Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Wien, Austria.
Angew Chem Int Ed Engl. 2017 May 15;56(21):5921-5925. doi: 10.1002/anie.201701538. Epub 2017 Apr 21.
Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called "natural", polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C-C coupling.
许多当代有机合成依赖于由化学键和反应中心固有、所谓的“自然”极性驱动的转化。非传统极化合成子的设计是一种非常可取的策略，因为它通常能够为复杂物质的合成提供前所未有的逆合成切断。虽然羰基中心的反转是一种众所周知的策略，但羰基α位的极性反转要少见得多。在此，我们报告了一种新型亲电烯醇翁物种的设计及其在高效和选择性、无金属氧化 C-C 偶联中的应用。
