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钯/铜催化的芳基碘化物与偕二氟烯烃的脱氟羰基偶联反应:α-氟查耳酮的高效合成

Pd/Cu-Catalyzed Defluorinative Carbonylative Coupling of Aryl Iodides and gem-Difluoroalkenes: Efficient Synthesis of α-Fluorochalcones.

作者信息

Wu Fu-Peng, Yuan Yang, Liu Jiawang, Wu Xiao-Feng

机构信息

Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Straße 29a, 18059, Rostock, Germany.

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 116023, Dalian, Liaoning, China.

出版信息

Angew Chem Int Ed Engl. 2021 Apr 12;60(16):8818-8822. doi: 10.1002/anie.202017365. Epub 2021 Mar 9.

Abstract

An unprecedented and challenging defluorinative carbonylation was achieved. Enabled by a Pd/Cu cooperative catalyst system, the first example of defluorinative carbonylative coupling has been established. With gem-difluoroalkenes and aryl iodides as the substrates, this methodology offers flexible and facile access to privileged α-fluorochalcones under mild reaction conditions in moderate-to-excellent yields. Mechanistic studies indicated transmetalation between palladium and copper intermediates as a crucial step of the catalytic cycle.

摘要

实现了一种前所未有的且具有挑战性的脱氟羰基化反应。在钯/铜协同催化体系的作用下,建立了首例脱氟羰基化偶联反应。以偕二氟烯烃和芳基碘化物为底物,该方法在温和的反应条件下,以中等到优异的产率,提供了一种灵活便捷的途径来合成具有特殊结构的α-氟查耳酮。机理研究表明,钯和铜中间体之间的金属转移是催化循环的关键步骤。

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