Recent Advances in Chan-Evans-Lam Coupling Reaction

Chan-Evans-Lam reaction has been served as a powerful cross-coupling reaction in organic synthesis since its discovery in the 1990s owing to the feature of mild reaction conditions, functional group tolerance and open-flask chemistry.Up to now, it has been not only extensively utilized in carbon-heteroatom or carbon-carbon bonds formation, but also successfully applied to synthesize natural products and alkaloids.The new strategies of Chan-Evans-Lam reaction in organic synthesis as well as applications in total synthesis in recent five years are discussesed.Keywords coupling reaction; copper-catalyzed; organic boron reagents; carbon-heteroatom bond formation 近年来, 过渡金属催化的氧化交叉偶联反应已经被 证明是构建碳-碳键、碳-杂键最有效和最直接的策略之 一, 在医药、农药、染料及日用化工品等领域中都起到 了非常重要的作用 [1,2] .1998 年, Chan、Evans 和 Lam 三 个课题组 [3] 分别独立地报道了铜盐促进下不同杂原子作 为亲核试剂与芳基硼酸进行偶联反应构建碳-杂键的方 法. 与其它过渡金属(如钯、镍等)参与的偶联反应相比, 此类反应具有铜盐价格便宜(铜金属约 0.01 美元/克, 而 钯金属约 350 美元/克)、反应条件温和、不需要复杂配 体、操作简便、在空气氛围中搅拌就能顺利进行等特点 [4] .因此, 铜盐促进不同原子类型的亲核试剂与有机硼 试剂进行的偶联反应被称之为 Chan-Evans-Lam 偶联反 应 [5] , 此反应由于在空气中就能进行, 又被称为 openflask Chemistry (Eq.1).