Zeidan Nicolas, Zambri Matthew, Unger Sven, Dank Christian, Torelli Alexa, Mirabi Bijan, Lautens Mark
Davenport Research Laboratories, Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
Org Lett. 2020 May 1;22(9):3688-3691. doi: 10.1021/acs.orglett.0c01175. Epub 2020 Apr 10.
A dearomative electrophilic fluorination of 2-methylindoles is reported, delivering 3,3-difluoroindolines bearing an exomethylidene. The model substrate was synthesized on up to a 20 mmol scale and was purified by a practical recrystallization as a crystalline bench-stable, yet reactive solid. The olefin is amphoteric and can react both as a nucleophile and as an electrophile. A wide range of metal-free, palladium, rhodium, and copper reactions was explored, forming new C-H, C-B, C-C (alkyl and aryl), C-N, C-O, C-P, and C-S bonds.
报道了2-甲基吲哚的脱芳构亲电氟化反应,生成带有亚甲基外取代基的3,3-二氟吲哚啉。模型底物的合成规模可达20 mmol,并通过实用的重结晶方法纯化,得到一种结晶状、易于保存且具有反应活性的固体。该烯烃具有两性,既能作为亲核试剂反应,也能作为亲电试剂反应。研究了一系列无金属、钯、铑和铜参与的反应,形成了新的C-H、C-B、C-C(烷基和芳基)、C-N、C-O、C-P和C-S键。