Tan Guangying, Das Mowpriya, Maisuls Iván, Strassert Cristian A, Glorius Frank
Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149, Münster, Germany.
Institut für Anorganische und Analytische Chemie, CeNTech, CiMIC, SoN, Westfälische Wilhelms-Universität Münster, Heisenbergstrasse 11, 48149, Münster, Germany.
Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15650-15655. doi: 10.1002/anie.202105355. Epub 2021 Jun 4.
The C-C bond formation reaction represents a fundamental and important transformation in synthetic chemistry, and exploring new types of C-C bond formation reactions is recognized as appealing, yet challenging. Herein, we disclose the first example of rhodium-catalyzed dealkenylative arylation of alkenes with arylboronic compounds, thereby providing an unconventional access to bi(hetero)aryls with excellent chemoselectivity. In this method, C(aryl)-C(alkenyl) and C(alkenyl)-C(alkenyl) bonds in various alkenes and 1,3-dienes can be cleaved via a hydrometalation and followed by β-carbon elimination pathway for Suzuki-Miyaura reactions. Furthermore, a series of novel organic fluorescent molecules with excellent photophysical properties has been efficiently constructed with this protocol.
碳-碳键形成反应是合成化学中一种基本且重要的转化反应，探索新型碳-碳键形成反应被认为很有吸引力，但也具有挑战性。在此，我们报道了首例铑催化烯烃与芳基硼酸化合物的脱烯基芳基化反应，从而为具有优异化学选择性的双（杂）芳基化合物提供了一种非常规的合成方法。在该方法中，各种烯烃和1,3-二烯中的碳（芳基）-碳（烯基）键和碳（烯基）-碳（烯基）键可通过氢金属化作用断裂，随后通过β-碳消除途径进行铃木-宫浦反应。此外，利用该方法已高效构建了一系列具有优异光物理性质的新型有机荧光分子。
