Boldrini Cosimo, Reis Marta Castiñeira, Harutyunyan Syuzanna R
Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
J Org Chem. 2022 Oct 7;87(19):12772-12782. doi: 10.1021/acs.joc.2c01331. Epub 2022 Sep 12.
In this work, we demonstrate how allylative dearomatization of benzyl chlorides can provide direct access to a variety of semibenzenes. These scaffolds behave as highly reactive nucleophiles in the presence of carbocations. In addition, semibenzenes are susceptible to intramolecular rearrangements rendering a broad scope of functionalized arenes. An analysis of this new reactivity is reported, as well as the rationale behind the observed intramolecular reorganizations.
在这项工作中，我们展示了苄基氯的烯丙基化去芳构化反应如何能够直接合成多种半苯。在碳正离子存在下，这些骨架表现为高活性亲核试剂。此外，半苯易于发生分子内重排，从而产生多种官能化芳烃。本文报道了对这种新反应性的分析，以及所观察到的分子内重排背后的原理。
