An efficient iodine pentoxide-triggered iodocarbocyclization for the synthesis of iodooxindoles in water

作者：Zhang, Ming-Zhong^*; Wang, Xin; Gong, Ming-Ying; Chen, Lin; Shi, Wen-Bing^*; He, Shu-Hua; Jiang, Yong; Chen, Tieqiao^*

来源：Organic and Biomolecular Chemistry, 2018, 16(28): 5197-5202.

DOI：10.1039/c8ob01130c

• METAL-FREE SYNTHESIS
• MEDIATED ELECTROPHILIC CYCLIZATION
• ACTIVATED ALKENES
• N-ARYLACRYLAMIDES
• SODIUM TRIFLUOROMETHANESULFINATE
• SUBSTITUTED QUINOLINES
• CONTAINING OXINDOLES
• INTRAMOLECULAR ARYLATION
• ALKYNES
• TRIFLUOROMETHYLATION

An efficient iodocarbocyclization of alkenes for the synthesis of iodooxindoles has been developed. This reaction proceeds in a chemoselective manner and shows excellent tolerance of various functional groups, including a chemosensitive hydroxymethyl group. Nonmetal inorganic iodine pentoxide was used as both the oxidant and iodine source, making this protocol very practical. On the basis of experimental observations, a plausible electrophilic reaction mechanism was proposed.

• 出版日期2018-7-28
• 单位海南大学; 长江师范学院