Synthesis and Reactions of 3,3-Difluoro-2-exo-methylidene Indolines
Synthesis and Reactions of 3,3-Difluoro-2-exo-methylidene Indolines
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3,3-二氟-2-外亚甲基二氢吲哚的合成与反应
DOI：
10.1021/acs.orglett.0c01175
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发表时间：
2020
期刊：
影响因子：
5.2
通讯作者：
M. Lautens
中科院分区：
文献类型：
--
作者：
Nicolas Zeidan;Matthew P Zambri;Sven Unger;Christian Dank;Alexa Torelli;Bijan Mirabi;M. Lautens
报道了2-甲基吲哚的去芳香化亲电氟化反应，得到了含外亚甲基的3，3-二氟吲哚。模型底物是在高达20 mmol的规模上合成的，并通过实际的重结晶得到提纯，成为一种稳定的、但具有活性的结晶固体。烯烃是两性的，既可以作为亲核剂，也可以作为亲核剂。探索了广泛的无金属、钯、铑和铜反应，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。
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.