1997
DOI: 10.1016/s0040-4020(97)00119-1
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Photoinduced electron transfer reactions of benzyl phenyl sulfides promoted by 9,10-dicyanoanthracene

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Cited by 69 publications
(49 citation statements)
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“…These radicals then react to generate the charge separated persulfoxide ('S + OO À ') intermediate 15, which then reacts with another equivalent of thioanisole to deliver the sulfoxide product 11. [48] This mechanism is supported by previous studies showing that direct electron transfer from a substrate to singlet oxygen can lead to generation of radical ions, [36,[49][50] as well as control reactions we performed with diphenylsulfoxide [51][52][53] which confirm the formation of persulfoxide intermediate 15 when using catalysts 1 or 3 (see the Supporting Information for more details, Table S9 and S10). In addition, oxidation processes that proceed via the charge separated intermediate 15 are known to be promoted by polar solvents due to charge stabilisation, [46,[54][55][56] and thus the poor reactivity we observed in non-polar toluene (Table S11) further supports the pathway shown in Scheme 1.…”
Section: Resultssupporting
confidence: 85%
“…These radicals then react to generate the charge separated persulfoxide ('S + OO À ') intermediate 15, which then reacts with another equivalent of thioanisole to deliver the sulfoxide product 11. [48] This mechanism is supported by previous studies showing that direct electron transfer from a substrate to singlet oxygen can lead to generation of radical ions, [36,[49][50] as well as control reactions we performed with diphenylsulfoxide [51][52][53] which confirm the formation of persulfoxide intermediate 15 when using catalysts 1 or 3 (see the Supporting Information for more details, Table S9 and S10). In addition, oxidation processes that proceed via the charge separated intermediate 15 are known to be promoted by polar solvents due to charge stabilisation, [46,[54][55][56] and thus the poor reactivity we observed in non-polar toluene (Table S11) further supports the pathway shown in Scheme 1.…”
Section: Resultssupporting
confidence: 85%
“…Oxygenation of sulfides through visible-light strategies have attracted wide research interestf rom organic and inorganic chemists since the last century.As eries of organic sensitizers including N-methylquinolinium tetrafluoroborate, [36] 9,10-dicyanoanthracene, [37] rose bengal, [38] 2,4,6-triphenylpyrylium tetrafluoroborate, [39] 4,4-difluoro-4-bora-3a,4a-diaza-s-indancene (BODIPY) [40] andmethyl blue [41] have been investigated. However,m ost of them produced am ixture of sulfoxides ands ulfones, and aldehydes were also detected as by-products in some cases.I n2 013, Yaoa nd co-workers reported as imple metal-free catalytic oxygenation of sulfides under visiblel ight and air,w ith high chemoselectivity.D uring reaction optimizations, they found the solvent was crucial for the selectivity;f or example, ethanol and methanols howed ag reat difference in selectivity.I na ddition, hydrogen chloride played ap romoter role for the efficiency (Scheme 19).…”
Section: Formation Of S=obondsmentioning
confidence: 99%
“…110 It should be noted that bromination of thiophenes is particularly important in the preparation of oligothiophenes and polythiophenes, [111][112][113][114][115][116][117][118][119][120][121][122][123] which have many applications as conductive, semiconductive, nonlinear optical and liquid crystalline materials. 124 Visible light irradiation of [Acr + -Mes]ClO 4 -(λ max = 430 nm, 0.20 mM) in an oxygen-saturated MeCN solution containing 1,2,4-trimethoxybenzene (TMB, 4.0 mM), 50 % aqueous HBr ([HBr] = 20 mM, [H 2 O] = 100 mM) with a xenon lamp attached with color glass filter (λ < 320 nm) for 20 min resulted in formation of a brominated product, 2,4,5trimethoxybromobenzene.…”
Section: Photocatalytic Bromination Via Charge-separationmentioning
confidence: 99%