- 著者
-
矢内 光
- 出版者
- 公益社団法人 有機合成化学協会
- 雑誌
- 有機合成化学協会誌 (ISSN:00379980)
- 巻号頁・発行日
- vol.80, no.3, pp.186-197, 2022-03-01 (Released:2022-03-09)
- 参考文献数
- 63
- 被引用文献数
-
1
(Trifluoromethyl)sulfonyl group (Tf=CF3SO2) is one of the strongest electron-withdrawing substituents. A number of strongly acidic compounds bearing this substituent such as TfOH and Tf2NH have been reported. During a past decade, structurally similar carbon(C-H)acids “Tf2CHR” have attracted much attention as a new class of superacidic molecules, which show stronger acidity than sulfuric acid molecule, owning to excellent performance as acid catalysts in organic synthesis. Needless to say, development of such novel acids implies creation of highly stable anionic species as well. In recent years, the authors have been engaged in chemical research focusing on highly stabilised carbanions [Tf2CR]-. Here, the carbanion moiety is effectively stabilised by two Tf groups through electron-withdrawing inductive effect and negative hyperconjugation. Our effort revealed chemically inert, less coordinating, and lipophilic properties of this anion. In this account, we describe our achievements in the [Tf2CR]- chemistry including synthesis, structure, reactivity, and functions.