISSN:
1463-9270
Subject:
air; alcohols; aldehydes; green chemistry; ketones; lamps; oxidants; oxidation; oxygen; photocatalysts; photochemistry; reaction mechanisms; solar radiation
Abstract:
... A mild and green photochemical protocol for the oxidation of alcohols to aldehydes and ketones was developed. Utilizing thioxanthenone as the photocatalyst, molecular oxygen from air as the oxidant and cheap household lamps or sunlight as the light source, a variety of primary and secondary alcohols were converted into the corresponding aldehydes or ketones in low to excellent yields. The reaction ...
DOI:
10.1039/c9gc03000j

2. Synthesis of γ-Lactones Utilizing Ketoacids and Trimethylsulfoxonium Iodide

Author:
Triandafillidi, Ierasia,   et al.   ; Savvidou, Anatoli; Kokotos, Christoforos G.;     Show all 3 Authors
Source:
Organic letters 2019 v.21 no.14 pp. 5533-5537
ISSN:
1523-7052
Subject:
carbonyl compounds; chemical structure; epoxidation reactions; epoxides; lactones
Abstract:
... The Johnson–Corey–Chaykovsky epoxidation is one of the oldest methods for the synthesis of terminal epoxides from carbonyl compounds. Herein we present a simplified extension of the Johnson–Corey–Chaykovsky epoxidation, where ketoacids are employed as the substrates and commercially available trimethylsulfoxonium iodide is employed as the carbon-atom homologating reagent. A variety of lactones are ...
DOI:
10.1021/acs.orglett.9b01852

3. Photo-organocatalytic synthesis of acetals from aldehydes

Author:
Triandafillidi, Ierasia,   et al.   ; Nikitas, Nikolaos F.; Kokotos, Christoforos G.;     Show all 3 Authors
Source:
Green chemistry 2019 v.21 no.3 pp. 669-674
ISSN:
1463-9270
Subject:
aldehydes; green chemistry; lamps; photocatalysts; reaction mechanisms
Abstract:
... A mild and green photo-organocatalytic protocol for the highly efficient acetalization of aldehydes has been developed. Utilizing thioxanthenone as the photocatalyst and inexpensive household lamps as the light source, a variety of aromatic and aliphatic aldehydes have been converted into acyclic and cyclic acetals in high yields. The reaction mechanism was extensively studied. ...
DOI:
10.1039/c8gc03605e

4. Green Organocatalytic Synthesis of Isoxazolines via a One-Pot Oxidation of Allyloximes

Author:
Triandafillidi, Ierasia,   et al.   ; Kokotos, Christoforos G.;     Show all 2 Author
Source:
Organic letters 2017 v.19 no.1 pp. 106-109
ISSN:
1523-7052
Subject:
catalytic activity; hydrogen peroxide; moieties; organic compounds; oxidants; oxidation
Abstract:
... A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H₂O₂ as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromati ...
DOI:
10.1021/acs.orglett.6b03380

5. Photocatalytic Synthesis of γ-Lactones from Alkenes: High-Resolution Mass Spectrometry as a Tool To Study Photoredox Reactions

Author:
Triandafillidi, Ierasia,   et al.   ; Kokotou, Maroula G.; Kokotos, Christoforos G.;     Show all 3 Authors
Source:
Organic letters 2018 v.20 no.1 pp. 36-39
ISSN:
1523-7052
Subject:
alkenes; chemical structure; mass spectrometry; monitoring; photocatalysis; photocatalysts; protocols; redox reactions
Abstract:
... A mild photocatalytic manifold for the synthesis of γ-lactones has been developed. Utilizing Ru(bpy)₃Cl₂ as the photocatalyst, a cheap and reproducible synthetic protocol for γ-lactones has been introduced. Mechanistic studies revealed the successful monitoring of photocatalytic reactions and radical intermediates via high-resolution mass spectrometry. ...
DOI:
10.1021/acs.orglett.7b03256

6. tert-Butyl ester or benzylamide of the dipeptide Pro-Gly as organocatalysts for the asymmetric aldol reaction

Author:
Triandafillidi, Ierasia,   et al.   ; Bisticha, Aikaterini; Voutyritsa, Errika; Galiatsatou, Gerasimia; Kokotos, Christoforos G.;     Show all 5 Authors
Source:
Tetrahedron 2015 v.71 pp. 932-940
ISSN:
0040-4020
Subject:
acetonitrile; aldehydes; amides; chemical reactions; dipeptides; enantiomers; esters; glycine (amino acid); ketones; proline; solubility
Abstract:
... A family of dipeptides consisting of proline and tert-butyl esters of amino acids, as well as simple amides of prolyl-glycine dipeptide were synthesized and tested for their organocatalytic properties on the intermolecular asymmetric aldol reaction. The peptides were tested both in organic and aqueous media. Among the peptides tested, Pro-Gly-OtBu afforded the best results in acetonitrile, while P ...
DOI:
10.1016/j.tet.2014.12.078