转鼓
电泳剂
亲核细胞
烷基
化学
杂原子
组合化学
有机合成
有机化学
催化作用
作者
Kaluvu Balaraman,Christian Wolf
出处
期刊:Science Advances
[American Association for the Advancement of Science (AAAS)]
日期:2022-05-27
卷期号:8 (21)
被引量:7
标识
DOI:10.1126/sciadv.abn7819
摘要
The widespread use of fluorinated organic compounds in the health, agrochemical, and materials sciences is sustained by a steadily growing pool of commercially available fine chemicals. The synthetic utility of the increasingly ubiquitous Csp 3 ─F bond, however, remains to be fully exploited, which is often a difficult task because of its paramount stability and chemical inertness. Here, we demonstrate chemodivergent activation of monofluoroalkyl compounds toward either nucleophilic or electrophilic intermediates. This is accomplished under conditions that are compatible with several reaction types and many functional groups, which drastically widens the current scope of organofluorine chemistry and sets the stage for carbon-carbon and carbon-heteroatom bond formations, stereoselective construction of bisoxindole alkaloid scaffolds via in situ Umpolung, and cross-electrophilic coupling methodology. The selective generation of either nucleophilic or electrophilic species and the possibility of doing so simultaneously or, alternatively, switching molecular polarity enable previously unidentified synthetic opportunities that recognize alkyl fluorides as chemodivergent building blocks.
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