Department of Chemistry, Indiana University, 800 E. Kirkwood Avenue, Bloomington, Indiana47405, United States.
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 36, 48149Münster, Germany.
J Am Chem Soc. 2022 Sep 28;144(38):17680-17691. doi: 10.1021/jacs.2c07726. Epub 2022 Sep 15.
Photochemical dearomative cycloaddition has emerged as a useful strategy to rapidly generate molecular complexity. Within this context, stereo- and regiocontrolled intermolecular -cycloadditions are rare. Herein, a method to achieve photochemical cycloaddition of quinolines and alkenes is shown. Emphasis is placed on generating sterically congested products and reaction of highly substituted alkenes and allenes. In addition, the mechanistic details of the process are studied, which revealed a reversible radical addition and a selectivity-determining radical recombination. The regio- and stereochemical outcome of the reaction is also rationalized.
光致非芳构化环加成已成为快速生成分子复杂性的有用策略。在这种情况下，立体和区域控制的分子间环加成很少见。本文展示了一种实现喹啉和烯烃光化学环加成的方法。重点是生成空间拥挤的产物，以及高取代烯烃和丙二烯的反应。此外，还研究了该过程的机理细节，揭示了可逆的自由基加成和选择性决定的自由基重组。反应的区域和立体化学结果也得到了合理的解释。
