- Electrochemical intramolecular haloheterocyclization reactions using 1,2-dihaloethanes as halogenating reagents
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Electrochemistry has a lot of inherent advantages in organic synthesis and many cyclization reactions have been achieved under electrochemical conditions. However, the electrochemical intramolecular haloheterocyclization of N-alkenylamides using bulk and common chemicals such as 1,2-dihaloethanes as halogenating reagents are less studied. Herein, we have developed an electrochemical intramolecular haloheterocyclization of N-alkenylamides to prepare 2-oxazolines, 2-thiazolines, 1,3-oxazines and isoxazolines using readily available 1,2-dihaloethanes as halogenating reagents. This protocol is a convergent strategy integrating several reactions, such as N-alkenylamide chlorooxygenation, chlorosulfuration, bromooxygenation and bromosulfuration. The reaction avoids the use of catalysts, reductants, oxidants, metal salts and iodine reagents, which makes it more sustainable and renewable.
- Gu, Li-Jun,Li, Ming,Li, Xiangguang,Liu, Yang,Zhang, Chi,Zhao, Na,Zhou, Ya-Qin
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supporting information
(2021/12/30)
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- Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of Allylic Oximes: Synthesis of Trifluoromethylated Isoxazolines
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Cheap and commercially available trichloroisocyanuric acid has been used to promote trifluoromethylation by using TMSCF3 as the trifluoromethyl source. The method provides a novel and efficient protocol for the construction of CF3-containing 4,5-dihydroisoxazoles from allylic oximes in good to excellent yields.
- Zhang, Weigang,Su, Yingpeng,Wang, Ke-Hu,Wu, Lili,Chang, Bingbing,Shi, Ya,Huang, Danfeng,Hu, Yulai
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p. 376 - 379
(2017/04/21)
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- Transition-metal-free oxychlorination of alkenyl oximes:: In situ generated radicals with tert -butyl nitrite
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Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has be
- Zhang, Xiao-Wei,Xiao, Zu-Feng,Wang, Mei-Mei,Zhuang, Yan-Jun,Kang, Yan-Biao
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p. 7275 - 7281
(2016/08/05)
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- Oxime-mediated oxychlorination and oxybromination of unactivated olefins
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An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.
- Dong, Kui-Yong,Qin, Hai-Tao,Liu, Feng,Zhu, Chen
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p. 1419 - 1422
(2015/03/04)
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