1689-09-4Relevant articles and documents
Lactone Formation in the Oxidation of Diols with N-Iodosuccinimide and Silver Acetate
Beebe, Thomas R.,Adkins, Rick,Baldridge, Ruth,Hensley, Vivian,McMillen, Doug,et al.
, p. 5472 - 5474 (1987)
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A new ring enlargement reaction of γ-lactones to seven-membered cyclic ethers via intramolecular endo-mode cyclisation of the ω-hydroxy allenyl ketone intermediates in situ
Nagao, Yoshimitsu,Jeong, Ill-Yun,Lee, Woo Song,Sano, Shigeki
, p. 19 - 20 (1996)
Phthalides 1a-f were treated with prop-2-ynylmagnesium bromide followed by treatment with 20% HCl in one pot to give the corresponding seven-membered cyclic ethers, benzoxepins 4a-f.
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Jones,Lavigne
, p. 2020,2022 (1960)
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Electron-Transfer-Induced Intramolecular Heck Carbonylation Reactions Leading to Benzolactones and Benzolactams
Fukuyama, Takahide,Bando, Takanobu,Ryu, Ilhyong
, p. 3015 - 3021 (2018)
A metal-catalyst-free intramolecular Heck carbonylation reaction of benzyl alcohols and benzyl amines with carbon monoxide under heating at 250 °C affords the corresponding benzolactones and benzolactams in good to excellent yields. A hybrid radical/ionic chain mechanism, involving electron transfer from radical anions generated by nucleophilic attack of alcohols or amines on intermediate acyl radicals, is proposed.
Phthalide synthesis through dehydrogenated lactonization of the C(sp3)-H bond by photoredox catalysis
Cai, Shunyou,Cai, Zhixiong,Chen, Shanyi,Huang, Mingqiang,Lai, Qihong,Lin, Yulin,Liu, Chao,Liu, Hui
supporting information, p. 8212 - 8216 (2021/10/29)
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.
Redox deracemization of α-substituted 1,3-dihydroisobenzofurans
Chen, Xiaohan,Zhao, Ran,Liu, Ziqiang,Sun, Shutao,Ma, Yingang,Liu, Qingyun,Sun, Xia,Liu, Lei
supporting information, p. 2305 - 2308 (2021/03/08)
Chiral α-substituted 1,3-dihydroisobenzofurans are key scaffolds in a number of bioactive natural products and synthetic pharmaceuticals. However, catalytic asymmetric approaches have been rarely developed. Here, a redox deracemization technology is adopted to address the catalytic asymmetric synthesis. A broad range of α-aryl substituted 1,3-dihydroisobenzofurans are effectively deracemized in high efficiency with excellent ee. α-Alkynyl substituted ethers were also compatible with the deracemization technology.