- Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis
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A practical and efficient method is established for the direct oxidative lactonization of the C(sp3)-H bonds relying on visible-light-induced photoredox catalysis. This protocol expediently allows the delivery of diverse phthalides using oxygen as the sole terminal oxidant under metal-free conditions at room temperature. Notably, the choice of an appropriate hydrogen atom transfer (HAT) cocatalyst is revealed to be critical for the success of this process.
- Cai, Shunyou,Cai, Zhixiong,Chen, Shanyi,Huang, Mingqiang,Lai, Qihong,Lin, Yulin,Liu, Chao,Liu, Hui
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p. 8212 - 8216
(2021/10/29)
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- Facile synthesis of phthalides from methyl ortho-iodobenzoates and ketones via an iodinemagnesium exchange reaction using a silylmethyl Grignard reagent
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Phthalides have been easily prepared by the treatment of methyl o-iodobenzoates with a silylmethyl Grignard reagent in the presence of ketones. The electron-withdrawing ester moiety of methyl o-iodobenzoates and the low nucleophilicity of the silylmethyl Grignard reagent prompted a smooth iodinemagnesium exchange reaction, at room temperature, without affecting the ester moiety or resulting in an undesired reaction with electrophilic ketones. This simple method, wherein special control of the reaction temperature was unnecessary, has allowed the synthesis of various phthalides, including a phenolphthalein derivative.
- Nakamura, Yu,Yoshida, Suguru,Hosoya, Takamitsu
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supporting information
p. 858 - 861
(2017/06/13)
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- INVESTIGATION OF THE STRUCTURE OF 3,3-DIALKYL(ARYL)PHTHALIDES AND 3,3-DIALKYL(ARYL)THIOPHTHALIDES BY IR SPECTROSCOPY
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In 3,3-dialkyl(aryl)phthalides and the corresponding thiophthalides the frequencies of the stretching vibrations of the carbonyl group correlate with the sum of the Taft ?* induction constants of the substituent at C3 of the heterocycle.The substitution of oxygen in the ring by sulfur substantially reduces the frequency of the carbonyl stretching vibrations.
- Oparin, D. A.,Melent'eva, T. G.,Pavlova, L. A.
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p. 2149 - 2151
(2007/10/02)
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