Phosphine Organocatalysis.

Phosphine Organocatalysis.
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膦有机催化

DOI:
10.1021/acs.chemrev.8b00081
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发表时间:
2018-10-24
期刊:
影响因子:
62.1
通讯作者:
Kwon O
Kwon O
中科院分区:
化学1区
文献类型:
--
作者:
Guo H;Fan YC;Sun Z;Wu Y;Kwon O

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亲核膦催化的标志是膦与亲电子起始材料的初始亲核加成,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,我们根据亲电组分对亲核膦催化反应进行了分类。在大多数情况下,这些亲电试剂具有碳-碳多重键:烯烃(第2节)、丙二烯(第3节)、炔(第4节)和Morita-Baylis-Hillman(MBH)醇衍生物(MBHAD;第5节)。在这些部分中的每一个中,反应是基于第二起始材料的性质编译的-亲核试剂、双核试剂、亲电试剂和亲电试剂-亲核试剂。通过初始添加到不具有碳-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。虽然膦不具有催化作用,但膦与含碳-碳多重键的化合物的亲核加成形成叶立德与催化作用密切相关,并在第7节中进行了讨论。最后,第8节汇编了各种主题,包括Hüisgen Zwittons的环化,膦介导的还原,亚氨基膦有机催化,以及经典氧化膦生成反应的催化变体。
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.
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期刊: ORGANIC LETTERS
影响因子: 5.2
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