14759-49-0Relevant academic research and scientific papers
Weakly coordinating group directed rhodium-catalyzed unconventional site-selective C–H olefination of indolizines at the 8-position
Feng, Xue,Tian, Jiaxin,Sun, Ying,Hu, Huayou,Lu, Mingzhu,Kan, Yuhe,Fang, Danjun,Wang, Chao
supporting information, p. 470 - 474 (2020/03/19)
A rhodium-catalyzed directing group promoted selective C–H olefination reaction of indolizines at the 8-position is reported. Di-olefination at 2,8-positions also achieved with silver hexafluoroantimonate as an additive under similar reaction conditions. Weakly coordinating groups, such as ketone, aldehyde, amide and ester, were used as directing groups. The ester group can be removed under acid conditions and therefore is used as a traceless directing group.
Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines
Liu, Yan,Hu, Huayou,Zhou, Junyu,Wang, Wenhui,He, Youliang,Wang, Chao
, p. 5016 - 5024 (2017/07/10)
Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.
