2006
DOI: 10.1016/j.tet.2006.03.062
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Generation of ketyl radical anions by photoinduced electron transfer (PET) between ketones and amines. Synthetic applications

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Cited by 76 publications
(37 citation statements)
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“…Photoinduced electron transfer (PET) is a feasible reaction between ketone or aromatic hydrocarbon photosensitizers and amines [26][27][28][29]. Being a secondary amine, TEMP (E ox = 1.0 V vs SCE) [45] could be oxidized by PET if the process is thermodynamically allowed.…”
Section: Electron Transfer Oxidation Of Temp To Tempomentioning
confidence: 99%
See 1 more Smart Citation
“…Photoinduced electron transfer (PET) is a feasible reaction between ketone or aromatic hydrocarbon photosensitizers and amines [26][27][28][29]. Being a secondary amine, TEMP (E ox = 1.0 V vs SCE) [45] could be oxidized by PET if the process is thermodynamically allowed.…”
Section: Electron Transfer Oxidation Of Temp To Tempomentioning
confidence: 99%
“…Although the TEMPO/EPR method has been largely employed [17][18][19][20][21][22][23][24][25], a systematic investigation of the scope and limitations of this technique has never been performed. For instance, amines are widely known for their quenching ability of excited states, so a probable source of artefacts may be the interaction between the excited photosensitizer and TEMP [26][27][28][29]. The aim of the present study is to compare the results obtained for the detection and quantification of singlet oxygen by means of the direct method (TRNIR emission) and the indirect 1 O 2 trapping mode (TEMPO/EPR method), using a set of well known photosensitizers.…”
Section: Introductionmentioning
confidence: 99%
“…There have been a number of specialist reviews providing comprehensive coverage of various aspects of radical chemistry published over the last five years; topics covered include free-radical cascade processes, 3 the synthesis of heterocycles by radical cyclisations, 4 the synthesis of five-and six-membered heterocycles, 5a,b 5-endo-trig cyclisations, 6 the formation of five-membered rings by translocation-cyclisation, 7 unusual radical cyclisations, 8 radical reactions in aqueous media, 9 the chemistry of ketyl radical anions formed by photoinduced electron transfer, 10 the addition of radicals to C]N bonds, 11,12 'clean' radical reagents, 13 phosphorus-based radical methodology, 14 indium and indium reagents in organic synthesis, 15a,b dichloroindane as a versatile reducing agent, 16 titanocene-mediated radical reactions, 17a,b copper(I)-catalysed atom transfer radical cyclisations, 18 atom transfer radical polymerisations (ATRP), 19a,b samarium(II) iodide in organic synthesis, [20][21][22] samarium(II) iodide in asymmetric synthesis, 23 transition metal generated radicals, 24 cerium regents in synthesis, 25 the persistent radical effect, 26a,b cyclohexa-1,4-diene-based radical reagents, 27 radical additions to aromatic systems, 28 diastereoselective radical reactions, 29a,b enantioselective radical reactions, 30-32 stereoselective conjugate additions. 33,34 radical carbonylations, 35 O-centred radicals in C-O bond formation, 36 inorganic radical reagents, 37 radical chemistry of organoboranes, 38a,b the addition of phosphorus compounds to unactivated hydrocarbons, 39 nitrogen-directed radical rearrangements, 40 thiol-mediated radical cyclisations, 41 the chemistry of N-centred radicals, 42 chirality control in photochemical reactions 43 and the carbometallation of unactivated alkenes by zinc enolate derivatives.…”
Section: Introductionmentioning
confidence: 99%
“…Although the TEMPO/EPR method has been largely employed [22,[99][100][101][102][103][104][105][106], a systematic investigation of the scope and limitations of this technique has never been performed, so it is feasible to obtain misleading data. For instance, a possible source of artifacts is the interaction between the excited photosensitizer and TEMP, which is related to the widely described quenching of photosensitizers by amines [1,[107][108][109]. The aim of the present study is to compare the results obtained by the direct detection (TRNIR method) and by indirect spin trapping (TEMPO/EPR method) for the detection and quantification of singlet oxygen, using a set of well-known photosensitizers.…”
Section: Production Ofmentioning
confidence: 99%
“…Photoinduced electron transfer (PET) is a feasible reaction between ketone or aromatic hydrocarbon photosensitizers and amines [1,[107][108][109]. Being a secondary amine, TEMP (E ox = 1.0 V vs SCE) [117] could be oxidized by PET if the process is thermodynamically allowed.…”
Section: Electron Transfer Oxidation Of Temp To Tempomentioning
confidence: 99%