The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

中文翻译：

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膦有机催化

亲核膦催化的特点是膦最初亲核加成到亲电子起始材料上，通常在温和条件下产生反应性两性离子中间体。在这篇综述中，我们根据亲电成分对亲核膦催化反应进行分类。在大多数情况下，这些亲电子试剂具有碳-碳多重键：烯烃（第 2 节）、丙二烯（第 3 节）、炔烃（第 4 节）和 Morita-Baylis-Hillman (MBH) 醇衍生物（MBHAD；第 5 节） 。在每个部分中，反应都是根据第二种起始材料（亲核试剂、双亲核试剂、亲电试剂和亲电试剂-亲核试剂）的性质进行编译的。通过初始加成到不具有碳-碳多重键的起始材料中发生的亲核膦催化反应在第 6 节中进行了整理。虽然在膦中不具有催化作用，但通过膦与碳-碳多重键的亲核加成形成叶立德含键化合物与催化密切相关，并在第 7 节中讨论。最后，第 8 节汇集了各种主题，包括 Hüisgen 两性离子的环化、膦介导的还原、亚氨基正膦有机催化以及经典氧化膦生成反应的催化变体。